SUBSTITUTED 4-AZA!NDOLES AND THEIR USE AS GLUN2B RECEPTOR

MODULATORS

Field of the Invention

The present invention is related to compounds having NR2B

modulating properties, pharmaceutical compositions comprising these compounds, chemical processes for preparing these compounds and their use in the treatment of diseases associated with NR2B receptor activity in animals, in particular humans.

Background of the Invention

Glutamate is one of the major excitatory neurotransmitters that is widely spread in the brain. First indication of its role as an excitatory messenger was in the 1950's when it was observed that intravenous administration of glutamate induces convulsions. However, the detection of the whole glutamatergic neurotransmitter system with its various receptors did not take place before the 1970's and 1980's when numerous antagonists were developed or, as in the case of PCP and keiamine, were identified as antagonists. Finally, in the 1990's molecular biology provided the tools for the classification of the glutamatergic receptors.

N-methyi-D-aspartate (NMDA) receptors are a subtype of ionotropic glutamate receptors that mediate excitatory synaptic transmission in the brain. NMDA receptors are ubiquitously distributed thoroughout the brain and play a key role in synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition and learning. NMDA receptors are distinct from other major subtypes of ionotropic glutamate receptors (AMPA and kainate receptors) in that they are blocked by Mg ²⁺ at resting membrane potentials, are highly Ca ²⁺ permeable, and require co-activation by two distinct neurotransmitters: glutamate and glycine (or D-serine) (Trayneiis SF et a!., Pharmacol Rev, 2010; 62(3):405-96). The influx of Ca ²⁺ through NMDA receptors triggers signaling cascades and regulates gene expression that is critical for different forms of synaptic plasticity including both long-term potentiation of synapse efficacy (LTP) (Berberich S et al. , Neuropharmacology 2007; 52(1 ):77-86) and long-term depression (LTD)

(Massey, PV et al., J Neurosci. 2004 Sep 8;24(36):7821 -8).

The vast majority of the mammalian NMDA receptors form a

heterotetramer made of two obligatory GluN1 units and two variable GluN2 receptor subunits encoded by the GRIN1 gene and one of four GRIN2 genes, respectively. One or both GluN2 subunits can be potentially replaced by a

GluN3A or a GluN3B subunit. The GRINM gene product has 8 splice variants while there are 4 different GRIN2 genes (GRIN2A-D) encoding four distinct GluN2 subunits. The glycine binding site is present on the GluN1 subunit and the glutamate binding site is present on the GluN2 subunit.

The GiuNR2 subunits play a dominant role in determining the functional and pharmacological properties of the NMDA receptor assembly and exhibit distinct distribution in different areas of the brain. For instance, GluN2B subunits are expressed primarily in the forebrain in the adult mammalian brain (Paoletti P et al. , Nat Rev Neurosci. 2013; 14(6):383~4Q0; Watanabe M et al. , J Comp Neuro!. 1993; 33S(3):377-90) and are implicated in learning, memory processing, mood, attention, emotion and pain perception (Cull-Candy S et al., Curr Opin Neurobioi. 2001 ; 1 1 (3):327-35).

Compounds that modulate GluN2B-containing NMDA receptor function can be useful in treatment of many neurological and psychiatric disorders including but not limited to bipolar disorder (Martucci L et al., Schizophrenia Res, 2006; 84(2-3):214-21 ),, major depressive disorder (Miller OH et al., eLife. 2014; 3:e03581 ; Li N et al., Biol Psychiatry. 2011 ; 69(8):754-61 ), treatment-resistant depression (Preskorn SH et al. J Clin Psychopharmacoi. 2008; 28(8):831 ~7) and ther mood disorders (including schizophrenia (Grimwood S et al., Neuroreport. 1999;10(3):461 -5; Weickert CS et al. Molecular Psychiatry (2013) 18, 1 185- 1 192), ante- and postpartum depression, seasonal affective disorder and the like), Alzheimer's disease (Hanson JE et al., Neurobioi Dis. 2015; 74:254-62; Li S et al., J Neurosci. 2011 ; 31 (18):6827-38) and other dementias (Orgogozo JM et al. Stroke 2002, 33: 1834-1839), Parkinson's disease (Duty S, CNS Drugs. 2012; 26(12): 1017-32; Steece-Collier K et al., Exp Neurol. 2000; 163(1 ):239-43; Leaver KR et al. Clin Exp Pharmacol Physiol. 2008; 35(1 1 ): 1388-94),

Huntington's chorea (Tang TS et al., Proc Natl Acad Sci USA. 2005; 102(7):26Q2-7; Li L et al., J Neurophysiol. 2004; 92(5):2738-46), multiple sclerosis (Grasselii G et al., Br J Pharmacol. 2013; 168(2):502-17; Farjam M et al., Iran J Pharm Res. 2014; 13(2):695-705), cognitive impairment (Wang D et al. 2014, Expert Opin Ther Targets Expert Opin Ther Targets.

2QU;18(10):1121-30), head injury (Bullock MR et al., Ann N Y Acad Scl. 1999; 890:51 -8), spinal cord injury, stroke (Yang Y et al., J Neurosurg. 2003;

98(2):397-403), epilepsy (Naspolini AP et al., Epilepsy Res. 2012 Jun;100(1 - 2): 12-9), movement disorders (e.g. dyskinesias) (Morissette !VI et al., Mov Disord. 2006; 21 (1 ):9-17), various neurodegenerative diseases (e.g.

amyotrophic lateral sclerosis (Fuller PI et al. , Neurosci Lett. 2006; 399(1 -2): 157- 61 ) or neurodegeneration associated with bacterial or chronic infections), glaucoma (Naskar R et al. Semin Ophthalmol. 1999 Sep; 14(3): 152-8 ), pain (e.g. chronic, cancer, post-operative and neuropathic pain (Wu LJ and Zhuo M, Neurotherapeutics. 2009; 6(4):693-7G2), diabetic neuropathy, migraine (Peeters M et al., J Pharmacol Exp Ther. 2007; 321 (2):564~72), cerebral ischemia (Yuan H et al., Neuron. 2015; 85(6): 1305-18), encephalitis (Daimau J. et al., Lancet Neurol. 2008; 7(12): 1091 -8.), autism and autism spectrum disorders (Won H. et al., Nature. 2012; 486(7402):261 -5), memory and learning disorders (Tang, Y. P. et al., Nature. 1999; 401 (6748):63-9), obsessive compulsive disorder (Arnold PD et al., Psychiatry Res. 2009; 172(2): 136-9.), attention deficit hyperactivity disorder (ADHD) (Dorval KM et al., Genes Brain Behav. 2007; 6(5):444-52), PTSD (Halier J et al. Behav Pharmacol. 201 1 ;22(2):1 13-21 ; Leaderbrand K et al. Neurobiol Learn Mem. 2014; 1 13:35-40), tinnitus (Guitton MJ, and Dudai Y, Neural Plast. 2007; 80904; Hu SS et al. 2016; 273(2): 325-332), sleep disorders (like narcolepsy or excessive daytime sleepiness, patent WO 2009058261 A1 ), vertigo and nystagmus (Straube A. et al., Curr Opin Neurol. 2005; 18(1 ): 1 1 -4; Starck M et al. J Neurol. 1997 Jan;244(1 ):9-16), anxiety autoimmunological disorders like neuropsychiatric systemic lupus erythematosus (Kowal C et al. Proc. Natl. Acad. Sci. U.S.A. 2006; 103, 19854-19859) and addictive illnesses (e.g. alcohol addiction, drug addiction) (Nagy J, 2004, Curr Drug Targets CNS Neurol Disord. 2004; 3(3): 169-79.; Shen H et al., Proc Natl Acad Sci USA. 2011 ;108(48):19407-12). In view of the clinical importance of NR2B, the identification of compounds that modulate IMR2B receptor function represents an attractive avenue into the development of new therapeutic agents. Such compounds are provided herein.

The invention is directed to the general and preferred embodiments defined, respectively, by the independent and dependent claims appended hereto, which are incorporated by reference herein. One aspect of this invention concerns compounds of Formula (I):

wherein:

R is selected from the group consisting of: H, ³ H, halo, Chalky!, and C-i . 3haloalkyl;

R ² is selected from the group consisting of: phenyl optionally substituted with one, two, or three members independently selected from: halo, C-i. 5alkyi, and Ci-shaioalkyi; pyridinyl optionally substituted with halo, C-i. 5alkyi, C-i-shaloalkyl, and -CN; thiazoiyi optionally substituted with d. 5alkyi; benzothiophenyi; and thienyl optionally substituted with one, two or three members independently selected from: halo, Chalky!, and Ci- 5haloalkyl;

R ³ is selected from the group consisting of:

(a) wherein ring A is a 4-7 membered heterocycloaikyl

optionally containing an additional oxygen heteroatom selected from the group consisting of: azetidinyl optionally substituted with one or two members independently selected from the group consisting of: halo, Ci . ₅ aikyi, C-i-shaloalkyl, CH ₂ OH, Ci.. ₅ aikoxy, OH, and CN; pyrroiidinyl optionally substituted one or two members independently selected from the group consisting of: halo, d-saikyl, d-saikoxy, and OH; morpholino optionally substituted one or two d-salkyl members; piperidinyl optionally substituted with one or two members

independently selected from the group consisting of: halo, C-|.. ₅ alkyl, d-shaloaikyl, d-saikoxy, and OH; 3~azabicycio[3.1 .0]hexan-3~yi; 5- azaspiro[2,3]hexan-5-yl; and pyrroiidin-3-one; or

(b) ^Rja wherein R ^3a is H, or Ci-salky!;

and R ³ is selected from the group consisting of: d-saikyl optionally substituted with OH, halo, or OCH ₃ ; d-shaloaikyl; benzyl;

CH ₂ cyciopropyi; cyciopropyl optionally substituted with C-|.. ₅ alkyl; and cyclobutyi; or

(c) ^r3 ° wherein R ^3c is selected from the group consisting of:

cyciopropyl; cyclobutyi; pyrimidinyl optionally substituted with haio; pyridinyl; pyridazinyl; furanyl optionally substituted with d-shaioalkyi; oxazoiyi; isoxazoiyi optionally substituted with d-saikyl; oxadiazoiyi optionally substituted with d-salkyl; pyrazolyl optionally substituted with d-saikyl; friazolyl optionally substituted with d-saikyi;

tetrahydrofuranyl; tetrahydropyranyl; oxetanyl; and oxiranyl; or

(d) o ^~R3d wherein R ^3d is CH ₂ -cyclopropyi or cyclobutyi; or

(e) ^K wherein R is selected from the group consisting of: OH, d-salkyl, cyciopropyl, cyclobutyi, and phenyl optionally substituted with one halo substituent; or

(f) d-saikyl optionally substituted with OH or d- ₅ a!koxy; CH ₂ S(CH ₃ );

CH ₂ (S=0)CH ₃ ; CH ₂ (S02)CH ₃ ; and CH ₂ CH ₂ (C=0)CH ₃ ; or

(g)

and

R ⁴ is H, ² H or C _h alky! and pharmaceutically acceptable salts of compounds of Formula (I).

Further embodiments are provided by pharmaceutically acceptable salts of compounds of Formulas (I), pharmaceutically acceptable prodrugs of compounds of Formula (!), and pharmaceutically active metabolites of compounds of Formula (I),

In certain embodiments, the compounds of Formula (I) are compounds selected from those species described or exemplified in the detailed description below.

In a further aspect, the invention relates to enantiomers and

diastereomers of the compounds of Formula (I), as well as the

pharmaceutically acceptable salts.

In a further aspect, the invention relates to pharmaceutical

compositions for treating a disease, disorder, or medical condition mediated by NR2B receptor activity, comprising an effective amount of at least one compound selected from compounds of Formula (!), pharmaceutically acceptable salts of compounds of Formula (I), pharmaceutically acceptable prodrugs of compounds of Formula (I), and pharmaceutically active metabolites of Formula (I).

Pharmaceutical compositions according to the invention may further comprise one or more pharmaceutically acceptable excipients.

In another aspect, the chemical embodiments of the present invention are useful as NR2B receptor modulators. Thus, the invention is directed to a method for modulating NR2B receptor activity, including when such receptor is in a subject, comprising exposing NR2B receptor to an effective amount of at least one compound selected from compounds of Formula (I),

pharmaceutically acceptable salts of compounds of Formula (!), pharmaceutically acceptable prodrugs of compounds of Formula (I), and pharmaceutically active metabolites of compounds of Formula (I).

In another aspect, the invention is directed to a method of treating a subject suffering from, or diagnosed with a disease, disorder, or medical condition mediated by NR2B receptor activity, comprising administering to the subject in need of such treatment an effective amount of at least one compound selected from compounds of Formula (I), pharmaceutically acceptable salts of compounds of Formula (I), pharmaceutically acceptable prodrugs of compounds of Formula (!), and pharmaceutically active

metabolites of compounds of Formula (I). Additional embodiments of methods of treatment are set forth in the detailed description.

In another aspect, the method of studying isotopically labeled compounds in metabolic studies (preferably with ⁴ C), reaction kinetic studies (with, for example ² H or ³ H), detection or imaging techniques [such as positron emission tomography (PET) or single-photon emission computed tomography (SPECT)] including drug or substrate tissue distribution assays, or in radioactive treatment of patients. For example, an ⁸ F or C labeled compound may be particularly preferred for PET or SPECT studies.

Additional embodiments of this invention include methods of making compounds of Formula (I), pharmaceutically acceptable salts of compounds of Formula (I), pharmaceutically acceptable prodrugs of compounds of Formula (I), and pharmaceutically active metabolites of Formula (I).

An object of the present invention is to overcome or ameliorate at least one of the disadvantages of the conventional methodologies and/or prior art, or to provide a useful alternative thereto.

Additional embodiments, features, and advantages of the invention will be apparent from the following detailed description and through practice of the invention. Detailed Description of Invention

In one aspect, provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof,

wherein:

R is selected from the group consisting of: H, ³ H, halo, C _h alky!, and Ci- 3haioalkyl;

R ² is selected from the group consisting of: phenyl optionally substituted with one, two, or three members independently selected from: halo, C - 5alkyi, and Ci-shaloalkyl; pyridinyl optionally substituted with halo, d. 5alkyi, Ci-shaloalkyl, and -CN; thiazoiyi optionally substituted with Ci- 5alkyi; benzothiophenyi; and thienyl optionally substituted with one, two or three members independently selected from: halo, d-salkyi, and Ci- shaloalkyl;

R ³ is selected from the group consisting of:

(a) wherein ring A is a 4-7 membered heterocycloaiky

optionally containing an additional oxygen heteroatom selected from the group consisting of: azetidinyl optionally substituted with one or two members independently selected from the group consisting of: halo, Ci-saikyl, Ci-shaloalkyl, CH ₂ OH, C -saikoxy, OH, and CN;

pyrroiidinyl optionally substituted one or two members independently selected from the group consisting of: halo, C1.5alk.yl, Ci _-5 alkoxy, and OH; morpholino optionally substituted one or two Ci _-5 alkyl members; piperidinyi optionally substituted with one or two members

independently selected from the group consisting of: halo, Ci-salkyl, Ci-shaloalkyl, Ci-saikoxy, and OH; 3-azabicyclo[3.1 .0]hexan-3-yl; 5- azaspiro[2.3]hexan-5-yl; and pyrroiidin~3-one; or

(b) wherein R ^3a is H, or C _-5 alkyl; and R ³ is selected from the group consisting of: d-salkyl optionally substituted with OH, halo, or OCH ₃ ; d-shaloaikyl; benzyl;

CH ₂ cyciopropyi; cyciopropyl optionally substituted with d-salkyl; and cyciobutyl; or

(c) ^R ³⁰ wherein R ^3c is selected from the group consisting of:

cyciopropyl; cyciobutyl; pyrimidinyl optionally substituted with halo; pyridinyl; pyridazinyl; furanyl optionally substituted with d-shaioalkyi; oxazolyi; isoxazoiyl optionally substituted with d-salkyl; oxadiazoiyl optionally substituted with d -salkyl; pyrazoly! optionally substituted with d-salkyl; friazolyl optionally substituted with C _h alky!;

tetrahydrofuranyl; tetrahydropyrany!; oxetanyl; and oxiranyl; or

(d) wherein R ^3d is CH ₂ -cyciopropyi or cyciobutyl; or

(e) wherein R ^3e is selected from the group consisting of: OH, d -salkyl, cyciopropyl, cyciobutyl, and phenyl optionally substituted with one halo substituent; or

(f) d-salkyl optionally substituted with OH or d-salkoxy; CH ₂ S(CH ₃ );

CH ₂ (S=O)CH ₃ ; CH ₂ (SO ₂ )CH ₃ ; and CH ₂ CH ₂ (C=Q)CH ₃ ; or

(g)

An additional embodiment of the invention is a compound of Formula (I) wherein R ¹ is H, CI, Br, F, or CH ₃ .

An additional embodiment of the invention is a compound of Formula (I) wherein R ¹ is H.

An additional embodiment of the invention is a compound of Formula (\) wherein R ¹ is CI. An additional embodiment of the invention is a compound of Formula (I) wherein R ¹ is CH ₃ .

An additional embodiment of the invention is a compound of Formula (I) wherein R ² is phenyl optionally substituted with one, two, or three members independently selected from: CI, F, CH ₃ , CH ₂ CH _3i CF ₂ H, and CF ₃ ; pyridinyi optionally substituted with F, CM, CH ₃ and CF ₃ ; thiazoiyi optionally substituted with CH ₃ ; benzothiophenyl; and thienyl optionally substituted with one, two or three members independently selected from: CI, CH ₃ , CH ₂ CH ₃ , CHF ₂ and CF ₃ .

An additional embodiment of the invention is a compound of Formula

(I) wherein R ² is phenyl, 2-methylphenyl, 3-metby!phenyi, 4-methylphenyl, 3- ethyiphenyl, 3-(difluoromethyl)phenyi, 3-(trifluoromethyl)phenyl, 3,5- dimethylphenyi, 2,3-dimethylphenyl, 2~fluorophenyi, 3~fluorophenyi, 3~ chlorophenyl, 4-fiuorophenyi, 2,3-difiuorophenyi, 2,4-difluorophenyl, 3,4- difiuorophenyl, 3,4-dichlorophenyl, 2,5-difiuorophenyi, 3,5-difluorophenyi, 3- chloro-2-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-methyl-phenyl, 4- fiuoro-2-methyl-phenyi, 2-methyl-3-(trifluoromethyl)phenyl, 2-fiuoro-3- (trifluoromethyl)phenyl, 4-fluoro-3-(trifluoromethyl)phenyl, 4-fluoro~3-m ethyl- phenyl, 2-fluoro-5-methyl-phenyl, 4-fluoro-2,3-dimethyl-phenyl, 2,4-difiuoro-3- methyl-phenyl, 2,6-difiuoro-3-methyi-phenyi, 2,3,4-trifluorophenyl, 3,4,5- trifluorophenyl, 2-thienyl, 3-thienyl, 5-methyl-2-thienyi, 4-methyl-2-thienyl, 5- ethyi-2-thienyl, 5-chloro-2-thienyi, 3-chloro-2-thienyl, 4-chloro-2-thienyi, 5- chioro-3-thienyi, 5-(difluoromethyl)-2-thienyl, 5-(trifluoromethyl)-2-thienyl, 2,5- dimethyl-3-thienyl, 2,5~dichioro~3-thienyi, 5-chioro-4~methyl-2~thienyi, 2,4,5- trimethyl-3-thienyl, 6-thiazol-5-yl, 2-methylthiazol-5-yi, 6-methyl-3-pyridyi, 6- fluoro-3-pyridyl, pyridine~2-carbonitrile, 2-(trifluoromethyl)-4-pyridyl, 5~

(trifluoromethyl)-3-pyridyl, 6-(trifluoromethyl)-2-pyridyl, or benzothiophen-2-yl.

An additional embodiment of the invention is a compound of Formula (I) R ² is phenyl or thienyl, wherein the phenyl or thienyl is optionally

substituted with one, two, or three members independently selected from: halo, Ci-salkyl, and C-i-shaloalkyl. An additional embodiment of the invention is a compound of Formula

(I) wherein R is , wherein ring A is

An additional embodiment of the invention is a compound of Formula

(I) wherein R ³ is

An additional embodiment of the invention is a compound of Formula

(\) wherein R is

An additional embodiment of the invention is a compound of Formula

OH

(I) wherein R ³ is^^-^ ^{" v} , CH ₂ S(CH3), CH2(S—Q)CH3, CH ₂ (S0 ₂ )CH _3! or CH ₂ CH ₂ (C==0)CH ₃ .

An additional embodiment of the invention is a com ound of Formula

An additional embodiment of the invention is a compound of Formula

(I) wherein R is , or

An additional embodiment of the invention is a compound of Formula (I) R ⁴ is H.

An additional embodiment of the invention is a compound of Formula (I) wherein R ⁴ is CH ₃ ,

An additional embodiment of the invention is a compound of Formula (I) having the Formula (II):

wherein

R is selected from the group consisting of: H, ³ H, halo and C _h alky!;

R ² is selected from the group consisting of: phenyl optionally substituted with one, two, or three members independently selected from: halo, Ci- 5alkyi, and Ci.. ₅ haloalkyl; pyridinyl optionally substituted with halo, Ci. 5alkyi, C _-5 haloaikyl, and CN; thiazoiyi optionally substituted with Ci_ 5alkyi; and thienyl optionally substituted with halo, or C _h alky!;

ring A is selected from the group consisting of:

and R ⁴ is H, ² H, or CH ₃ ;

and pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (II).

An additional embodiment of the invention is a compound of Formula (I) having the Formula (ΠΑ):

(HA) wherein

R ^2a is H, or F;

R ² is H, F, CH ₃ or CH ₂ CH ₃ ;

R ^2c is H, F or CH ₃ ;

R ^2f is H, F, or CH ₃ ; and

R ³ is

and pharmaceuiicaily acceptable salts, N-oxides or solvates of compounds of Formula (I lA).

An additional embodiment of the invention is a compound of Formula (!) having the structure of Formula (!IB):

N

(MB)

wherein

R ^2d is H, CI, CH ₃ or CF ₃ ;

R ^2e is H or CH ₃ ; and

R ³ is

and pharmaceutically acceptable saits, N-oxides or solvates of compounds of Formula (MB). An additional embodiment of the invention is a compound of Formula (I) having the structure of Formula (III):

wherein

R is H, ³ H, halo, Chalky!, or d-shaloalkyl;

R ² is selected from the group consisting of: phenyl optionally substituted with one, two, or three members independently selected from: halo, C-i. 5alkyl, and Ci-shaioalkyi; pyridinyl optionally substituted with Ci.

shaloalkyl; benzothiophenyl; and thienyl optionally substituted with one, two, or three members independently selected from halo, Chalky!, or Ci-shaioalkyi;

R ^3a is H, or Ci- ₅ alkyl;

R ³ is selected from the group consisting of: C halky! optionally substituted with OH or OCH ₃ ; Ci-shaioalkyl; benzyl; CH ₂ cyciopropyi; cyclopropyl optionally substituted with Chalky!; and cyclobutyi; and

R ⁴ is H, H ² , or CH ₃ ;

and pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (III).

An additional embodiment of the invention is a compound of Formula (I) having the structure of Formula (IV):

R is H, or halo;

R ² is phenyl optionally substituted with one, or two members

independently selected from: halo, Ci _-5 alkyi, and Ci _-5 haioalkyi; or thienyl substituted with C-i-salkyl;

and R ⁴ is H;

and pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (IV).

An additional embodiment of the invention is a compound of Formula (I) having the structure of Formula (V):

wherein

R ¹ and R ⁴ are H;

R is phenyl optionally substituted with two halo; and

R is cyclobutyl, or CH ₂ -cyclopropyl;

and pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (V),

An additional embodiment of the invention is a compound of Formula (I) having the structure of Formul

R is H or halo;

R ² is phenyl optionally substituted with one, two, or three members

independently selected from: halo, Ci-salkyl, and d-shaioalkyi; or fhienyl substituted with halo or Ci _-5 aikyl; R is selected from the group consisting of: OH, d-salkyl, cyclopropyi, cyclobutyl, and phenyl optionally substituted with one halo substituent; and

R ⁴ is H or CH ₃ ;

and pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (VI).

A further embodiment of the current invention is a compound as shown below in Table 1 .

Example # Compound Name

10 2-[3-Chloro-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-N-cyclopropyl- acetamide;

1 1 1 -(Azetidin-I -yl)-2~(3-bromo~6~phenyl~pyrrolo[3,2~b]pyridin-1 - yl)ethanone;

12 2-[3-Chloro-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrroiidin-1 - y!-ethanone;

13 2-[3-Ch!oro-6-(m-toly!)pyrrolo[3,2-b]pyridin-1 -yl]-1 -morpholino- ethanone;

14 2-(3-Bromo-6-phenyl-pyrroio[3,2-b]pyridin-1 -yi)-N-cyclopropyl- aceiamide;

15 2-(3-Bromo-6-phenyi-pyrrolo[3,2-b]pyridin-1 -y!)-1 -pyrrolidin-1 - yl-ethanone;

16 2-(3-Bromo-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 -morpholino- eihanone;

17 2-[3-Bromo-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N- cyciopropyl-acetamide;

18 1 -(Azetidin-1 -yl)-2-[3-bromo-8-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone;

19 2-[3-Bromo-6-(4-fiuorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -y!]-1 - pyrrolidin-1 -yl-ethanone;

20 2-[3-Bromo-6-(4-fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -yl]-1 - morpholino-ethanone;

21 2-[3-Bromo-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-N-cyclopropyl- acetamide;

1 -(Azetidin-1 -yl)-2-[3-bromo-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yl]ethanone; Example # Compound Name

23 2-[3-Bromo-8-(m-iolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 - yl-eihanone;

24 2-[3-Bromo-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -morpholino- eihanone;

25 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3 _! 2-b]pyridin-1 - y!]-1 -(3,3-difluoroazetidin-1 -yl)eihanone;

26 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - yl]-1 -(3-fluoroazeiidin-1 -yl)ethanone;

27 2-[6-(4-Fluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrro!idin-1 -yl-eihanone;

28 2-[6-(4-Fluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]-1 - morpholino-ethanone;

29 1 -(Azei!din-1 -yl)-2-[3-chloro-6-(3,4-difluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone;

30 2-[3-Chloro-6-(3,4-difluorophenyl)pyrro!o[3,2-b]pyridin-1 -yl]-1 - (3-fluoroazetidin-1 ~yl)ethanone;

31 2-[6-(4-Fluorophenyl)-2-methyl-pyrrolo[3,2-b]pyridin-1 -yl]-1 - morpholino-ethanone;

32 N-Cyclopropyl-2-[6-(4-f!uorophenyl)-3-meihy!-pyrrolo[3,2- b]pyridin~1 -yl]aceiamide;

33 1 -(Azetidin-1 -yl)-2-[6-(4-fluorophenyl)-3-methyl-pyrrolo[3,2- b]pyridin-1 -yljethanone;

34 2-[3-Chloro-6-(3,4-difluorophenyl)pyrro!o[3,2-b]pyridin-1 -yl]-1 - (3,3-difluoroazetidin-1 ~yl)ethanone;

35 2-[3-Chloro-6-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3, 2- b]pyridin-1 -yl]-1 -(3-fluoroazetidin-1 -yl)ethanone; Example # Compound Name

36 2-[3-Chloro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyrid in-1 - yl]-1 -(3,3-difiuoroazetidin~1 -yl)ethanone;

37 2-[6~(4-Fluorophenyl)~2-methyl~pyrroio[3,2-b]pyridin~1 -yl]-1 - pyrrolidin-1 -yl-ethanone;

38 N-Cyclopropyl-2-[6-(4-fluorophenyl)-2-methyl-pyrrolo[3,2- b]pyridin-1 -yl]acetamide;

39 2-[3-Chloro-6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-

1 -(3-fluoroazetidin-1 -yl)ethanone;

40 2-[3-Chloro-6-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3, 2- b]pyridin-1 -yl]-1 -(3,3-dif!uoroazetidin-1 -yl)ethanone;

41 1 -(Azetidin-1 -yl)-2-[2-methyl-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yljeihanone;

42 2-(2-Methyl-6-phenyl-pyrroio[3,2-b]pyridin-1 -yl)-1 -pyrrolidin-1 - yl-ethanone;

43 N-Cyclopropy!-2-(2-methyl-6-phenyl-pyrrolo[3 _! 2-b]pyridin-1 - yl)acetamide;

44 2-[2-Methyi-6-(m-iolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 - yl-ethanone;

45 2-[2-Methyl-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -morpholino- ethanone;

46 1 -(Azetidin-1 -yl)-2-[6-(4-fluorophenyl)-2-methyl-pyrrolo[3,2- b]pyridin-1 -yljethanone;

47 1 -(Azetidin-1 -yl)-2-(2-methyl-6-phenyi-pyrrolo[3,2-b]pyridin-1 - yhethanone;

48 2-[3-Chloro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyrid in-1 - yl]-1 -(3-fluoroazetidin-1 -yi)ethanone; Example # Compound Name

49 2-[3-Chioro-6-(3,4,5-irifiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]- 1 -(3,3-difluoroazeiidin-1 -y!)eihanone;

50 2-[3~Cbtoro-6~(2,3,4~trifluorophenyl)pyrrolo[3,2~b]pyridiri- 1 ~yl]- 1 -(3,3-difluoroazetidin-1 -yl)etbanone;

51 N-Cyclopropyl-2-[2-methyl-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - y!jacetamide;

2-(2-Methyl-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 -morpholino- ethanone;

53 2-[3-Chioro-6-(m-iolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3,3- dif!uoroazetidin-l -yljethanone;

54 2-[3-Cbloro-6-(m-io!yl)pyrro!o[3,2-b]pyridin-1 -yl]-1 -(3- fluoroazeiidin-1 -yl)ethanone;

55 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3,3- difluoroazeiidin-1 -y!)eihanone;

56 2-(3-Chloro-6-phenyl-pyrro!o[3,2-b]pyridin-1 -yl)-1 -(3- fluoroazetidin~1 -yl)ethanone;

57 2-[3-Chioro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3,3- dif!uoroazetidin-1 -yl)ethanone;

58 2-[3-Cbloro-6-(4-f!uorophenyl)pyrrolo[3,2-b]pyridin-1 -y!]-1 -(3- fluoroazetidin-1 ~yi)ethanone;

59 3-[[6-(4-Fluoro-2-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 - yl]methyl]-5-methyl-isoxazole;

60 5-Methyl-3-[[6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyri din-1 - yljmeihyljisoxazole;

61 5-Methyl-3-[[6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yljmethyljisoxazo!e trifluoroacetaie salt; Example # Compound Name

62 5-Methyl-3-[[6-(o-tolyl)pyrrolo[3,2-b]pyridin-1 - yljmeihyljisoxazole irifluoroaceiaie salt;

63 3-[[6~(4-Fiuoro~3-methyl~phenyi)pyrrolo[3,2~b]pyridin~1 - yl]methyl]-5-methyl-isoxazole trifluoroacetaie salt;

64 3-[[6-(3,5-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]methyl]-5- meihy!-isoxazo!e trifluoroacetaie salt;

65 3-[[6-(4-F!uorophenyl)pyrrolo[3,2-b]pyndin-1 -yl]methyl]-5- methyl-isoxazole trifluoroacetaie salt;

66 N-Cyclobutyl-2-[6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yi]acetamide trifluoroacetaie salt;

67 2-[6-(4-Fiuoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrrolidin-1 -yl-ethanone trifluoroacetaie salt;

68 1 -(Azetidin-1 -yl)-2-[3-bromo-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-bjpyridin-1 -yljeihanone;

69 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

70 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetic acid;

71 1 -(Azetidin-1 -yl)-2-[6-(2-fiuorophenyl)pyrrolo[3,2-b]pyridin-1 - yljeihanone;

72 1 -(Azetidin-1 -yl)-2-[6-(3-fluorophenyl)pyrroio[3,2-b]pyridin-1 - yljeihanone;

73 1 -(Azetidin-1 -yl)-2-[6-(p-tolyl)pyrrolo[3,2-b]pyridin-1 - yljeihanone;

74 1 -(Azetidin-1 -yl)-2-[6-(3-ethyiphenyl)pyrroio[3,2-bjpyridin-1 - yljeihanone; Example # Compound Name

75 N-Cyclopropyl-2-[6-(2-fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yljacetamide;

76 N-Cyclopropyi-2~[6-(3~fluorophenyl)pyrrolo[3,2-b]pyridin-1 ~ yljacetamide;

77 N-Cyclopropyl-2-[6-(p-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide;

78 2-(6-Pheny!pyrrolo[3,2-b]pyridin-1 -yl)-1 -pyrrolidin-1 -yl- ethanone;

79 2-[6-(2-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 - yl-eihanone;

80 2-[6-(4-Fiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 - yl-ethanone;

81 2-[6-(m-Tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 -yl- eihanone;

82 2-[6-(p-Tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 -yl- ethanone;

83 2-[6-(3-Ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yi]-1 -pyrroiidin-1 -yl- ethanone;

84 2-[6-(3-Fiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 - yl-ethanone;

85 1 -Morpholino-2-(6^henylpyrrolo[3,2-b]pyridin-1 -yl)ethanone;

86 2-[6-(2-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-1 -morphoiino- ethanone;

87 2-[6-(3-Fiuorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-1 -morphoiino- ethanone; Example # Compound Name

88 2-[8-(4-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-1 -morpholino- ethanone;

89 1 -Morpholino-2-[6-(m~toiyl)pyrrolo[3,2-b]pyridin-1 ~yi]eihanone;

90 1 -Morpholino-2-[6-(p-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

91 2-[6-(3-Ethylphenyl)pyrrolo[3,2-b]pyndin-1 -yl]-1 -morpholino- ethanone;

92 2-[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - yl]-N,N-dimethyl-acetamide;

93 2-[6-(3,4-Dif!uoropheny!)-3-fluoro-pyrro!o[3,2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide;

94 2-[3-Fluoro-6-(3,4,5-trifluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide;

95 2-[6-[3-(Difluoromethyl)phenyl]-3-fluoro-pyrrolo[3,2-b]pyrid in-1 - yl]-N,N-dimethyl-acetamide;

96 2-[3-Fluoro-6-(4-methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-

N,N-dirnethyl-aceiamide;

97 2-[6-(5-Ch!oro-2-thienyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 -yl]- N,N~dimethyl-acetamide;

98 2-[3-Fluoro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyi-acetamide;

99 N-Cyclopropy!-2-[6-[5-(irifluoromethyl)-3-pyridy!]pyrrolo[3, 2- b]pyridin-1 ~yi]acetamide;

100 N-Cyclopropyl-2-[6-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin -1 - yl]acetamide; Example # Compound Name

101 N-Cyclopropyi-2-[6-[4-fluoro-3-

(irifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 -y!]acetamide;

102 1 -(Azetidin~1 -yl)-2~[6~[5-(trifluoromethyl)~3-pyridyi]pyrrolo[3 _! 2~ b]pyridin-1 -yijethanone;

103 1 -(Azei!din-1 -yl)-2-[8-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin- 1 -yijethanone;

104 1 -(Azetidin-1 -yl)-2-[6-[4-f luoro-3-

(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin- -yijethanone;

105 2-[6-[4-fluoro-3-(trifluoromethyl)phenylJpyrrolo[3,2-b]pyrid in-1 - ylj-1 -pyrrolidin-1 -yl-ethanone;

106 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-[4-fluoro-3- (trifluoromethyl)phenylJpyrrolo[3,2-b]pyridin-1 -yijethanone;

107 2-[8-(3 _i 4-Difluorophenyl)pyrrolo[3,2-bJpyridin-1 -ylj-1 - morpholino-ethanone;

108 2-[6-[4-Fluoro-3-(trifluoromethyl)phenylJpyrrolo[3,2-bJpyrid in-1 - yl]-1 -morpholino-ethanone;

109 1 -(Azetidin-1 -yl)-2-[6-[2-(trifluoromethyl)-4-pyridylJpyrrolo[3,2- b]pyridin-1 -yijethanone;

1 10 N-Cyciopropyl-2-[6-[2-(trifluoromethyi)-4-pyridylJpyrrolo[3, 2- bjpyridin~1 -yijacetamide;

1 1 1 N-Cyclopropyl-2-[6-[6-(trifluoromethyl)-2-pyridyl]pyrrolo[3, 2- bjpyridin-1 -yljacetamide;

1 12 1 -(Azetidin-1 -yl)-2-[6-(6-methyl-3-pyridyl)pyrrolo[3,2-bJpyridin-

1 -yijethanone;

1 13 5-[1 -[2-(Azetidin-1 -yl)-2-oxo-ethyl]pyrrolo[3,2-b]pyridin-6- yl]pyridine-2-carbonitrile; Example # Compound Name

1 14O C 6-(3,4-Difluorophenyl)-1 -(pyrimidin-5-ylmethyl)pyrrolo[3,2- bjpyridine;

1 15 6-(3,4-Difiuorophenyi)-1 ~[(5-fluoropyrimidin~2~

yl)meihyl]pyrrolo[3,2-b]pyridine;

1 16 Cyclobutyl-[6-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin-1 - yljmethanone;

1 17 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[6-[6-(trifluoromethyl)-2- pyridyljpyrrolo[3,2-bjpyridin-1 -yljethanone;

1 -(Azetidin-1 -yl)-2-[6-(2,3,4-trifluorophenyl)pyrTolo[3,2- b]pyridin-1 -y!jeihanone;

1 19 2-Cyclopropyl-1 -[6-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin-1 - yljeihanone;

120 1 -Pyrrolidin-1 -yl-2-[6-(2,3,4-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone;

121 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[6-(3,5- difluorophenyi)pyrrolo[3,2~b]pyridin~1 -yljethanone;

122 2-[6-(3 _! 5-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-

1 -yl-ethanone;

123 1 -Pyrrolidin-1 -yl-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin~1 -yljethanone;

124 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone;

125 2-[6-(3 _! 5-Difiuorophenyl)pyrrolo[3,2-bjpyridin-1 -ylj-1 - morphoiino-ethanone;

126 1 -Morpholino-2-[6-(2,3,4-trifluorophenyl)pyrrolo[3,2-bjpyridi n-1 - yljethanone; Example # Compound Name

127 1 -Morpholino-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridi n-1 - yljethanone;

128 2-[6~(3 _! 4~Difluorophenyl)pyrroio[3,2-b]pyridin~1 -yl]-1 -(3- fluoroazeiidin-1 -yl)ethanone;

129 2-[6-(3 _i 5-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- f!uoroazeiidin-1 -y!)ethanone;

130 6-(4-Methyl-2-thienyl)-1 -(pyridazin-3-ylmethyl)pyrrolo[3,2- b]pyridine;

131 6-(3,4-Difluorophenyl)-1 -(pyridazin-3-ylmethyl)pyrrolo[3,2- bjpyridine;

132 2-[6-(4-!V1eihy!-2-thienyl)pyrrolo[3,2-b]pyridin-1 -y!]-1 - morpholino-ethanone;

133 1 -(Azei!din-1 -yl)-2-[8-(2,4-difluorophenyl)pyrrolo[3,2-b]pyridin- 1 -y!]ethanone;

134 1 -(Azetidin-1 -yl)-2-[6-(2,3-difluorophenyl)pyrro!o[3,2-b]pyrid!n- 1 ~yl]ethanone;

135 1 -(Azetidin-1 -yl)-2-[6-(2,5-difluorophenyl)pyrrolo[3,2-b]pyridin-

1 -yljethanone;

136 1 -Cyc!opropyl-2-[6-(3,4-dif!uoropheny!)-3-f!uoro-pyrro!o[3,2- b]pyridin~1 -yljethanone;

137 6-(4-Methyl-2-thienyl)-1 -[[5-(trifluoromethyl)-2- furyl]methyl]pyrrolo[3,2-b]pyridine;

138 6-(3,4-Difluorophenyl)-1 -[[5-(trifluoromeihyl)-2- furyl]methyl]pyrrolo[3,2-b]pyridine;

139 N,N-Dimethyl-2-[6-(4-methyl-2-thienyl)pyrrolo[3,2-b]pyridin- 1 - yl]acetamide; Example # Compound Name

140 1 -[6-(3,4-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-3,3- dimethyl-butan-2-one;

141 1 -[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-3,3- dimetbyl-buian-2-one;

142 1 -[6-(3,5-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-3,3- dimeihy!-butan-2-one;

143 3,3-Dimethyl-1 -[6-(4-methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 - yl]buian-2-one;

144 1 -[6-[3-(Difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]-3,3- dimethyl-butan-2-one;

145 1 -[6-(3-Ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-3,3-dimethyl- butan-2-one;

146 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - yl]-N,N-dimethyl-acetamide;

147 2-[3-Ch!oro-6-(3 _! 4-difluoropheny!)pyrro!o[3,2-b]pyrid!n-1 -yl]- Ν,Ν-dimethyl-acetamide;

148 2-[3-Chloro-6-(3 _! 5-difluorophenyl)pyrroio[3 _i 2-b]pyridin-1 -yl]- N,N-dimethyl-aceiamide;

149 2-[3-Chloro-6-(4-meihy!-2-thieny!)pyrrolo[3,2-b]pyridin-1 -y!]- N,N~dimethyl-acetamide;

150 2-[3-Chloro-6-[3-(difluoromethyl)phenyl]pyrrolo[3,2-b]pyridi n-1 - yl]-N,N-dimethyl-acetamide;

151 2-[3-Ch!oro-6-(3-ethylpheny!)pyrrolo[3,2-b]pyridin-1 -y!]-N,N- dimethyl-acetamide;

152 2-[3-Chioro-8-(3,4,5-irifiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]- N,N-dimethyl-aceiamide; Example # Compound Name

153 N-Cyclopropyl-2-[6-(4-methyl-2-thienyl)pyrrolo[3,2-b]pyridin -1 - yljacetamide trifluoroacetate salt;

154 N-Cyclopropyl-2~[6~(2,3~dimeihylphenyl)pyrroto[3,2-b]pyridin ~1 - yljacetamide trifluoroacetate salt;

155 N-Cyclopropyl-2-[6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide trifluoroacetate salt;

156 N-Cyclopropyi-2-[6-(3,4-dichlorophenyi)pyrrolo[3,2-b]pyridin -1 - yl]acetamide trifluoroacetate salt;

157 N-Cyciopropyl-2-[6-[2-metbyi-3-

(trifluoromethyl)phenyl]pyrrolo[3 _! 2-b]pyridin-1 -yl]acetamide trifluoroacetate salt;

158 N-Cyciopropyl-2-(6-phenylpyrrolo[3,2-b]pyridin-1 -yl)acetamide trifluoroacetate salt;

159 N-Cyclopropyl-2-[6-(4-fluoro-2,3-dimethyl-phenyl)pyrrolo[3,2 - b]pyridin-1 -yl]acetamide trifluoroacetate salt;

160 N-Cyciopropyi-2-[6-(o-tolyi)pyrrolo[3,2-b]pyridin-1 -yi]acetamide;

161 N-Cyciopropyi-2-[6-(4-fiuoro-2-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yi]acetamide trifluoroacetate salt;

162 1 -(Azetidin-1 -yl)-2-[6-(o-tolyl)pyrrolo[3,2-b]pyridin-1 - yljethanone trifluoroacetate salt;

163 1 -(Azetidin-1 -yl)-2-[6-(4-fiuoro-2-metbyi-phenyi)pyrrolo[3,2- b]pyridin-1 -yljethanone trifluoroacetate salt;

164 1 -(Azetidin-1 -yl)-2-[6-(4-fluoro-2, 3-dimethyi-phenyl)pyrrolo[3, 2- b]pyridin-1 -yljethanone trifluoroacetate salt;

165 1 -(Azetidin-1 -yl)-2-[6-(2,3-dimethylphenyl)pyrrolo[3,2-b]pyridin-

1 -yljethanone trifluoroacetate salt; Example # Compound Name

166 1 -(Azetidin-1 -yl)-2-[6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -y!]eihanone trif!uoroaceiate salt;

167 1 -(Azetidin-1 -yl)-2-[6-[2-methyl-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]ethanone trifiuoroacetate salt;

168 N-Cyclopropyl-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yljacetamide;

169 1 -(Azetidin-1 -yl)-2-[6-(4-fluoro-3-methyi-phenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]ethanone trifiuoroacetate salt;

170 1 -Butyl-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridine

trifiuoroacetate salt;

171 6-(4-Fluoro-3-methyl-phenyl)-1 -isopenty!-pyrrolo[3,2-b]pyridine trifiuoroacetate salt;

172 6-(4-Fluoro-3-methyl-phenyl)-1 -(3-pyridylmethyl)pyrrolo[3,2- bjpyridine trifiuoroacetate salt;

173 1 -(Cyclobutylmethyi)-6-(4-fluoro-3-methyi-phenyl)pyrrolo[3,2- bjpyridine trifiuoroacetate salt;

174 1 -(Cyclopropylmethyl)-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2 - b]pyridine trifiuoroacetate salt;

175 2-[6-(4-Fluoro-3-methyl-phenyl)pyrroio[3,2-b]pyridin-1 -yl]-N,IM- dimethyi-acetamide trifiuoroacetate salt;

176 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - ylj-N-cyclopropyi-acetamide trifiuoroacetate salt;

177 6-(4-Fluoro-3-methyl-phenyl)-1 -(2-pyridylmethyl)pyrrolo[3,2- bjpyridine trifiuoroacetate salt;

178 (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 -(tefrahydrofuran-3- ylmethyi)pyrrolo[3,2-b]pyridine trifiuoroacetate salt; Example # Compound Name

179 6-(4-Fluoro-3-methyl-phenyl)-1 -(4-pyridylmethyl)pyrrolo[3,2- bjpyridine trifluoroacetate salt;

180 (R/S)~6-(4~Fluoro~3-methyl~phenyl)-1 ~(oxiran~2- ylmethyl)pyrrolo[3,2-b]pyridine trifluoroacetate salt;

181 6-(4-Fluoro-3-methyl-phenyl)-1 -(2-pyrazol-1 -ylethyl)pyrrolo[3,2- bjpyridine trifluoroacetate salt;

182 1 -(Azetidin-1 -yl)-2-[6-(5-chloro-2-thienyl)-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yl]ethanone;

183 6-(4-Fluoro-3-methyl-phenyl)-1 -(pyrimidin-2- ylmethyl)pyrrolo[3,2-b]pyridine trifluoroacetate salt;

184 (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 -(oxetan-2- ylmethyl)pyrrolo[3,2-b]pyridine trifluoroacetate salt;

185 1 -(3,3-Difluoroazetidin-1 -yl)-2-[3-fluoro-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

186 1 -Cyclopropyi-2-[6-(4-fiuoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 ~yl]ethanone trifluoroacetate salt;

187 1 -[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-3- methyl-butan-2-one trifluoroacetate salt;

188 2-[6-(4-Fluoro-3-methyl-phenyl)pyrroio[3,2-b]pyridin-1 -yl]-1 -(4- hydroxy~1 -piperidyl)ethanone trifluoroacetate salt;

189 (R/S)-1 -(3-Azabicycio[3.1 .0]hexan-3-yl)-2-[6-(4-fluoro-3-methyl- phenyi)pyrrolo[3,2-b]pyridin-1 -yljethanone trifluoroacetate salt;

190 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(4- methoxy-1 ~piperidyl)ethanone trifluoroacetate salt;

191 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(4- fluoro-1 -piperidyl)ethanone trifluoroacetate salt; Example # Compound Name

192 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -[4-

(fluoromethyl)-1 -piperidyl]ethanone trif!uoroacetate salt;

193 2-[8~(4-Fluoro-3~methyl-phenyl)pyrrolo[3,2-b]pyridin~1 -yl]-1 -(1 - piperidyl)ethanone trifluoroacetate salt;

194 (R/S)-2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]- i -(2-methylmorpholin-4-yl)ethanone trifluoroacetate salt;

195 (R/S)-2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]- 1 -[3-(trifluoromethyl)-1 -piperidyljeihanone trifluoroacetate salt;

196 (R/S)-1 -(2-Ethylpyrrolidin-1 -yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3 _! 2-b]pyridin-1 -yijethanone trifluoroacetate salt;

197 1 -(2,2-Dimethylmorpholin-4-yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone trifluoroacetate salt;

198 (R/S)-2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-

1 -(3-methoxypyrrolidin-1 -yi)ethanone trifluoroacetate salt;

199 (R/S)-2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-

1 ~(3~fiuoro-1 ~piperidyi)ethanone trifluoroacetate salt;

200 1 -(2,2-Dimethylpyrrolidin-1 -yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone trifluoroacetate salt;

201 2-[6-(4-Fluoro-3-methyl-phenyi)pyrroio[3,2-bjpyridin-1 -yl]-1 - [(3R)~3-fluoropyrroiidin-1 -yijethanone trifluoroacetate salt;

202 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3-hydroxy-3- methyi-azetidin-1 -yl)ethanone;

203 2-[6-(4-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -ylj-1 -[3-hydroxy-3- (trifiuoromethyi)azetidin-l -yijethanone;

204 1 ~(3-Fluoroazefidin-1 -yl)-2-[6-(4-fluorophenyi)pyrrolo[3,2- b]pyridin-1 -yijethanone; Example # Compound Name

205 N-Cyclopropyl-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]- N-methyl-acetamide;

206 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]~1 -[3- (hydroxymethyl)azetidin-l -yljethanone;

207 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- meihoxyazeiidin-1 -yl)ethanone;

208 1 -(5-Azaspiro[2.3]hexan-5-yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone trifluoroaceiate salt;

209 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(4- hydroxy-4-meihyl-1 -piperidyl)ethanone trifluoroacetate salt;

210 (R/S)-2-[6-(4-Fluoro-3-meihyl-phenyl)pyrrolo[3,2-b]pyridin-1 -ylj- 1 -(3-methylmorpholin-4-yl)ethanone trifluoroacetate salt;

21 1 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- hydroxyazetidin-1 -yl)ethanone;

212 1 -[2-[6-(4-Fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 - yl]acetyl]azetidine~3-carbonitrile;

213 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone;

214 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- methylazetidin-1 -yljethanone;

215 1 -(3,3-Dimethylazetidin-1 -yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone;

216 1 -[2-[6-(4-Fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 - yl]acetyl]pyrrolidin-3~one trifluoroacetate salt;

217 1 -(3,3-Difluoropyrrolidin-1 -yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone; Example # Compound Name

218 (R/S)-2-[6-(4-Fluorophenyi)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- hydroxypyrrolidin-1 -yl)ethanone;

219 1 -Cyclopropyi-2~[6~(m-iolyl)pyrroto[3,2-b]pyridin~1 -yl]ethanone;

1 -Cyclopropyl-2-(6-phenylpyrrolo[3,2-b]pyridin-1 -yl)ethanone;

221 1 -Cyclopropy!-2-[6-(3-fluorophenyl)pyrro!o[3,2-b]pyridin-1 - yl]ethanone;

222 1 -Cyclopropyl-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yljethanone;

223 1 -[6-(4-Fluoro-2,3-dimethyl-phenyl)pyrrolo[3,2-b]pyndin-1 -yl]-3- methyl-butan-2-one;

224 1 - [6-(3-Ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-3-methyl-butan-

2- one;

1 -[6-(2,3-Dimethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-3-methyl- buian-2~one;

226 2-[8-(4-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-1 -phenyl- ethanone;

227 1 -(4-Fluorophenyl)-2-[6-(4-f!uoropheny!)pyrro!o[3,2-b]pyridin -1 - yljethanone;

228 (R/S)-6-(4-Fluorophenyl)-1 -(tetrahydropyran-2- y!methyl)pyrrolo[3,2-b]pyridine trifluoroacetate salt;

223 2-[6-(4-Fluoropheny!)pyrro!o[3,2-b]pyridin-1 -yl]-N-isopropy!- aceiamide;

230 2-[8-(4-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-N-propyl- acetamide; Example # Compound Name

231 (R/S)-2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyriclin-1 -yl]-N-(2,2,2- irifluoro-1 -metbyl-ethyl)aceiarnide;

232 2-[8~(4-Fluorophenyl)pyrrolo[3 _! 2-b]pyridin~1 -y!]~N~(1 - methylcyclopropyl)acetamide;

233 N-(2-Fluoroeihyl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin -1 - yljacetamide;

234 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N-isobutyl- acetamide;

235 5-[[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 - yl]methyl]-3-methyl-1 ,2,4-oxadiazole;

236 6-(4-Fluoro-3-meihyl-phenyl)-1 -[(1 -metbylpyrazol-4- yl)meihyl]pyrrolo[3,2-b]pyridine;

237 N-(Cyclopropylmethyl)-2-[6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]acetamide;

238 6-(4-Fluoro-3-methyl-phenyl)-1 -[(1 -methyltriazol-4- yl)methyl]pyrrolo[3,2~b]pyridine;

239 5-[[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyrid in- 1 -yl]methyl]-3-methyl-1 ,2,4-oxadiazole;

240 3-Chloro-6-(4-fluoro-3-meihyl-phenyl)-1 -[(1 -meihylpyrazol-4- yl)methyl]pyrrolo[3,2-b]pyridine;

241 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - y!j-1 -cyclobutyi-ethanone;

242 1 -Cyclobutyl-2-[6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yljeihanone;

243 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[5-(trifluoromethyl)-3- pyridyl]pyrrolo[3,2-b]pyridin-1 -yljeihanone trifluoroacetate salt; Example # Compound Name

244 2-[3-Chloro-6-[5-(trifluoromethyl)-3-pyridyl]pyrrolo[3,2-b]p yridin- 1 -yl]-N-cyclopropyl-acetamide trif!uoroaceiate salt;

245 1 -(Azetidin~1 -yl)-2~[3~chloro-6~[6~(trifluoromeihyl)-2~

pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

246 2-[3-Chloro-6-[6-(trifluoromethyl)-2-pyridyl]pyrrolo[3,2-b]p yridin-

1 -yl]-N-cyclopropyl-acetamide;

247 2-[3-Chloro-6-[6-(trifluoromethyl)-2-pyridyl]pyrrolo[3,2-b]p yrldin- 1 -yl]-1 -(3-fluoroazetidin-1 -yl)eihanone;

248 N-Cyclopropyl-2-[6-(3,4,5-irifluorophenyl)pyrrolo[3,2-b]pyri din- 1 -yl]acetamide;

249 N-Cyclopropyl-2-[6-(2,3,4-irifluorophenyl)pyrrolo[3,2-b]pyrl din- 1 -yl]acetamide;

250 N-Cyclopropyl-2-[6-[3-(difluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yl]acetamide;

251 N-Benzy!-2-[6-(4-fluorophenyl)pyrrolo[3 _! 2-b]pyrldin-1 - yljacetamide;

2-[[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 - yljmethyljoxazole;

2-[6-(4-Fluorophenyl)pyrrolo[3 _! 2-b]pyridln-1 -y!]-N-(2- hydroxyethyl)acetamide;

254 2-[6-(4-Fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -yl]-N-(2- meihoxyethyl)acetamide;

255 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[6-[2-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]ethanone trifluoroacetate salt;

256 1 -(3,3-Difluoroazetidln-1 -yl)-2-[6-(3-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]ethanone trifluoroacetate salt; Example # Compound Name

257 1 -(3,3-Difluoroazetidin-1 -yl)-2-(6-phenylpyrrolo[3,2-b]pyridin-1 - yljethanone trifiuoroacetaie salt;

258 1 -(3,3-Difluoroazetidin-1 ~yl)~2-[6-(3-ethylphenyl)pyrrolo[3,2- b]pyridin-1 -yl]ethanone trifluoroacetate salt;

259 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-bJpyridin-1 -yljethanone trifluoroacetate salt;

260 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yljethanone trifluoroacetate salt;

261 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(4-fluoro-2-methyl- phenyi)pyrrolo[3 _! 2-bJpyridin-1 -yljethanone trifluoroacetate salt;

262 1 -(3-Fiuoroazefidin-1 -yl)-2-[6-[4-fluoro-3- (trifluoromethyl)phenylJpyrrolo[3,2-b]pyridin-1 -yljethanone trifluoroacetate salt;

263 1 -(3-Fiuoroazetidin-1 -yl)-2-[6-(3-fluorophenyl)pyrrolo[3,2- bjpyridin-1 -yljethanone trifluoroacetate salt;

264 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(4-fluoro-2-methyl- phenyi)pyrrolo[3 _! 2-bJpyridin-1 -yljethanone trifluoroacetate salt;

265 1 -(3-Fluoroazefidin-1 -yl)-2-[6-[3-

(trifluoromethyl)phenylJpyrrolo[3,2-b]pyridin-1 -yljethanone trifluoroacetate salt;

266 1 -(3-Fluoroazefidin-1 -yl)-2-[6-(m-tolyl)pyrroio[3,2-bJpyridin-1 - yljethanone trifluoroacetate salt;

267 1 -(3-Fiuoroazetidin-1 -yl)-2-[6-[2-fluoro-3-

{trifiuoromethyi)phenylJpyrrolo[3,2-bJpyridin-1 -yljethanone trifluoroacetate salt;

268 2-[6-(3-Ethylphenyi)pyrrolo[3,2-bJpyridin-1 -yij-1 -(3- fluoroazetidin~1 -yljethanone trifluoroacetate salt;

269 1 -(3,3-Difluoroazetid!n-1 -yl)-2-[6-(m-tolyl)pyrroio[3,2-bJpyridin- 1 -yljethanone; Example # Compound Name

270 1 -(3-Fluoroazeiidin-1 -yl)-2-(8-phenylpyrrolo[3,2-b]pyridin-1 - yljeihanone;

271 1 -(3,3-Difiuoroazetidiri-1 ~yl)~2-[6-(2,4-difiuoro~3-methyl~phenyl)- 3-fluoro-pyrrolo[3,2-bjpyridin-1 -yljeihanone;

272 (R/S)-1 -[6-(3,5-Difluoropbenyl)pyrrolo[3,2-b]pyridin-1 -ylj-3- methyl-butan-2-ol;

273 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- hydroxyazeiidin-1 -yl)etbanone;

274 (R/S)-1 -Cyclopropyl-2-[6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- bjpyridin-1 -y!jeihano!;

275 (R/S)-2-Cyclopropy!-1 -[6-(4-fluoro-3-meihy!-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]propan-2-ol trifluoroacetate salt;

276 1 -Cyclopropyl-2-[6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N-methoxy-ethanimine;

277 1 -(3-F!uoroazetidin-1 -yl)-2-[6-(2-thienyl)pyrrolo[3,2-b]pyridin-1 - yljeihanone;

278 1 -Pyrrolidin-1 -yl-2-[6-(2-thienyl)pyrrolo[3,2-b]pyridin-1 - yljeihanone;

279 1 -(3,3-Difluoroazeiidin-1 -yl)-2-[6-(5-methyl-2- thienyl)pyrrolo[3,2~bjpyridin-1 -yljeihanone;

280 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(5-methyl-2-thienyl)pyrrolo[3,2- bjpyridin-1 -yljeihanone;

281 2-[6-(5-Ethyl-2-ihienyl)pyrrolo[3,2-bjpyridin-1 -ylj-1 -(3- fluoroazeiidin~1 -yljeihanone;

282 2-[8-(5-Eihyl-2-ihienyl)pyrrolo[3,2-bjpyridin-1 -yl]-1 -pyrrolidin-1 - yl-eihanone; Example # Compound Name

283 2-[6-(5-Methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-

1 -yl-ethanone;

284 1 -(3,3-Difiuoroazetidin-1 ~yl)~2-[6-(5-ethyi-2~thienyl)pyrrolo[3,2~ b]pyridin-1 -yijethanone;

285 2-[8-(4-Ghloro-2-ihienyl)pyrroio[3,2-bjpyridin-1 -yl]-1 -(3- f!uoroazeiidin-1 -y!)ethanone;

286 1 -Cyclopropy!-2-[6-(4-fluoro-3-meihy!-phenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone o ime trifluoroacetate salt;

287 2-[8-(5-Chloro-2-thienyl)pyrrolo[3 _i 2-b]pyridin-1 -yl]-1 -pyrrolidin- 1 -yl-ethanone;

288 2-[6-(4-Ch!oro-2-thieny!)pyrrolo[3 _! 2-b]pyridin-1 -yl]-1 -pyrrolidin- 1 -yl-ethanone;

289 (R/S)-1 -(2-Cyclopropyl-2-fluoro-ethyl)-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridine;

290 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- methoxyazetidin~1 -yijethanone;

291 6-(4-Fluoro-3-methyl-phenyl)-1 -(2-methoxyethyl)pyrrolo[3,2- b]pyridine trifluoroacetate salt;

202 1 -Cyclobutyl-2-[6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yijethanone;

293 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -[(3R)-3- fluoropyrrolidin-1 -yijethanone trifluoroacetate salt;

294 2-[6-(4-Fluorophenyl)pyrroio[3,2-bjpyridin-1 -ylj-1 -[(3S)-3- fluoropyrrolidin-1 -yijethanone trifluoroacetate salt;

295 1 - [6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]butan-

2- one trifluoroacetate salt; Example # Compound Name

296 N-Ethyl-2-[6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin -1 - ylj-N-metbyi-acetamide;

297 N,N~Diethyl~2-[6~(4-fluoro-3~meihyl-phenyl)pyrroio[3,2- b]pyridin-1 -yl]acetamide;

298 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[3-

(trif!uoromeiby!)pbenyl]pyrro!o[3,2-b]pyridin-1 -yl]ethanone;

299 2-[3-Chloro-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -cyclopropyl- ethanone;

300 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 -cyclopropyl- ethanone;

301 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3, 4, 5-trifluorophenyl)pyrrolo[3, 2- b]pyridin-1 -yijethanone;

302 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone;

303 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3,5-dimethylphenyi)pyrrolo[3, 2- b]pyridin-1 -yijethanone;

304 2-[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - yl]-1 -morpholino-ethanone;

305 2-[3-F!uoro-6-(4-f!uoropheny!)pyrrolo[3,2-b]pyridin-1 -yl]-1 - morpholino-ethanone;

306 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone;

307 1 -(3-F!uoroazetidin-1 -yl)-2-[3-fluoro-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone;

308 1 ~(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(4- fluorophenyl)pyrrolo[3,2-bjpyridin-1 -yijethanone; Example # Compound Name

309 1 ~(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(4-methyl-2- ihieny!)pyrrolo[3,2-bjpyridin-1 -yljethanone;

310 2-[8~[3-(Difluoromethyl)phenyl]-3~fluoro~pyrroto[3,2-b]pyrid in~1 - yl]-1 -(3-fluoroazetidin-1 -yl)ethanone;

31 1 2-[8-(3 _i 4-Difiuorophenyl)-3-fluoro-pyrrolo[3 _i 2-b]pyridin-1 -yl]-1 - (3-fluoroazetidin-1 -yl)eihanone;

312 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(2,3,4-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]ethanone;

313 2-[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - yl]-1 -pyrrolidin-1 -yl-eihanone;

314 2-[3-F!uoro-6-(4-f!uoropheny!)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrrolidin-1 -yl-ethanone;

315 2-[3-Fluoro-6-(3,4,5-trifluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -yl]-1 - pyrrolidin-1 -y!-ethanone;

316 1 -Cyclopropy!-2-[3-f!uoro-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

317 1 -Cyclopropyl-2-[3-fluoro-6-(4-methyl-2-ihienyl)pyrroio[3 _! 2- b]pyridin-1 -yljethanone;

318 2-[6-(5-Ch!oro-2-thienyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 -yl]-1 - cyclopropyi-ethanone;

319 1 -Cyclopropyl-2-[3-fluoro-6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone;

320 1 -Cyclopropy!-2-[3-f!uoro-6-(3,4,5-trifluorophenyl)pyrro!o[3, 2- b]pyridin-1 -yljethanone;

321 1 -Cyclopropyl-2-[6-[3-(difluoromethyl)phenylj-3-fluoro- pyrrolo[3,2-bjpyridin-1 -yljethanone; Example # Compound Name

322 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(4-methyi-2-ihienyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone;

323 1 -(Azetidin~1 -yl)-2~[8~[3-(difiuoromeihyi)phenyl]-3~fiuoro~

pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

324 1 -[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin -1 - y!]-3-meihy!-butan-2-one;

325 1 -[6-(3-Eihy!phenyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 -yl]-3- methyl-butan-2-one;

326 1 -[6-(3,4-Difluorophenyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 -yl]-3- methyl-butan-2-one;

327 1 -[3-F!uoro-6-(3-f!uoropheny!)pyrrolo[3,2-b]pyridin-1 -yl]-3- methyl-butari-2-one;

328 1 -[3-Fluoro-6-[3-(irifiuoromethyl)phenyl]pyrrolo[3,2-b]pyridi n-1 - y!]-3-meihy!-butan-2-one;

329 1 -[3-Fluoro-6-(m-io!yl)pyrro!o[3,2-b]pyridin-1 -yl]-3-methyl- buian-2~one;

330 6-(4-Fluoro-3-methyl-phenyl)-1 - (methylsulfanylmethyl)pyrrolo[3,2-b]pyridine;

331 (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 - (methylsulfinylmethyl)pyrrolo[3,2-b]pyridine;

332 6-(4-Fluoro-3-methyl-phenyl)-1 - (methylsulfonylmethyl)pyrrolo[3,2-b]pyridine;

333 1 -[3-Fluoro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]butan-2- one;

334 1 -[3-Fluoro-6-(3,4,5-trifluorophenyl)pyrrolo[3,2-b]pyridin-1 - yl]buian-2-one; Example # Compound Name

335 1 -[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin -1 - yl]buian-2-one;

336 1 -[6~(3 _! 4~Difluorophenyl)~3-fluoro~pyrrolo[3 _! 2-b]pyridin-1 - yl]butan-2-one;

337 1 -[6-[3-(Difluoromethyl)phenyl]-3-fluoro-pyrrolo[3,2-b]pyridi n-1 - y!]butan-2-one;

338 1 -[6-(5-Chloro-2-ihienyl)-3-f!uoro-pyrrolo[3 _! 2-b]pyridin-1 - yl]buian-2-one;

339 1 -[3-Fluoro-6-(4-methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 - yl]buian-2-one;

340 4-[6-(4-F!uorophenyl)pyrrolo[3,2-b]pyridin-1 -y!]butan-2-one;

341 1 -[3-Fluoro-6-(4-fluorophenyi)pyrrolo[3,2-b]pyridin-1 -yl]-3- meihy!-buian-2-one;

342 1 -[6-[3-(Difluoromethyl)phenyl]-3-fluoro-pyrrolo[3,2-b]pyridi ri-1 - yl]~3-methyl~butan-2~one;

343 1 -[3-Fluoro-6-(4-methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-3- methyl-butan-2-one;

344 l-P-Fluoro-e^S^.S-irifluorophenyljpyrrolop^-bjpyridin-l -ylj-S- methyl-butan-2-one;

345 1 -[6-(5-Chloro-2-thienyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 -yl]-3- meihyi-butan-2-one;

346 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - morpholino-ethanone;

347 1 -(3-Fluoroazeiidin-1 -yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; Example # Compound Name

348 N-Cyclopropyi-2-[6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -y!]acetamide;

349 1 -(Azeiidin-l -yl)-2~[6~(4~fluoro-3~meihyi-phenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone;

350 N-Cyclopropyl-2-[6-(3,5-difluorophenyl)pyrrolo[3,2-b]pyridin -1 - y!jacetamide trifiuoroaceiate salt;

351 N-Cyclopropy!-2-[6-[3-(irifluoromethyl)pheny!]pyrrolo[3,2- b]pyridin-1 -yl]acetamide trifiuoroaceiate salt;

352 N-Cyclopropyi-2-[6-[2-fluoro-3-

(trifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 -y!]acetamide trifiuoroaceiate salt;

353 1 -(Azetidin-1 -yl)-2-[6-(4-f!uoropheny!)pyrroio[3,2-b]pyridin-1 - yijethanone;

354 1 -(Azetidin-1 -yl)-2-(6-phenyipyrrolo[3,2-b]pyridin-1 - yl)ethanone;

355 1 -(Azei!din-1 -yl)-2-[6-(3,5-difiuorophenyl)pyrrolo[3,2-b]pyridin- 1 -yijethanone;

356 1 -(Azetidin-1 -yl)-2-[6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yijethanone trifiuoroaceiate salt;

357 1 -(Azetidin-1 -yl)-2-[6-(3,4-dich!orophenyi)pyrro!o[3,2-b]pyridin- 1 -yijethanone trifiuoroaceiate salt;

358 1 -(Azetidin-1 -yl)-2-[6-[2-fluoro-3-

(trifluoromethyl)phenyijpyrrolo[3,2-bjpyridin-1 -yijethanone trifiuoroaceiate salt;

359 1 -(Azetidin-1 -yl)-2-[6-(4-methyl-2-thienyl)pyrrolo[3,2-b]pyridin-

1 -yijethanone trifiuoroaceiate salt;

360 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(4-fluoro-3-methyl- phenyi)pyrrolo[3,2-bjpyridin-1 -yijethanone; Example # Compound Name

361 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(3,4- difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

362 1 -(Azetidin~1 -yl)-2~[6~[6-(trifluoromethyl)~2-pyridyi]pyrrolo[3 _! 2~ b]pyridin-1 -yijethanone;

363 1 -(Azetidin-1 -yl)-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone;

364 1 -[6-(3 _! 5-Difluorophenyl)pyrro!o[3,2-b]pyridin-1 -yl]-3-methyl- buian-2-one;

365 1 -Cyclobutyl-2-[6-(4-fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 - yijethanone;

366 N-Cyclopropyl-2-[6-(3-ethylphenyl)pyrrolo[3,2-b]pyridin-1 - yljacetamide;

367 2-[6-(3 _i 4-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin- 1 -yl-ethanone;

368 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[6-(4-methyl-2- thienyl)pyrroto[3,2-b]pyridin~1 -yijethanone;

369 2-[6-(4-Methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-

1 -yl-ethanone;

370 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(4-methyl-2-thienyl)pyrrolo[3,2- bjpyridin~1 -yijethanone;

371 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2- bjpyridin-1 -yijethanone;

372 2-[6-(5-Chloro-2-thienyl)pyrrolo[3,2-bjpyridin-1 -ylj-1 -(3- fluoroazetidin~1 -yijethanone;

373 1 -(Azetidin-1 -yl)-2-[6-(5-chloro-2-thienyl)pyrrolo[3,2-b]pyridin-1 - yijethanone; Example # Compound Name

374 2-[3-Chioro-6-(2,3,4-irifiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]- 1 -(3-fluoroazetidin-1 -yl)eihanone;

375 N,N~Dimeihyl-2~[6~(3,4,5~trifiuorophenyi)pyrrolo[3,2~b]pyrid in~1 - yljacetamide;

376 2-[6-(3 _i 5-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N _i N- dimethyl-acetamide;

377 2-[6-[3-(Difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyi-aeetamide;

378 2-[6-(5-Chloro-2-thienyl)pyrroio[3 _i 2-b]pyridin-1 -yl]-N _! N- dimethyl-acetamide;

379 2-[6-(3,4-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

380 1 -(Azeiidin-1 -yl)-2-[6-(5-methyl-2 -tbienyl)pyrrolo[3,2-b]pyridin- 1 -y!]ethanone;

381 1 -(Azeiidin-1 -yl)-2-[3-chloro-6-(5-ch!oro-2-thienyl)pyrrolo[3, 2- b]pyridin-1 -yijeihanone;

382 1 -(Azetidin-1 -yl)-2-[6-(3,4-difluorophenyl)-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yijeihanone;

383 1 -(Azetidin-1 -y!)-2-[3-fiuoro-6-(3 _! 4,5-trifiuorophenyl)pyrroio[3 _! 2- b]pyridin~1 -yijeihanone;

384 2-[3-Cbloro-6-(4-fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -yl]-1 - cyclopropyi-ethanone;

385 1 -(Azeiidin-1 -yl)-2-[6-(3-ihienyl)pyrrolo[3,2-b]pyridin-1 - yijeihanone irifiuoroacetate salt;

386 N,N-Dimethyl-2-[6-(5-methyl-2-thienyl)pyrrolo[3,2-b]pyridin- 1 - yljacetamide irifiuoroacetate salt; Example # Compound Name

387 2-[3-Fluoro-6-(2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

388 2-[6-(5-Ethyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-N _! N-dimethyl- acetamide irifluoroaceiate salt;

389 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(2-thienyl)pyrrolo[3 _i 2-b]pyridin-1 - y!jeihanone irifluoroaceiate salt;

390 2-[3-Fluoro-6-(5-meihyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yi]- N,N-dimethyl-acetamide;

391 2-[8-(4-Chloro-2-thienyl)pyrroio[3 _i 2-b]pyridin-1 -yl]-N _! N- dimethyl-aceiamide trifluoroacetaie salt;

332 1 -(Azetidin-1 -yl)-2-[6-(5-ethyi-2-ihienyl)pyrrolo[3 _! 2-b]pyridin-1 - yljeihanone irifluoroaceiate salt;

393 2-[6-(5-Ethyl-2-thienyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

394 1 -(Azetidin-1 -yl)-2-[6-(4-chloro-2-thienyl)pyrrolo[3,2-b]pyridin-1 - yljeihanone irifluoroaceiate salt;

395 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(2-thienyl)pyrrolo[3,2- b]pyridin-1 -yljeihanone irifluoroaceiate salt;

396 2-[6-(4-Chloro-2-ihienyl)-3-fluoro-pyrrolo[3,2-bjpyridin-1 -yl]- N,N~dimeihyl-aceiamide;

397 1 -(Azei!din-1 -yl)-2-[6-(4-chloro-2-thienyi)-3-fluoro-pyrroio[3,2- bjpyridin-1 -yljeihanone irifluoroaceiate salt;

398 2-[6-(5-Eihyl-2-ihienyl)-3-fluoro-pyrrolo[3,2-bjpyridin-1 -ylj-1 -(3- fluoroazeiidin~1 -yljeihanone irifluoroaceiate salt;

399 1 -(Azetidin-1 -yl)-2-[6-(2-thienyl)pyrrolo[3,2-b]pyridin-1 - yljeihanone; Example # Compound Name

400 N,N-Dimethyl-2-[6-(2-thienyl)pyrrolo[3,2-b]pyridin-1 - yljacetamide;

401 1 -(Azetidin~1 -yl)-2~[8~(5-ethyl~2-ihienyl)~3-fluoro~pyrrolo[3,2- b]pyridin-1 -yljethanone;

402 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(5-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yljethanone trifluoroacetate salt;

403 1 -(Azetidin-1 -yl)-2-[6-(3-chloro-2-thieny!)pyrrolo[3,2-b]pyridin-1 - yl]ethanone;

404 1 -(Azetidin-1 -yl)-2-[6-(2-methylthiazol-5-yl)pyrrolo[3,2-b]pyridin- 1 -yljethanone;

405 1 -(Azetidin-1 -yl)-2-(6-thiazoi-5-ylpyrrolo[3 _! 2-b]pyridin-1 - yl)ethanone;

406 1 -(Azetidin-1 -yl)-2-[6-(6-fluoro-3-pyridyl)pyrrolo[3,2-b]pyridin-1 - yljethanone;

407 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(4-methyl-2-thienyl)pyrrolo[3, 2- bjpyridin-1 -yljethanone;

408 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(5-ethyl-2-thienyl)pyrroio[3, 2- b]pyridin-1 -yljethanone;

409 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(2-thienyi)pyrrolo[3,2-bjpyridin-1 - yljethanone;

410 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(5-methyl-2-thienyi)pyrrolo[3, 2- bjpyridin-1 -yljethanone;

41 1 2-[6-(4-Fluorophenyl)pyrroio[3,2-bjpyridin-1 -yij-N-methyl-N- (2,2,2-trifluoroethyl)acetamide;

412 2-[3-Chloro-6-(5-methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -

(3-fiuoroazetidin-1 -yl)ethanone; Example # Compound Name

413 2-[3-Chloro-6-(5-chloro-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -

(3-f!uoroazetidin-1 -y!)ethanone;

414 2-[3~Chloro-6~(4-chloro-2~thienyl)pyrrolo[3,2~b]pyridin-1 ~yl]- N,N-dimethyl-acetamide;

415 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N- meihy!-N-(2,2,2-trif!uoroethy!)acetamide;

416 2-[3-Ch!oro-6-(4-methyl-2-ihienyl)pyrro!o[3,2-b]pyridin-1 -yl]-1 - (3-fluoroazetidin-1 -yl)ethanone;

417 2-[3-Chloro-6-(2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- fluoroazetidin-1 -yl)ethanone;

418 2-[3-Chloro-6-(4-chloro-2-ihienyl)pyrro!o[3,2-b]pyrid!n-1 -yl]-1 - (3-fluoroazeiidin-1 -yl)eihanone;

419 N-Eihyl-2-[8-(4-fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-N- methyl-acetamide;

420 2-[3-Ch!oro-6-(2-ihienyl)pyrro!o[3,2-b]pyrid!n-1 -yl]-N _! N- dimethyl-acetamide;

421 2-[3-Chloro-6-(5-ethyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyi-acelamide;

422 1 -(Azetidin-1 -y!)-2-[3-ch!oro-6-(4-chloro-2-ihieny!)pyrro!o[3,2- b]pyridin~1 -yljethanone;

423 2-[3-Chloro-6-(5-chloro-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide;

424 2-[3-Ch!oro-6-(5-ethyl-2-thieny!)pyrro!o[3,2-b]pyridin-1 -yl]-1 -(3- fluoroazetidin~1 -yl)ethanone;

425 2-[6-[2-Fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyrid in-1 - yl]-N,N-dimethyl-acetamide; Example # Compound Name

426 2-[6-(5-Chloro-4-methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-

N,N~dimethyl-aceiamide;

427 2-[6~(2,5~Dimethyl~3-ihienyl)pyrroio[3,2-b]pyridin~1 -yl]~N _! N~ dimethyl-acetamide;

428 N.N-Dimeihyl^-p^^^-trimethyi-S-ihienyiipyrrolop^- bjpyridin-1 -yljaceiamide;

429 2-[6-(3-Chlorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl- acetamide;

430 2-[6-(4-Fluorophenyl)pyrroio[3 _i 2-b]pyridin-1 -yl]-N,N-dimethyl- aceiamide;

431 2-[6-(2-F!uorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -y!]-N,N-dimeihy!- acetamide;

432 2-[6-(2-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

433 N,N-Dimethyl-2-(6-phenylpyrrolo[3,2-b]pyridin-1 -yl)acetamide;

434 N,N-Dimethyl-2-[6-(m-tolyl)pyrroio[3,2-b]pyridin-1 -yl]acetamide;

435 N,N-Dimethyl-2-[6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin~1 -yl]aceiamide;

436 2-[6-[4-Fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyrid in-1 - yl]-N,N-dimethyl-acetamide;

437 N,N-Dimethyl-2-[6-(2,3,4-trifluorophenyl)pyrrolo[3,2-b]pyrid in-1 - yljacetamide;

438 N,N-Dimethyl-2-[6-[5-(trifluoromethyl)-2-thienyl]pyrrolo[3,2 - b]pyridin-1 -yi]acetamide; Example # Compound Name

439 2-[8-(5-Chloro-3-thienyl)pyrroio[3 _i 2-b]pyridin-1 -yl]-N _! N- dimethyl-acetamide;

440 2-[8~(2,5~Dichloro~3-thienyi)pyrrolo[3,2~b]pyridin~1 -yl]-N,N- dimethyl-acetamide;

441 N,N-Dimethyl-2-[6-[6-(trifluoromethyl)-2-pyridyl]pyrrolo[3,2 - b]pyridin-1 -yl]acetamide;

■442 N,N-Dimethyl-2-[6-[2-(trifluoromethyl)-4-pyridyl]pyrrolo[3,2 - b]pyridin-1 -yl]acetamide;

443 N,N-Dimethyl-2-[6-[5-(trifluoromethyl)-3-pyridyl]pyrrolo[3,2 - b]pyridin-1 -y!]acetamide;

444 2-[6-(2,6-Difluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide;

445 2-[6-(2-Fluoro-5-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

446 1 -(Azetidiri-1 -yl)-2-[6-[3-(difluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yijeihanone;

447 2-[6-(2,4-Difluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-

N,N-dimethyl-aceiamide;

448 2-[6-(3-Ch!oro-2-f!uoro-pheny!)pyrrolo[3,2-b]pyndin-1 -yl]-N,IM- dimeihyi-aceiamide;

449 2-[6-(3-Ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl- acetamide;

450 2-[6-(3-Fluoropheny!)pyrro!o[3,2-b]pyrid!n-1 -yl]-N,N-d!methyl- aceiamide;

451 1 -(Azetidin-1 -yl)-2-[6-(2-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; Example # Compound Name

452 1 -(Azetidin-1 -yl)-2-[6-(2,4-difluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone;

453 1 -(Azetidin~1 -yl)-2~[6~(3~chloro~2-fiuoro~phenyi)pyrrolo[3,2~ b]pyridin-1 -yijethanone;

454 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(2-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone;

455 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(2,3,4-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone;

456 1 -(Azetidin-1 -yl)-2-[6-(3-chloro-4-fluoro-phenyl)pyrrolo[3,2- bjpyrldin-1 -yijethanone;

457 1 -(3-Fiuoroazetidin-l -yl)-2-[6-(2-fluorophenyl)pyrrolo[3,2- bjpyridin-1 -yijethanone;

458 2-[6-[3-(Difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -ylj-1 -(3- f!uoroazetidln-1 -y!)ethanone;

459 N-Ethyl-N-methyl-2-[6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yljacetamide;

460 2-[6-(2,4-Difluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -ylj-1 -

(3-fluoroazetidin-1 -y!)ethanone;

461 2-[6-(3,4-Difluoropheny!)pyrrolo[3,2-bjpyridin-1 -ylj-N-ethy!-N- methyl-acetamide;

462 ISI-Ethyl-N-methyl-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2- bjpyridin-1 -yljacetamide;

463 1 -(Azetidin-1 -yl)-2-[6-(3-chlorophenyl)pyrrolo[3,2-bjpyridin-1 - yijethanone;

464 N-Ethyl-2-[6-[2-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2 - b]pyridin-1 -yij-N-methyl-acetamide; Example # Compound Name

465 2-[6-(3-Chlorophenyi)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- fluoroazetidin-1 -yl)ethanone;

466 2-[6~(3-Chloro~2-fluoro-phenyl)pyrroio[3,2-b]pyridin~1 -yl]~1 -(3~ fluoroazeiidin-1 -yl)ethanone;

467 2-[6-(3-Chloro-4-fluoro-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- f!uoroazeiidin-1 -y!)ethanone;

468 2-[6-(3-Chloro-4-fluoro-phenyl)pyrro!o[3,2-b]pyridin-1 -y!]-N,N- dimethyi-aeetamide;

469 2-[6-(2,4-Difluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N- ethyl-N-methyl-acetamide;

470 N-Ethyl-N-methyl-2-[6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2 - b]pyridin-1 -yl]acetamide;

471 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(2-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone;

472 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(2-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone;

473 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(m-tolyl)pyrrolo[3,2-bJpyridin-1 - yljethanone;

1 -(Azetidin-1 -yl)-2-[6-(3,5-d if!uorophenyi)-3-fluoro-pyrroio[3,2- bjpyridin~1 -yljethanone;

475 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-[3-

(trifiuoromethyi)phenylJpyrrolo[3,2-b]pyridin-1 -yljethanone;

476 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-[2-fluoro-3- (trifluoromethyl)phenylJpyrrolo[3,2-b]pyridin-1 -yljethanone;

477 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(2 _i 3,4-trifluorophenyl)pyrrolo[3 _i 2- b]pyridin-1 -yljethanone; Example # Compound Name

478 1 -(Azetidin-1 -yl)-2-[6-(3-chlorophenyl)-3-fluoro-pyrrolo[3,2- b]pyridin-1 -y!jeihanone;

479 1 -(Azetidin~1 -yl)-2~[6~(3~chloro~2-fiuoro~phenyi)-3~fluoro~

pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

480 1 -(Azetidin-1 -yl)-2-[6-(2,4-d ifluoro-3-methyl-phenyl)-3-fluoro- pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

481 1 -(Azetidin-1 -yl)-2-[6-(3-chioro-4-f!uoro-pheny!)-3-f!uoro- pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

482 1 -(3-Fluoroazetidin-1 -yl)-2-(3-fluoro-6-phenyl-pyrrolo[3,2- b]pyridin-1 -y!)ethanone;

483 1 -(3-Fiuoroazetidin-l -yl)-2-[3-f!uoro-6-(2-fiuoro-3-methyi- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

484 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-[3-

(trif!uoromethy!)phenyl]pyrroio[3,2-b]pyridin-1 -yl]ethanone;

485 1 -(3-F!uoroazetidin-1 -yl)-2-[3-fluoro-6-[2-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

486 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

487 2-[6-(3,5-Dif!uorophenyi)-3-fluoro-pyrroio[3,2-b]pyridin-1 -yl]-1 - (3~fluoroazetidin~1 -yl)ethanone;

488 2-[6-(2,4-Difluoro-3-methyl-phenyl)-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-fluoroazetidin-1 -yl)ethanone;

489 2-[6-(3-Chloropheny!)-3-fiuoro-pyrro!o[3,2-b]pyridin-1 -yl]-1 -(3- fluoroazetidin~1 -yl)ethanone;

490 2-[6-(3-Chloro-2-fluoro-phenyl)-3-fluoro-pyrrolo[3,2-b]pyrid in-1 - yl]-1 -(3-fluoroazeiidin-1 -yi)ethanone; Example # Compound Name

491 2-[6-(3-Ethylphenyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- fluoroazetidin-1 -yl)ethanone;

492 1 -(3-Fiuoroazetidin-1 ~yl)~2-[3-fluoro-6~(3- fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]eihanone;

493 2-[3-Fluoro-6-(2-fluorophenyi)pyrrolo[3,2-b]pyrid!n-1 -yl]-N,N- dimethyl-acetamide;

■40 "4 2-[3-F!uoro-6-(2-fluoro-3-meihy!-phenyl)pyrrolo[3 _! 2-b]pyridin-1 - yl]-N,N-dimethyl-acetamide;

495 2-(3-Fluoro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-N,N-dimethyl- aceiamide;

496 2-[3-Fluoro-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl- acetamide;

497 1 -(Azetidin-1 -yl)-2-(3-fluoro-6-phenyl-pyrrolo[3,2-b]pyridin-1 - y!)ethanone;

498 1 -(Azetidin-1 -yl)-2-[6-(3-ethylpheny!)-3-fluoro-pyrro!o[3,2- b]pyridin-1 -yijeihanone;

499 2-[3-Fluoro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyrid in-1 - yl]-N,N-dimethyl-acetamide;

500 2-[3-Fiuoro-6-[2-fiuoro-3-(trifiuoromethyi)phenyl]pyrroio[3, 2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide;

501 2-[3-Fluoro-6-(2,3,4-trifluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide;

502 2-[6-(2,4-Difluoro-3-meihy!-phenyl)-3-fiuoro-pyrrolo[3,2- b]pyridin-1 ~yi]~N,IM~dimeinyi-acetamide;

503 2-[6-(3-Chlorophenyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide; Example # Compound Name

504 2-[6-(3-Chloro-4-fluoro-phenyl)-3-fluoro-pyrrolo[3,2-b]pyrid in-1 - yl]-N,N-dimethyl-acetamide;

505 2-[6~(3-Eihyiphenyl)~3-fluoro-pyrrolo[3,2~b]pyridin-1 ~yl]-ISI _! IM- dimethyl-acetamide;

506 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(3-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone;

507 1 -(3-F!uoroazetidin-1 -yl)-2-[3-fluoro-6-(2- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

508 1 -(3-Fluoroazeiidin-1 -yl)-2-[3-fluoro-6-[4-fluoro-3-

(irifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 -yljethanone;

509 2-[6-(3,5-Difluorophenyl)-3-fluoro-pyrrolo[3,2-b]pyridln-1 -ylj- N,N-dimethyl-acetamide;

510 2-[3-Fluoro-6-(3-fluorophenyl)pyrrolo[3,2-b]pyrid!n-1 -yl]-N,N- dimethyl-acetamide;

46 2-[3-Chloro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyrid!n-1 -yl]-N,N- dimethyl-acetamide;

512 2-[3-Chloro-6-(2-fluorophenyl)pyrrolo[3 _i 2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

513 2-[3-Chloro-6-(2-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - yll-N^-dimethyl-acetamide;

514 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-N,N-dimetbyl- acetamide;

515 2-[3-Chloro-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl- aceiamide;

516 2-[3-Chloro-6-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3, 2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; Example # Compound Name

517 2-[3-Chloro-6-[2-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3, 2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide;

518 2-[3~Chtoro-8~(2,3,4~trifluorophenyl)pyrrolo[3,2~b]pyridiri- 1 ~yl]- N,N-dimethyl-acetamide;

519 2-[3-Chloro-6-(2,4-difluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -ylJ-N,N-dimethyl-acetamide;

520 2-[3-Ch!oro-6-(3-ch!oro-4-f!uoro-pheny!)pyrrolo[3,2-b]pyridi n-1 - yl]-N,N-dimethyl-acetamide;

521 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(2-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone; v522 1 -(Azetidin-1 -y!)-2-[3-ch!oro-6-(2-fiuora-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone;

523 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[4-fluoro-3-

(trif!uoromethy!)phenyl]pyrroio[3,2-b]pyridin-1 -yl]ethanone;

524 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[2-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

525 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(2,4-difluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

526 1 -(Azetidin-1 -y!)-2-[3-ch!oro-6-(3-chloropheny!)pyrrolo[3,2- b]pyridin~1 -yljethanone;

527 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3-chloro-4-fiuoro- phenyi)pyrrolo[3,2-b]pyridin-1 -yljethanone;

528 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3-chioro-2-fluoro- phenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone;

529 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[3-

(difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yljethanone; Example # Compound Name

530 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone;

531 2-[3~Cbloro-6~(3-fluorophenyl)pyrrolo[3 _! 2-b]pyridin~1 -yl]~IM,N- dimethyl-acetamide;

532 1 -(Azeiidin-1 -yl)-2-[3-chloro-6-(3,5-difluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone;

533 1 -(Azetidin-1 -yl)-2-[3-ch!oro-6-(3-ethy!phenyl)pyrrolo[3 _! 2- b]pyridin-1 -yljethanone;

534 2-[3-Chloro-6-(3-chlorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

535 2-[3-Cbloro-6-(2-fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 -yl]-1 -(3- fluoroazeiidin-1 -yljethanone;

536 2-[3-Chloro-6-(2-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - yl]-1 -(3-fluoroazetidin-1 -yl)ethanone;

537 2-[3-Chloro-6-(3 _! 5-difluorophenyl)pyrrolo[3,2-b]pyrid!n-1 -yl]-1 - (3-fluoroazetidin-1 ~yl)ethanone;

538 2-[3-Chloro-6-[2-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3, 2- b]pyridin-1 -yl]-1 -(3-fluoroazetidin-1 -yl)ethanone;

539 2-[3-Chloro-6-(2,4-difluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin~1 -yl]-1 ~(3~fluoroazetidin~1 -yl)ethanone;

540 2-[3-Chloro-6-(3-chloro-4-fluoro-phenyl)pyrrolo[3,2-b]pyridi n-1 - yl]-1 -(3-fluoroazetidin-1 -yl)ethanone;

541 2-[3-Chloro-6-(3-chloro-2-fluoro-phenyl)pyrrolo[3,2-b]pyridi n-1 - yl]-1 -(3~fluoroazetidin-1 ~yl)ethanone;

542 2-[3-Chloro-6-(3-ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- fluoroazetidin-1 -yl)ethanone; Example # Compound Name

543 2-[3-Chloro-6-(3-fluorophenyl)pyrrolo[3 _i 2-b]pyridin-1 -yl]-1 -(3- fluoroazetidin-1 -yl)ethanone;

544 2-[3~Chloro-6~(3-chloro-2~fluoro~phenyl)pyrrolo[3,2~b]pyridi ri-1 ~ yl]-N,N-dimethyl-acetamide;

545 2-[3-Chloro-6-(3-chlorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- f!uoroazeiidin-1 -y!)ethanone;

546 2-[3-Ch!oro-6-[3-(dif!uoromeihy!)phenyl]pyrro!o[3,2-b]pyridi n-1 - yl]-1 -(3-fluoroazeiidin-1 -yl)ethanone;

547 1 -(Azetidin-1 -yl)-2-[3-fluoro-2-methyl-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone;

548 1 -(Azetidin-1 -y!)-2-[8-(3,4-dif!uoropheny!)-3-meihy!-pyrrolo[3,2- b]pyridin-1 -yijethanone;

549 2-[8-(3 _i 4-Difiuorophenyl)-3-methyi-pyrrolo[3,2-b]pyrid!n-1 -yl]- N,N-dimethyl-acetamide;

550 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -yijethanone;

551 2-[6-(3,4-Difluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]-1 -

(3-fiuoroazetidin-1 -y!)ethanone;

552 1 -(Azetidin-1 -yl)-2-[3-methyl-6-[3-

(trifiuoromeihyiiphenyljpyrrolo^^-bjpyridin-l -yijethanone;

553 N,N-Dimethyl-2-[3-methyl-6-[3-

{trifluoromethyl)phenyljpyrrolo[3,2-b]pyridin-1 -yljacetaniide;

554 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-[3- (trifluoromethyl)phenylJpyrrolo[3,2-b]pyridin-1 -yijethanone;

555 2-[6-(3 _! 5-Difluorophenyl)-3-methyl-pyrrolo[3,2-bJpyridin-1 -yl]-

N,N-dimethyl-acetamide; Example # Compound Name

556 1 -(Azetidin-1 -yl)-2-[6-(3,5-difluorophenyl)-3-methyl-pyrrolo[3,2- b]pyridin-1 -y!jeihanone;

557 2-[6~(3 _! 5~Difluorophenyl)~3-methyl~pyrroio[3,2-b]pyridin~1 -yl]~N- ethyl-N-methyl-acetamide;

558 2-[6-(4-Fluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

559 N-Eihy!-2-[6-(4-f!uoropheny!)-3-meihy!-pyrrolo[3,2-b]pyridin -1 - yl]-N-methyi-acetamide;

560 N-Ethyl-2-[6-(2-fluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3,2 - b]pyridin-1 -yl]-N-methyl-acetamide;

561 1 -(Azetidin-1 -y!)-2-[6-(2-f!uoro-3-methyl-pheny!)-3-meihy!- pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

562 2-[6-(2-Fiuoro-3-meihyl-phenyl)-3-methyi-pyrrolo[3,2-b]pyrid in- 1 -yl]-N,N-dimethyl-acetamide;

563 1 -(3-F!uoroazetidin-1 -yl)-2-[6-(2-f!uoro-3-methyl-pheny!)-3- methyl-pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

564 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(2-fluoro-3-methyl-phenyl)-3- methyl-pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

565 2-[6-(2-F!uoro-3-methyl-pheny!)-3-meihy!-pyrrolo[3,2-b]pyrid in- 1 -yl]-1 -pyrrolidin~1 -yl~eihanone;

566 2-[6-(4-Fluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3,2-b]pyrid in-

1 -yl]-N,N-dimethyl-acetamide;

567 2-[3-fVfeihy!-6-[3-(tr!f!uoromeihy!)phenyl]pyrro!o[3,2-b]pyr id!n-1 - yl]-1 -pyrrolidin~1 -yl~eihanone;

568 N-Ethyl-N-methyl-2-[3-methyl-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]acetamide; Example # Compound Name

569 1 -(3,3-Difluoroazetidin-1 -yl)-2-[3-methyl-6-[3-

(irifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 -y!]eihanone;

570 1 -(Azetidin-1 -yl)-2-[3-methyl-6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

571 N.N-Dimeihyl^-p-meihyl-e^S^^-trifluorophenylipyrrolo^^- bjpyridin-1 -yljaceiamide;

572 N,N-Dimethyl-2-[3-methyl-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yl]acetamide;

573 N,N-Dimethyl-2-[3-methyl-6-(4-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -y!]acetamide;

574 1 -(Azetidin-1 -y!)-2-[3-methyl-6-(4-methy!-2-thieny!)pyrrolo[3, 2- b]pyridin-1 -yijethanone;

575 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(4-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yijethanone;

576 N,N-Dimethyl-2-(3-methyl-6-phenyl-pyrrolo[3,2-b]pyridin-1 - yl)acetamide;

577 N-Ethyl-N-methyl-2-(3-methyl-6-phenyl-pyrroio[3,2-b]pyridin- 1 - yl)acetamide;

578 1 -(3-Fiuoroazetidin-1 -yl)-2-(3-methyl-6-phenyi-pyrrolo[3,2- b]pyridin~1 -yl)ethanone;

579 1 -(3,3-Difluoroazetidin-1 -yl)-2-(3-methyl-6-phenyl-pyrrolo[3,2- b]pyridin-1 -yl)ethanone;

580 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(4-fluoro-3-methyl-phenyl)-3- methyl-pyrrolo[3,2-b]pyridin-1 -yijethanone;

581 1 -(Azetidin-1 -yl)-2-[3-methyl-6-(m-tolyl)pyrrolo[3,2-bJpyridin-1 - yijethanone; Example # Compound Name

582 1 -(Azetidin-1 -yl)-2-[3-methyl-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

583 N.N-Dimeihyl^-p-methyi-S^.S^-trifiuoropheny^pyrrolop^- b]pyridin-1 -yl]acetamide;

584 N-Eihyl-N-methyl-2-[3-methyi-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide;

585 1 -(Azetidin-1 -yl)-2-[6-[2-f!uoro-3-(irifluoromethyl)pheny!]-3- methyl-pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

586 2-[6-[2-Fluoro-3-(trifluoromethyl)phenyl]-3-methyl-pyrrolo[3 ,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide;

587 N-Ethyl-2-[6-[2-fluoro-3-(trifluoromethyl)phenyl]-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]-N-methyl-acetamide;

588 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

589 1 -(3-Fiuoroazetidin-1 -yl)-2-[6-[2-fluoro-3-

(irifluoromethyl)phenyi]~3~methyl-pyrrolo[3,2~b]pyridin-1 ~ yl]ethanone;

590 2-[6-[2-Fluoro-3-(trifluoromethyl)phenyl]-3-methyl-pyrrolo[3 ,2- b]pyridin-1 -yl]-1 -pyrroiidin-1 -yl-eihanone;

591 2-[3-!Vlethyl-6-(2,3,4-trifluorophenyi)pyrroio[3,2-b]pyridin -1 -yl]- 1 -pyrroiidin~1 -yi-eihanone;

592 1 -(Azetidin-1 -yl)-2-[6-(2-fiuorophenyl)-3-methyi-pyrrolo[3,2- bjpyridin-1 -yljethanone;

593 2-[6-(2-Fiuoropheny!)-3-methyi-pyrro!o[3,2-b]pyridin-1 -yi]-N,N- dimethyl-acetamide;

594 N-Ethyl-2-[6-(2-fluorophenyl)-3-methyi-pyrrolo[3,2-b]pyridin -1 - yl]-N-methyl-acetamide; Example # Compound Name

595 1 -(3,3-Difluoroazeiidin-1 -yl)-2-[6-[2-fluoro-3- (trifluoromethyl)phenyl]-3-methyl-pyrrolo[3,2-b]pyridin-1 - yljethanone;

596 1 -(3,3-Difiuoroazetidin-1 -yl)~2-[3-methyl-6-(2,3 _! 4~

trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

597 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(2-fluorophenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

598 1 -(3-F!uoroazetidin-1 -yl)-2-[3-methyl-6-(3,4,5- irifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]eihanone;

599 2-[3-Chloro-6-(2,5-dimethyl-3-thienyl)pyrrolo[3,2-b]pyridin- 1 -yl]-

N,N-dimethyl-aceiamide;

600 2-[3-Chloro-6-[3-(irifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 - yl]-N,N-dimethyl-acetamide;

601 2-[3-Chloro-6-[6-(trifluoromethyl)-2-pyridyl]pyrrolo[3,2-b]p yridin- 1 -yl]-N,N-dimethyl-acetamide;

602 2-[3-Ch!oro-6-(5-ch!oro-4-methy!-2-thieny!)pyrrolo[3,2-b]pyr idin- 1 -yl]-N,N-dimeihyl-acetamide;

603 2-[3-Chloro-6-[5-(trifluoromethyl)-2-thienyl]pyrrolo[3,2-b]p yridin-

1 -yl]-N,N-dimeihy!-acetamide;

604 2-[6-(Benzothiophen-2-yl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide;

605 2-[3-Fluoro-6-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3, 2- b]pyridin-1 -yl]-IM,N-dimethyl-acetamide;

606 2-[6-(3-Chloro-2-fluoro-phenyl)-3-f!uoro-pyrrolo[3 _! 2-b]pyridin-1 - yl]-N,N-d!methyl-acetamide;

607 1 -(3-Fluoroazeiidin-1 -yl)-2-[3-fluoro-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone; Example # Compound Name

608 2-[6-(3-Chioro-4-fluoro-phenyl)-3-fluoro-pyrrolo[3,2-b]pyrid in-1 - yl]-1 ~(3-fluoroazetidin~1 -yl)ethanone;

609 1 -(Azeiidin~1 -yl)-2~(3-[ ³ H]~6-(4~fluoro~3-methylphenyl)-1 H- pyrrolo[3,2-b]pyridin-1 -yl)ethanone;

610 2-[2-Deuterio-6-(4-fluoro-3-methyi-phenyl)pyrro!o[3,2-b]pyri din- 1 ~yl]-N,IM-dimethyl-aceiamide;

61 1 2-[6-(3,5-Difluorophenyl)-3-(irifluoromethyl)pyrro!o[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide;

612 3-Chloro-1 -(3-pyridylmethyl)-6-[3-

(trifiuoromeihy^phenyljpyrrotop^-bjpyridine;

613 1 -(Pyridazin-3-ylmeihy!)-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridine;

614 3-Chloro-6-(4-fluoro-3-methyl-phenyl)-1 -(pyridazin-3- ylmethyl)pyrrolo[3,2-b]pyridine;

615 3-Chloro-1 -(pyridazin-3-ylmethyl)-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridine;

616 2-[6-(4-Fluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3,2-b]pyrid in- 1 -yl]-1 -pyrrolidin-1 -y!-ethanone;

617 N-Ethyl-2-[6-(4-fluoro-3-meihy!-phenyl)-3-methyl-pyrro!o[3,2 - b]pyridin-1 -yl]-N-methyl-acetamide;

618 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(4-fluoro-3-methyl-phenyl)-3- meihy!-pyrro!o[3,2-b]pyridin-1 -yl]ethanone;

619 2-[6-(3,4-Difluorophenyl)-3-methyl-pyrro!o[3,2-b]pyridin-1 -y!]-1 - pyrrolidin-1 -yl-ethanone;

620 2-[6-(3,4-Difluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]-N- ethyl-N-methyl-acetamide; Example # Compound Name

621 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(3,4-difluorophenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

622 2-[6~(2,4~Difluoro-3~meihyi-phenyl)~3-methyl~pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide;

623 2-[6-(3,5-Difluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrrolidin~1 -yl~eihanone;

624 2-[6-(2,4-Difluoro-3-meihy!-phenyl)-3-methyl-pyrrolo[3,2- b]pyridin-1 -yl]-1 -pyrroiidin-1 -yl-eihanone;

625 2-[6-(2,4-Difiuoro-3-methyl-phenyi)-3-meihyi-pyrrolo[3 _! 2- b]pyridin-1 -yl]-N-ethyl-N-methyl-acetamide;

626 1 -(3,3-Difluoroazeiidin-1 -y!)-2-[6-(2,4-difluoro-3-meihy!-phenyl)- 3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

627 1 -(Azetidin-1 -yl)-2-[6-(2,4-difluoro-3-methyl-phenyl)-3-methyl- pyrrolo^^-bjpyridin-l -yljethanone;

628 2-[6-(5-Chloro-2-ihieny!)-3-methyl-pyrro!o[3,2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide;

629 2-[6-(2,4-Difluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-f!uoroazetidin-1 -y!)ethanone;

630 N-Ethyl-N-methyl-2-[3-methyl-6-(5-methyl-2-thienyl)pyrrolo[3 ,2- b]pyridin-1 -yl]acetamide;

631 2-[3-Methyl-6-(5-methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrrolidin-1 -y!-ethanone;

632 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[3-methyl-6-(5-methyl-2- ihienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone;

633 1 -(Azetidin-1 -yl)-2-[3-methyl-6-(5-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone; Example # Compound Name

634 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(5-methyl-2- thienyl)pyrroio[3,2~b]pyridin-1 ~yl]ethanone;

635 2-[6~(3,5~Difiuorophenyl)~3-methyi~pyrrolo[3,2-b]pyridin~1 -yl]~1 - (3-fluoroazetidin-1 -yl)ethanone;

636 2-[6-(5-Chloro-2-thienyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]-1 - (3-fiuoroazetidin-1 ~yl)ethanone;

637 N,N-Dimethyl-2-[3-methyl-6-(5-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yl]acetarnide;

638 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(2-fluorophenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yijethanone; and

639 2-[6-[5-(Difluoromethyl)-2-thieny!]pyrrolo[3,2-b]pyridin-1 -y!]- N,N-dimethyl-acetamide; and p harmaceuiically acceptable salts, N-oxides, or solvates thereof.

An additional embodiment of the invention is a pharmaceutical composition comprising:

(A) an effective amount of at least one compound selected from compounds of Formula (I):

R

wherein

R is selected from the group consisting of: H, ³ H, halo, C _h alk !, and Ci- 3haioalkyl;

R ² is selected from the group consisting of: phenyl optionally substituted with one, two, or three members independently selected from: halo, C _ 5alkyi, and Ci-shaioalkyi; pyridinyl optionally substituted with halo, d. salkyi, C-i-shaloalkyl, and -CN; thiazoiyi optionally substituted with Ci. salkyi; benzoihiophenyl; and thienyi optionally substituted with one, two or three members independently selected from: halo, C _h alky!, and Ci- shaloalkyl;

R ³ is selected from the group consisting of:

(a) wherein ring A is a 4-7 membered heterocycloaikyl

optionally containing an additional oxygen heteroatom selected from the group consisting of: azetidinyl optionally substituted with one or two members independently selected from the group consisting of: halo, C _h alky!, Ci-shaioalkyi, CH ₂ OH, Ci-saikoxy, OH, and CN;

pyrroiidinyi optionally substituted one or two members independently selected from the group consisting of: halo, Ci _-5 aikyl, Ci-saikox , and OH; morpholino optionally substituted one or two Ci. ₅ a!kyl members; piperidinyi optionally substituted with one or two members

independently selected from the group consisting of: halo, C-i-salkyl, Ci-shaioalkyi, Ci-saikoxy, and OH; 3-azabicycio[3.1 .0]hexan-3-yi; 5- azaspiro[2.3]hexan-5-yl; and pyrroiidin-3-one; or

(b) wherein R ^3a is H, or Ci-salkyl;

and R is selected from the group consisting of: C -sa!kyi optionally substituted with OH, halo, or OCH ₃ ; Ci-shaioalkyi; benzyl;

CH ₂ cyciopropyi; cyclopropyi optionally substituted with and cyciobutyl; or

(c) ^r3 ° wherein R ^3c is selected from the group consisting of:

cyclopropyi; cyciobutyl; pyrimidinyl optionally substituted with halo; pyridinyl; pyridazinyl; furanyl optionally substituted with Ci-shaioalkyi; oxazolyi; isoxazoiyi optionally substituted with C _h alky!; oxadiazoiyi optionally substituted with Ci _-5 a!kyl; pyrazolyl optionally substituted with Ci- ₅ aikyl; triazolyl optionally substituted with C _h alky!;

tetrahydrofuranyi; tetrahydropyranyi; oxetanyi; and oxiranyl; or wherein R is CH -cyciopropyl or cyciobutyl; or wherein R ^e is selected from the group consisting of: OH, .. ₅ alkyl, cyclopropyi, cyciobutyl, and phenyl optionally substituted th one halo substifuent; or

(f) Ci _-5 aikyl optionally substituted with OH or Ci _-5 alkoxy; CH ₂ S(CH ₃ );

CH ₂ (S=0)GH ₃ ; CH ₂ (S0 ₂ )CH ₃ ; and CH ₂ CH ₂ (C=0)CH ₃ ; or

and

R ⁴ is H, ² H or Ci. ₃ alkyl,

and pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (!);

and (B) at least one pharmaceutically acceptable excipient.

An additional embodiment of the invention is a pharmaceutical composition comprising and effective amount of at least one compound of Formula (!!A), as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (!IA), pharmaceutically acceptable prodrugs of compounds of Formula (MA), and pharmaceutically active metabolites of Formula (!IA); and at least one pharmaceutically acceptable excipient.

An additional embodiment of the invention is a pharmaceutical composition comprising and effective amount of at least one compound of Formula (MB), as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (MB), pharmaceutically acceptable prodrugs of compounds of Formula (MB), and pharmaceutically active metabolites of Formula (MB); and at least one pharmaceutically acceptable excipient. An additional embodiment of the invention is a pharmaceutical composition comprising and effective amount of at least one compound in Table 1 , as well as pharmaceutically acceptable salts, N-oxides or solvates of compounds of Table 1 , pharmaceutically acceptable prodrugs of compounds of Table 1 , and pharmaceutically active metabolites of Table 1 ; and at least one pharmaceutically acceptable excipient.

Also within the scope of the invention are enantiomers and

diastereomers of the compounds of Formula (I) (as well as Formulas (II), (IIA), (MB), (III), (IV), (V), and (V!)), Also within the scope of the invention are the pharmaceutically acceptable salts, N-oxides or solvates of the compounds of Formula (I) (as well as Formulas (II), ( A), (MB), (III), (IV), (V), and (V!)), Also within the scope of the invention are the pharmaceutically acceptable prodrugs of compounds of Formula (I) (as well as Formulas (II), (HA), (MB), (Ml), (IV), (V), and (VI)), and pharmaceutically active metabolites of the compounds of Formula (I) (as well as Formulas (II), (MA), (MB), (III), (IV), (V), and (VI)).

Also within the scope of the invention are isotopic variations of compounds of Formula (I) (as well as Formulas (II), (l!A), (MB), (Ml), (IV), (V), and (VI)), such as, e.g. , deuterafed compounds of Formula (I). Also within the scope of the invention are the pharmaceutically acceptable salts, N-oxides or solvates of the isotopic variations of the compounds of Formula (I) (as well as Formulas (II), (MA), (MB), (III), (IV), (V), and (V!)). Also within the scope of the inventin are the pharmaceutically acceptable prodrugs of the isotopic variations of the compounds of Formula (I) (as well as Formulas (II), (HA), (MB), (III), (IV), (V), and (VI)), and pharmaceutically active metabolites of the isotopic variations of the compounds of Formula (I) (as well as Formulas (II), (MA), (MB), (III), (IV), (V), and (V!)).

An additional embodiment of the invention is a method of treating a subject suffering from or diagnosed with a disease, disorder, or medical condition mediated by NR2B receptor activity, comprising administering to a subject in need of such treatment an effective amount of at least one compound selected from compounds of Formula (I):

wherein

R is selected from the group consisting of: H, ³ H, halo, Chalky!, and Ci- 3haioalkyl;

R ² is selected from the group consisting of: phenyl optionally substituted with one, two, or three members independently selected from: halo, C - 5alkyi, and Ci-shaloalkyl; pyridinyl optionally substituted with halo, d. 5alkyi, Ci-shaloalkyl, and -CN; thiazoiyi optionally substituted with Ci- 5alkyi; benzothiophenyi; and thienyl optionally substituted with one, two or three members independently selected from: halo, d-saikyi, and Ci- shaloalkyl;

R ³ is selected from the group consisting of:

(a) in ring A is a 4-7 membered heterocycloaikyl

optionally containing an additional oxygen heteroatom selected from the group consisting of: azetidinyl optionally substituted with one or two members independently selected from the group consisting of: halo, Ci-saikyl, Ci-shaloalkyl, CH ₂ OH, Ci-saikoxy, OH, and CN;

pyrroiidinyl optionally substituted one or two members independently selected from the group consisting of: halo, C1.5alk.yl, Ci-saikoxy, and OH; morpholino optionally substituted one or two Ci _-5 alkyl members; piperidinyi optionally substituted with one or two members

independently selected from the group consisting of: halo, Ci-salkyl, Ci-shaloalkyl, Ci-saikoxy, and OH; 3-azabicyclo[3.1 .0]hexan-3-yl; 5- azaspiro[2.3]hexan-5-yl; and pyrroiidin~3-one; or

(b) wherein R ^3a is H, or C _-5 a and R ³ is selected from the group consisting of: C _1-5 alkyl optionally substituted with OH, halo, or OCH ₃ ; C-i-shaloalkyl; benzyl;

CH ₂ cyciopropyl; cyclopropyl optionally substituted with C-i-salkyl; and cyclobutyl; or

(c) ^R ³⁰ wherein R ^3c is selected from the group consisting of:

cyclopropyl; cyclobutyl; pyrimidinyl optionally substituted with halo; pyridinyl; pyridazinyl; furanyl optionally substituted with Ci-shaioalkyi; oxazolyi; isoxazoiyl optionally substituted with Chalky!; oxadiazoiyi optionally substituted with C-i-sa!kyi; pyrazolyl optionally substituted with d-sa!kyl; friazolyl optionally substituted with C halky!;

tetrahydrofuranyl; tetrahydropyranyi; oxetanyl; and oxiranyl; or

(d) wherein R ^3d is CH ₂ -cyciopropyi or cyclobutyl; or

(e) wherein R ^3e is selected from the group consisting of: OH, Ci. ₅ a!kyl, cyclopropyl, cyclobutyl, and phenyl optionally substituted with one halo substituent; or

(f) Ci -saikyl optionally substituted with OH or d -salkoxy; CH ₂ S(CH ₃ );

CH ₂ (S=O)CH ₃ ; CH ₂ (SO ₂ )CH ₃ ; and CH ₂ CH ₂ (C=Q)CH ₃ ; or

(g)

and

R ⁴ is H, ² H or C^a!ky!:

and pharmaceutically acceptable salts, N-oxides, or solvates thereof, to a subject in need thereof.

An additional embodiment of the invention is a method of treating a subject suffering from or diagnosed with a disease, disorder, or medical condition mediated by NR2B receptor activity, comprising administering to a subject in need of such treatment an effective amount of at least one compound selected from compounds of Formula (I) (as well as Formulas (II), (ΠΑ), (MB), (III), (IV), (V), and (VI)), enantiomers and diasiereromers of the compounds of Formula (!), isotopic variations of the compounds of Formula (I), and pharmaceutically acceptable salts of all of the foregoing.

In preferred embodiments of the inventive method, the disease, disorder, or medical condition is selected from: neurologic and psychiatric disorders including, but not limited to: (1 ) mood disorders and mood affective disorders; (2) neurotic, stress-related and somatoform disorders including anxiety disorders; (3) disorders of psychological development; (4) behavioral syndromes associated with physiological disturbances and physical factors; (5) extrapyramidal and movement disorders; (6) episodic and paroxysmal disorders, epilepsy; (7) pain; (8) forms of neurodegeneration; (9)

cerebrovascular diseases, acute and chronic; and any sequelae of cerebrovascular diseases.

Examples of mood disorders and mood affective disorders that can be treated according to the present invention include, but are not limited to, bipolar disorder I depressed, hypomanic, manic and mixed form; bipolar disorder II; depressive disorders, such as single depressive episode or recurrent major depressive disorder, minor depressive disorder, treatment- resistant depression, depressive disorder with postpartum onset, depressive disorders with psychotic symptoms; persistent mood disorders, such as cyclothymia, dysthymia, euthymia; and premenstrual dysphoric disorder.

Examples of disorders belonging to the neurotic, stress-related and somatoform disorders that can be treated according to the present invention include, but are not limited to, anxiety disorders, general anxiety disorder, panic disorder with or without agoraphobia, specific phobia, social anxiety disorder, chronic anxiety disorders; obsessive compulsive disorder; reaction to sever stress and adjustment disorders, such as post-traumatic stress disorder (PTSD); other neurotic disorders such as depersonaiisation- derealisation syndrome.

Examples of disorders of psychological development that can be treated according to the present invention include, but are not limited to pervasive developmental disorders, including but not limited to Asperger ^' s syndrome and Rett's syndrome, autistic disorders, childhood autism and overactive disorder associated with mental retardation and stereotyped movements, specific developmental disorder of motor function, specific developmental disorders of scholastic skills.

Examples of behavioral syndromes associated with physiological disturbances and physical factors according to the present invention include, but are not limited to mental and behavioural disorders associated with childbirth, including but not limited to postnatal (postpartum) and prenatal depression; eating disorders, including but not limited to anorexia nervosa, bulimia nervosa, pica and binge eating disporder.

Examples of extrapyramidal and movement disorders that can be treated according to the present invention include, but are not limited to Parkinson's disease; second Parkinsonism, such as postencephalitic

Parkinsonism; Parkinsonism comprised in other disorders; Lewis body disease; degenerative diseases of the basal ganglia; other extrapyramidal and movement disorders including but not limited to tremor, essential tremor and drug-induced tremor, myoclonus, chorea and drug-induced chorea, drug- induced tics and tics of organic origin, drug-induced acute dystonia, drug- induced tardive dyskinesia, L-dopa-induced dyskinesia; neuroleptic-induced movement disorders including but not limited to neuroleptic malignant syndrome (NMS), neuroleptic induced parkinsonism, neuroleptic-induced early onset or acute dyskinesia, neuroleptic-induced acute dystonia, neuroleptic-induced acute akathisia, neuroleptic-induced tardive dyskinesia, neuroleptic-induced tremor; restless leg syndrome, Stiff-man syndrome.

Further examples of movement disorders with malfunction and/or degeneration of basal ganglia that can be treated according to the present invention include, but are not limited to dystonia including but not limited to focal dystonia, multiple-focal or segmental dystonia, torsion dystonia, hemispheric, generalised and tardive dystonia (induced by

psychopharmacological drugs). Focal dystonia include cervical dystonia (torticolli), blepharospasm (cramp of the eyelid), appendicular dystonia (cramp in the extremities, like the writer's cramp), oromandibular dystonia and spasmodic dysphonia (cramp of the vocal cord); Examples for episodic and paroxysmal disorders that can be treated according to the present invention include, but are not limited to epilepsy, including localization-related (focal)(partial) idiopathic epilepsy and epileptic syndromes with seizures of localized onset, localization-related (focal)(partial) symptomatic epilepsy and epileptic syndromes with simple partial seizures, localization-related (focai)(partiai) symptomatic epilepsy and epileptic syndromes with complex partial seizures, generalized idiopathic epilepsy and epileptic syndromes including but not limited to myoclonic epilepsy in infancy, neonatal convulsions (familial), childhood absence epilepsy (pyknolepsy), epilepsy with grand mal seizures on awakening, absence epilepsy, myoclonic epilepsy (impulsive petit mal) and nonspecific atonic, clonic, myoclonic, tonic, tonic-clonic epileptic seizures.

Further examples of epilepsy that can be treated according to the present invention include, but are not limited to epilepsy with myoclonic absences, myocionic-astatic seizures, infantile spasms, Lennox-Gastaut syndrome, Salaam attacks, symptomatic early myoclonic encephalopathy, West's syndrome, petit and grand mal seizures; status epilepticus.

Examples of pain include, but are not limited to pain disorders related to psychological factors, such as persistent somatoform disorders; acute, chronic and chronic intractable pain, headache; acute and chronic pain related to physiological processes and physical disorders including but not limited to back pain, tooth pain, abdominal pain, low back pain, pain in joints; acute and chronic pain that is related to diseases of the musculoskeletal system and connective tissue including, but not limited to rheumatism, myalgia, neuralgia and fibromyalgia; acute and chronic pain that is related to nerve, nerve root and plexus disorders, such as trigeminal pain, postzoster neuralgia, phantom limb syndrome with pain, carpal tunnel syndrome, lesion of sciatic nerve, diabetic mononeuropathy; acute and chronic pain that is related to polyneuropathies and other disorders of the peripheral nervous system, such as hereditary and idiopathic neuropathy, inflammatory polyneuropathy, polyneuropathy induced by drugs, alcohol or toxic agents, polyneuropathy in neoplastic disease, diabetic polyneuropathy. Examples of diseases that include forms of neurodegeneration include, but are not limited to, acute neurodegeneration, such as intracranial brain injuries, such as stroke, diffuse and local brain injuries, epidural, subdural and subarachnoid haemorrhage, and chronic neurodegeneration, such as

Alzheimer's disease, Huntington's disease, multiple sclerosis and ALS.

Examples of cerebrovascular diseases include, but are not limited to, subarachnoid haemorrhage, intracerebral haemorrhage and other

nontraumatic intracranial haemorrhage, cerebral infarction, stroke, occlusion and stenosis or precerebral and cerebral arteries, not resulting in cerebral infarction, dissection of cerebral arteries, cerebral aneurysm, cerebral atherosclerosis, progressive vascular leukoencephalopathy, hypertensive encephalopathy, nonpyogenic thrombosis of intracranial venous system, cerebral arteritis, cerebral amyloid angiopathy and sequelae of

cerebrovascular diseases,

In some embodiments, administration of a compound of the invention, or pharmaceutically acceptable salt thereof, is effective in preventing the disease; for example, preventing a disease, condition or disorder in an individual who may be predisposed to the disease, condition or disorder but does not yet experience or display the pathology or symptomatology of the disease.

Additional embodiments, features, and advantages of the invention will be apparent from the following detailed description and through practice of the invention.

The invention may be more fully appreciated by reference to the following description, including the following glossary of terms and the concluding examples. For the sake of brevity, the disclosures of the publications, including patents, cited in this specification are herein

incorporated by reference.

As used herein, the terms "including", "containing" and "comprising" are used herein in their open, non-limiting sense.

The term "alkyi" refers to a straight- or branched-chain alkyi group having from 1 to 12 carbon atoms in the chain. Examples of alkyi groups include methyl (Me, which also may be structurally depicted by the symbol, 7"), ethyl (Et), n-propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl (tBu), pentyl, isopentyl, tert-pentyl, hexyl, isohexyl, and groups that in light of the ordinary skill in the art and the teachings provided herein would be considered equivalent to any one of the foregoing examples. The term C _h alk ! as used here refers to a straight- or branched-chain alkyl group having from 1 to 3 carbon atoms in the chain. The term Cr ₅ aiky! as used here refers to a straight- or branched-chain alkyl group having from 1 to 5 carbon atoms in the chain.

The term "alkoxy" includes a straight chain or branched alkyl group with a terminal oxygen linking the alkyl group to the rest of the molecule. Alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-butoxy, pentoxy and so on.

The term "aryl" refers to a monocyclic, aromatic carbocycle (ring structure having ring atoms that are all carbon) having 6 atoms per ring.

(Carbon atoms in the aryl groups are sp ² hybridized.)

The term "phenyl" represents the following moiety:

The term "thienyl" represents the following moiety:

The term "heteroaryl" refers to a monocyclic or fused bicyclic heterocycie (ring structure having ring atoms selected from carbon atoms and up to four heteroatoms selected from nitrogen, oxygen, and sulfur) having from 3 to 9 ring atoms per heterocycie. Illustrative examples of heteroaryl groups include the following entities, in the form of properly bonded moieties:

Those skilled in the art will recognize that the species of heteroaryl, cycloalkyi, aryl and heterocycioalkyi groups listed or illustrated above are not exhaustive, and that additional species within the scope of these defined terms may also be selected.

A "heterocycioaikyi" refers to a monocyclic ring structure that is saturated or partially saturated and has from 4 to 7 ring atoms per ring structure selected from carbon atoms and up to two heteroatoms selected from nitrogen, oxygen, and sulfur. The ring structure may optionally contain up to two oxo groups on sulfur ring members. Illustrative entities, in the form of properly bonded moieties, include:

The term "cyano" refers to the group -CM.

The term "cycloalkyi" refers to a saturated or partially saturated, monocyclic, fused poiycyciic, or spiro polycyclic carbocycie having from 3 to 12 ring atoms per carbocycie. Illustrative examples of cycloalkyi groups include the following entities, in the form of properly bonded moieties:

The term "halo" represents chloro, fluoro, brorno or iodo.

The term "perhaioalkyi" or "haloaikyl" refers to a straight- or branched- chain aikyl group having from 1 to 5 carbon atoms in the chain optionally substituting hydrogens with halogens. The term "Ci~3haioalkyl" as used here refers to a straight- or branched-chain aikyl group having from 1 to 3 carbon atoms in the chain, optionally substituting hydrogens with halogens. The term "Ci-shaloaikyi" as used here refers to a straight- or branched-chain alkyi group having from 1 to 5 carbon atoms in the chain, optionally substituting hydrogens with halogens. Examples of "perhaioalkyi", "haloaikyl" groups include trifluoromethyi (CF ₃ ), difiuoromethyi (CF ₂ H), monofluoromethyl (CH ₂ F), pentafiuoroethyl (CF ₂ CF ₃ ), tetrafluoroethyi (CHFCF ₃ ),monofluoroethyl (CH ₂ CH ₂ F), trifluoroetbyi (CH ₂ CF ₃ ), tetrafiuorotrifluoromethylethyl (-CF(CF ₃ ) ₂ ), and groups that in light of the ordinary skill in the art and the teachings provided herein would be considered equivalent to any one of the foregoing examples.

The term "perhaioa!koxy" or "haioalkoxy" refers to a straight- or branched-chain alkoxy group having from 1 to 5 carbon atoms in the chain optionally substituting hydrogens with halogens. Examples of perhaloaikoxy groups include trifiuoromethoxy (GCF ₃ ), difiuoromethoxy (OCF ₂ H),

monofluoromethoxy (OCH ₂ F), monofiuoroethoxy (OCH ₂ CH ₂ F),

pentafluoroethoxy (OCF ₂ CF ₃ ), tetrafluoroethoxy (OCHFCF ₃ ), trifluoroethoxy (OCH ₂ CF ₃ ), tetrafiuorotrifluoromethylethoxy (-OCF(CF ₃ ) ₂ ), and groups that in light of the ordinary skill in the art and the teachings provided herein would be considered equivalent to any one of the foregoing examples.

The term "substituted" means that the specified group or moiety bears one or more substituents. The term "unsubstitufed" means that the specified group bears no substituents. The term "optionally substituted" means that the specified group is unsubstituted or substituted by one or more substituents. Where the term "substituted" is used to describe a structural system, the substitution is meant to occur at any valency-allowed position on the system. In cases where a specified moiety or group is not expressly noted as being optionally substituted or substituted with any specified substituenf, it is understood that such a moiety or group is intended to be unsubstituted.

The terms "para", "meta", and "ortho" have the meanings as

understood in the art. Thus, for example, a fully substituted phenyl group has substituents at both "ortho"(o) positions adjacent to the point of attachment of the phenyl ring, both "meta" (m) positions, and the one "para ^" (p) position across from the point of attachment. To further clarify the position of substituents on the phenyl ring, the 2 different ortho positions will be designated as ortho and ortho' and the 2 different meta positions as meta and meta' as illustrated below. ortho

When referring to substituents on a pyridyl group, the terms "para", "meta", and "ortho" refer to the placement of a substituent relative to the point of attachment of the pyridyl ring. For example the structure below is described as 3-pyridyl with the X ¹ substituent in the ortho position, the X ² substituent in the meta position, and X ³ substituent in the para position:

To provide a more concise description, some of the quantitative expressions given herein are not qualified with the term "about". It is understood that, whether the term "about" is used explicitly or not, every quantity given herein is meant to refer to the actual given value, and it is also meant to refer to the approximation to such given value that would reasonably be inferred based on the ordinary skill in the art, including equivalents and approximations due to the experimental and/or measurement conditions for such given value. Whenever a yield is given as a percentage, such yield refers to a mass of the entity for which the yield is given with respect to the maximum amount of the same entity that could be obtained under the particular stoichiometric conditions. Concentrations that are given as percentages refer to mass ratios, unless indicated differently.

The terms "buffered" solution or "buffer" solution are used herein interchangeably according to their standard meaning. Buffered solutions are used to control the pH of a medium, and their choice, use, and function is known to those of ordinary skill in the art. See, for example, G.D. Considine, ed., Van Nostrand's Encyclopedia of Chemistry, p. 261 , 5 ^th ed. (2005), describing, inter alia, buffer solutions and how the concentrations of the buffer constituents relate to the pH of the buffer. For example, a buffered solution is obtained by adding gS0 ₄ and NaHCOs to a solution in a 10: 1 w/w ratio to maintain the pH of the solution at about 7.5.

Any formula given herein is intended to represent compounds having structures depicted by the structural formula as well as certain variations or forms. In particular, compounds of any formula given herein may have asymmetric centers and therefore exist in different enantiomeric forms. Ail optica! isomers of the compounds of the general formula, and mixtures thereof, are considered within the scope of the formula. Thus, any formula given herein is intended to represent a racemate, one or more enantiomeric forms, one or more diastereomeric forms, one or more atropisomeric forms, and mixtures thereof. Furthermore, certain structures may exist as geometric isomers (i.e., cis and trans isomers), as tautomers, or as atropisomers.

It is also to be understood that compounds that have the same molecular formula but differ in the nature or sequence of bonding of their atoms or the arrangement of their atoms in space are termed "isomers." Isomers that differ in the arrangement of their atoms in space are termed "."

Stereoisomers that are not mirror images of one another are termed "diastereomers" and those that are non-superimposab!e mirror images of each other are termed "enantiomers." When a compound has an asymmetric center, for example, it is bonded to four different groups, and a pair of enantiomers is possible. An enantiomer can be characterized by the absolute configuration of its asymmetric center and is described by the R-and S- sequencing rules of Cahn and Prelog, or by the manner in which the molecule rotates the plane of polarized light and designated as dextrorotatory or levorotatory (i.e., as (+)- or (-)-isomers respectively). A chirai compound can exist as either an individual enantiomer or as a mixture thereof. A mixture containing equal proportions of the enantiomers is called a "racemic mixture."

"Tautomers" refer to compounds that are interchangeable forms of a particular compound structure, and that vary in the displacement of hydrogen atoms and electrons. Thus, two structures may be in equilibrium through the movement of π electrons and an atom (usually H). For example, enols and ketones are tautomers because they are rapidly interconverted by treatment with either acid or base. Another example of tautomerism is the aci-and nitro- forms of phenyl nitromethane, thai are likewise formed by treatment with acid or base.

Tautomeric forms may be relevant to the attainment of the optimal chemical reactivity and biological activity of a compound of interest.

The compounds of this invention may possess one or more asymmetric centers; such compounds can therefore be produced as individual (R)- or (S)~ stereoisomers or as mixtures thereof.

Unless indicated otherwise, the description or naming of a particular compound in the specification and claims is intended to include both individual enantiomers and mixtures, racemic or otherwise, thereof. The methods for the determination of stereochemistry and the separation of stereoisomers are well-known in the art.

Certain examples contain chemical structures that are depicted as an absolute enantiomer but are intended to indicate enatiopure material that is of unknown configuration. In these cases (R*) or (S*) is used in the name to indicate that the absolute stereochemistry of the corresponding stereocenter is unknown. Thus, a compound designated as (R*) refers to an enantiopure compound with an absolute configuration of either (R) or (S). In cases where the absolute stereochemistry has been confirmed, the structures are named using (R) and (S).

The symbols and ^mmmm are used as meaning the same spatial arrangement in chemical structures shown herein. Analogously, the symbols and are used as meaning the same spatial arrangement in chemical structures shown herein.

Additionally, any formula given herein is intended to refer also to hydrates, solvates, and polymorphs of such compounds, and mixtures thereof, even if such forms are not listed explicitly. Certain compounds of Formula (I) (as well as Formulas (II), (IIA), (IIB), (III), (IV), (V), and (VI)), or pharmaceutically acceptable salts of compounds of Formula (I) (as well as Formulas (II), (IIA), (IIB), (III), (IV), (V), and (VI)) may be obtained as solvates. Solvates include those formed from the interaction or compiexation of compounds of the invention with one or more solvents, either in solution or as a solid or crystalline form. In some embodiments, the solvent is water andthe solvates are hydrates. In addition, certain crystalline forms of compounds of Formula (I) (as well as Formulas (II), (IIA), (MB), (III), (IV), (V), and (VI)) or pharmaceutically acceptable salts of compounds of Formula (I) (as well as Formulas (II), (IIA), (MB), (III), (IV), (V), and (VI)) may be obtained as co~ crystals. In certain embodiments of the invention, compounds of Formula (I) were obtained in a crystalline form. In other embodiments, crystalline forms of compounds of Formula (!) were cubic in nature. In other embodiments, pharmaceutically acceptable salts of compounds of Formula (I) were obtained in a crystalline form. In still other embodiments, compounds of Formula (I) were obtained in one of several polymorphic forms, as a mixture of crystalline forms, as a polymorphic form, or as an amorphous form. In other

embodiments, compounds of Formula (I) convert in solution between one or more crystalline forms and/or polymorphic forms.

Reference to a compound herein stands for a reference to any one of: (a) the actually recited form of such compound, and (b) any of the forms of such compound in the medium in which the compound is being considered when named. For example, reference herein to a compound such as R- COOH, encompasses reference to any one of, for example, R-COOH _(S) , R- COOH( _S oi), and R-COO ^" ( _S oi). In this example, R-COOH _(S ) refers to the solid compound, as it could be for example in a tablet or some other solid pharmaceutical composition or preparation; R-COOH _{SO !) refers to the undissociated form of the compound in a solvent; and R-COO ^" ( _SO n refers to the dissociated form of the compound in a solvent, such as the dissociated form of the compound in an aqueous environment, whether such dissociated form derives from R-COOH, from a salt thereof, or from any other entity that yields R-COO ^" upon dissociation in the medium being considered. In another example, an expression such as "exposing an entity to compound of formula R-COOH" refers to the exposure of such entity to the form, or forms, of the compound R-COOH that exists, or exist, in the medium in which such exposure takes place. In still another example, an expression such as

"reacting an entity with a compound of formula R-COOH" refers to the reacting of (a) such entity in the chemically relevant form, or forms, of such entity that exists, or exist, in the medium in which such reacting takes place, with (b) the chemically relevant form, or forms, of the compound R-COOH that exists, or exist, in the medium in which such reacting takes place. In this regard, if such entity is for example in an aqueous environment, it is

understood that the compound R-COOH is in such same medium, and therefore the entity is being exposed to species such as R-COOH _(aq) and/or R- COO ^' (aq), where the subscript "(aq)" stands for "aqueous ^" according to its conventional meaning in chemistry and biochemistry. A carboxyiic acid functional group has been chosen in these nomenclature examples; this choice is not intended, however, as a limitation but it is merely an illustration. It is understood that analogous examples can be provided in terms of other functional groups, including but not limited to hydroxyl, basic nitrogen members, such as those in amines, and any other group that interacts or transforms according to known manners in the medium that contains the compound. Such interactions and transformations include, but are not limited to, dissociation, association, tautomerism, solvolysis, including hydrolysis, solvation, including hydration, protonation, and deprotonation. No further examples in this regard are provided herein because these interactions and transformations in a given medium are known by any one of ordinary skill in the art.

In another example, a zwitterionic compound is encompassed herein by referring to a compound that is known to form a zwitterion, even if it is not explicitly named in its zwitterionic form. Terms such as zwitterion, zwitterions, and their synonyms zwitterionic compound(s) are standard lUPAC-endorsed names that are well known and part of standard sets of defined scientific names. In this regard, the name zwitterion is assigned the name identification CHEBI:27369 by the Chemical Entities of Biological Interest (ChEBI) dictionary of molecular entities. As generally well known, a zwitterion or zwitterionic compound is a neutral compound that has formal unit charges of opposite sign. Sometimes these compounds are referred to by the term "inner salts". Other sources refer to these compounds as "dipolar ions", although the latter term is regarded by still other sources as a misnomer. As a specific example, aminoethanoic acid (the amino acid glycine) has the formula H ₂ NCH ₂ COOH, and it exists in some media (in this case in neutral media) in the form of the zwitterion ⁺ H ₃ NCH ₂ COO ^" . Zwitterions, zwitterionic compounds, inner salts and dipolar ions in the known and well established meanings of these terms are within the scope of this invention, as would in any case be so appreciated by those of ordinary skill in the art. Because there is no need to name each and every embodiment that would be recognized by those of ordinary skill in the art, no structures of the zwitterionic compounds that are associated with the compounds of this invention are given explicitly herein. They are, however, part of the embodiments of this invention. No further examples in this regard are provided herein because the interactions and transformations in a given medium that lead to the various forms of a given compound are known by any one of ordinary skill in the art.

Any formula given herein is also intended to represent unlabeled forms as well as isotopicaiiy labeled forms of the compounds. Isotopicaiiy labeled compounds have structures depicted by the formulas given herein except that one or more atoms are replaced by an atom having a selected atomic mass or mass number. Examples of isotopes that can be incorporated into

compounds of the invention include isotopes of hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, chlorine, and iodine such as ² H, ³ H, ¹ C, ¹³ C, ¹⁴ C, ¹⁵ N, ¹⁸ 0, ¹⁷ 0, ³¹ P, ³² P, ³⁵ S, ¹⁸ F, ³⁶ Ci, ⁵ i, respectively. Such isotopicaiiy labeled compounds are useful in metabolic studies (preferably with ⁴ C), reaction kinetic studies (with, for example H or ^ύ ), detection or imaging techniques [such as positron emission tomography (PET) or single- photon emission computed tomography (SPECT)] including drug or substrate tissue distribution assays, or in radioactive treatment of patients. In particular, an ' ⁸ F or ¹¹ C labeled compound may be particularly preferred for PET or

SPECT studies. Further, substitution with heavier isotopes such as deuterium (i.e. , ² H) may afford certain therapeutic advantages resulting from greater metabolic stability, for example increased in vivo half-life or reduced dosage requirements. Isotopicaiiy labeled compounds of this invention and prodrugs thereof can generally be prepared by carrying out the procedures disclosed in the schemes or in the examples and preparations described below by substituting a readily available isotopicaiiy labeled reagent for a non- isotopicaily labeled reagent. When referring to any formula given herein, the selection of a particular moiety from a list of possible species for a specified variable is not intended to define the same choice of the species for the variable appearing elsewhere. In other words, where a variable appears more than once, the choice of the species from a specified list is independent of the choice of the species for the same variable elsewhere in the formula, unless stated otherwise.

According to the foregoing interpretive considerations on assignments and nomenclature, it is understood that explicit reference herein to a set implies, where chemically meaningful and unless indicated otherwise, independent reference to embodiments of such set, and reference to each and every one of the possible embodiments of subsets of the set referred to explicitly.

By way of a first example on substituent terminology, if substituent S example is one of Si and S2, and substituent S ² _exa mpie is one of S3 and S ₄ , then these assignments refer to embodiments of this invention given according to the Choices S example is Si and S example is S3; S example IS Si and S example IS S ₄ J S example IS S2 and S example IS S3, S example IS S2 and S example IS S4, and equivalents of each one of such choices. The shorter terminology "S ¹ example is one of S and S2, and S ² _eX ampie is one of S3 and S ₄ " is accordingly used herein for the sake of brevity, but not by way of limitation. The foregoing first example on substituent terminology, which is stated in generic terms, is meant to illustrate the various substituent assignments described herein. The foregoing convention given herein for substituents extends, when applicable, to members such as R ¹ , R ² R ^2a , R ^2b , R ^2c , R ^2d , R ^2e , R ^2f , R ³ , R ^3a , R ³ , R ^3c , R ^3d , R ^3e , R ^3e1 , R ⁴ , Het ¹ , and Hal ² , and any other generic substituent symbol used herein.

Furthermore, when more than one assignment is given for any member or substituent, embodiments of this invention comprise the various groupings that can be made from the listed assignments, taken independently, and equivalents thereof. By way of a second example on substituent terminology, if it is herein described that substituent S _exa mpie s one of Si , S2, and S3, this listing refers to embodiments of this invention for which Sexampie is Si ; Sexampie is S2; Sexa pie is S3; S _exa mpie is one of Si and S2; Sexa ie is one of Si and S3; Sexamp!e is one of S2 and S3; Sexampie is one of Si , S2 and S3; and Sexampie is any equivalent of each one of these choices. The shorter terminology "Sexampie is one of Si , 82, and S3" is accordingly used herein for the sake of brevity, but not by way of limitation. The foregoing second example on substituent terminology, which is stated in generic terms, is meant to illustrate the various substituent assignments described herein. The foregoing convention given herein for substituents extends, when applicable, to members such as as R ¹ , R ² , R ^2a , R ^2b , R ^2c , R ^d , R ^2e , R ^2f , R ³ , R ^3a , R ³ , R ^3c , R ^3d , R ^3e , R ^3e1 , R ⁴ Het ¹ , and Hal ² , and any other generic substituent symbol used herein.

The nomenclature "C . with j > i, when applied herein to a class of substituents, is meant to refer to embodiments of this invention for which each and every one of the number of carbon members, from i to j including i and j, is independently realized. By way of example, the term C1-3 refers

independently to embodiments that have one carbon member (C-i ), embodiments that have two carbon members (C2), and embodiments that have three carbon members (C ₃ ).

The term G _n -maikyl refers to an aliphatic chain, whether straight or branched, with a total number N of carbon members in the chain that satisfies n < N < m, with m > n. Any disubstituent referred to herein is meant to encompass the various attachment possibilities when more than one of such possibilities are allowed. For example, reference to disubstituent -A-B-, where A≠ B, refers herein to such disubstituent with A attached to a first substituted member and B attached to a second substituted member, and it also refers to such disubstituent with A attached to the second substituted member and B attached to the first substituted member.

The invention includes also pharmaceutically acceptable salts of the compounds of Formula (I) (as well as Formulas (II), (IIA), (MB), (III), (IV), (V), and (VI)), preferably of those described above and of the specific compounds exemplified herein, and methods of treatment using such salts.

The term "pharmaceutically acceptable" means approved or approvable by a regulatory agency of Federal or a state government or the corresponding agency in countries other than the United States, or that is listed in the U, S. Pharmcopoeia or other generally recognized pharmacopoeia for use in animals, and more particularly, in humans.

A "pharmaceutically acceptable salt" is intended to mean a salt of a free acid or base of compounds represented by Formula (I) (as well as Formulas (II), (MA), (MB), (III), (IV), (V), and (VI)) that are non-toxic, biologically tolerable, or otherwise biologically suitable for administration to the subject. It should possess the desired pharmacological activity of the parent compound. See, generally, G.S. Pauiekuhn, et al., "Trends in Active Pharmaceutical Ingredient Salt Selection based on Analysis of the Orange Book Database", J. Med. Chem., 2007, 50:6665-72, S.M. Berge, et al., "Pharmaceutical Salts", J Pharm Sci., 1977, 66: 1 -19, and Handbook of Pharmaceutical Salts,

Properties, Selection, and Use, Stahi and Wermuth, Eds., Wiley-VCH and VHCA, Zurich, 2002. Examples of pharmaceutically acceptable salts are those that are pharmacologically effective and suitable for contact with the tissues of patients without undue toxicity, irritation, or allergic response. A compound of Formula (I) (as well as Formulas (II), (IIA), (MB), (III), (IV), (V), and (VI)) may possess a sufficiently acidic group, a sufficiently basic group, or both types of functional groups, and accordingly react with a number of inorganic or organic bases, and inorganic and organic acids, to form a pharmaceutically acceptable salt.

Examples of pharmaceutically acceptable salts include sulfates, pyrosuifates, bisuifates, sulfites, bisulfites, phosphates, monohydrogen- phosphates, dihydrogenphosphates, metaphosphates, pyrophosphates, chlorides, bromides, iodides, acetates, propionates, decanoates, capryiates, acryiates, formates, isobutyrates, caproates, heptanoates, propiolates, oxalates, maionates, succinates, suberates, sebacates, fumarates, maieates, butyne-1 ,4-dioates, hexyne-1 ,6-dioates, benzoates, chlorobenzoates, methylbenzoates, dinitrobenzoates, hydroxybenzoates, methoxybenzoates, phthaiates, sulfonates, xylenesulfonates, phenyiacetates, phenyipropionates, phenylbutyrates, citrates, lactates, γ-hydroxybutyrates, glycolates, tartrates, methane-sulfonates, propanesuifonates, naphthaiene-1 -sulfonates, naphthaiene-2-suifonates, and mandeiates. When the compounds of Formula (I) (as well as Formulas (II), (l!A), (MB), (III), (IV), (V), and (VI)) contain a basic nitrogen, the desired

pharmaceutically acceptable salt may be prepared by any suitable method available in the art. For example, treatment of the free base with an inorganic acid, such as hydrochloric acid, hydrobromic acid, sulfuric acid, sulfamic acid, nitric acid, boric acid, phosphoric acid, and the like, or with an organic acid, such as acetic acid, phenyiacetic acid, propionic acid, stearic acid, lactic acid, ascorbic acid, maleic acid, hydroxymaieic acid, isethionic acid, succinic acid, valeric acid, fumaric acid, malonic acid, pyruvic acid, oxalic acid, glycoiic acid, salicylic acid, oleic acid, palmitic acid, lauric acid, a pyranosidyl acid, such as glucuronic acid or gaiacturonic acid, an aipha-hydroxy acid, such as mandelic acid, citric acid, or tartaric acid, an amino acid, such as aspartic acid, glutaric acid or glutamic acid, an aromatic acid, such as benzoic acid, 2~

acetoxybenzoic acid, naphthoic acid, or cinnamic acid, a sulfonic acid, such as laurylsulfonic acid, p-toluenesulfonic acid, methanesulfonic acid,

ethanesuifonic acid, any compatible mixture of acids such as those given as examples herein, and any other acid and mixture thereof that are regarded as equivalents or acceptable substitutes in light of the ordinary level of skill in this technology.

When the compound of Formula (I) (as well as Formulas (II), (MA),

(MB), (III), (IV), (V), and (VI)) is an acid, such as a carboxyiic acid or sulfonic acid, the desired pharmaceutically acceptable salt may be prepared by any suitable method, for example, treatment of the free acid with an inorganic or organic base, such as an amine (primary, secondary or tertiary), an alkali metal hydroxide, alkaline earth metal hydroxide, any compatible mixture of bases such as those given as examples herein, and any other base and mixture thereof that are regarded as equivalents or acceptable substitutes in light of the ordinary level of skill in this technology. Illustrative examples of suitable salts include organic salts derived from amino acids, such as N- methyl-D-glucamine, lysine, choline, glycine and arginine, ammonia, carbonates, bicarbonates, primary, secondary, and tertiary amines, and cyclic amines, such as tromethamine, benzylamines, pyrrolidines, piperidine, morphoiine, and piperazine, and inorganic salts derived from sodium, calcium, potassium, magnesium, manganese, iron, copper, zinc, aluminum, and lithium.

The invention also relates to pharmaceutically acceptable prodrugs of the compounds of Formula (I) (as well as Formulas (II), (ΠΑ), (MB), (III), (!V), (V), and (VI)), and treatment methods employing such pharmaceutically acceptable prodrugs. The term "prodrug" means a precursor of a designated compound that, following administration to a subject, yields the compound in vivo via a chemical or physiological process such as solvolysis or enzymatic cleavage, or under physiological conditions (e.g., a prodrug on being brought to physiological pH is converted to the compound of Formula (I). A

"pharmaceutically acceptable prodrug" is a prodrug that is non-toxic, biologically tolerable, and otherwise biologically suitable for administration to the subject. Illustrative procedures for the selection and preparation of suitable prodrug derivatives are described, for example, in "Design of Prodrugs", ed. H. Bundgaard, Elsevier, 1985.

Exemplary prodrugs include compounds having an amino acid residue, or a polypeptide chain of two or more (e.g. , two, three or four) amino acid residues, covalently joined through an amide or ester bond to a free amino, hydroxy!, or carboxylic acid group of a compound of Formula (I) (as well as Formulas (II), (MA), (MB), (III), (IV), (V), and (VI)). Examples of amino acid residues include the twenty naturally occurring amino acids, commonly designated by three letter symbols, as well as 4-hydroxyproiine,

hydroxylysine, demosine, isodemosine, 3-methylhistidine, norvalin, beta- alanine, gamma-aminobutyric acid, citruiiine homocysteine, homoserine, ornithine and methionine suifone.

Additional types of prodrugs may be produced, for instance, by derivatizing free carboxyi groups of structures of Formula (I) (as well as Formulas (II), ( A), (MB), ( l), (IV), (V), and (VI)) as amides or alkyi esters. Examples of amides include those derived from ammonia, primary d-ealkyl amines and secondary di(C -ealkyl) amines. Secondary amines include 5- or 6-membered heterocycioalkyi or heteroaryl ring moieties. Examples of amides include those that are derived from ammonia, Ci- ₃ alkyl primary amines, and di(Ci _-2 aiky!)amines. Examples of esters of the invention include Ci-7alkyl, Cs-rcycloalkyl, phenyl, and phenyl(Ci-6alkyl) esters. Preferred esters include methyl esters. Prodrugs may also be prepared by derivatizing free hydroxy groups using groups including hemisuccinates, phosphate esters, dimethylaminoacetates, and phosphoryloxymethyloxycarbonyls, following procedures such as those outlined in Fieisher et a!., Adv. Drug Delivery Rev. 1996, 19, 1 15-130. Carbamate derivatives of hydroxy and amino groups may also yield prodrugs. Carbonate derivatives, sulfonate esters, and sulfate esters of hydroxy groups may also provide prodrugs. Derivatization of hydroxy groups as (acyloxy)methyi and (acyloxy)ethyl ethers, wherein the acyl group may be an alkyi ester, optionally substituted with one or more ether, amine, or carboxylic acid functionalities, or where the acyl group is an amino acid ester as described above, is also useful to yield prodrugs. Prodrugs of this type may be prepared as described in Robinson et ai., J Med Chem.

1996, 39 (1 ), 10-18. Free amines can also be derivatized as amides, sulfonamides or phosphonamides. Ail of these prodrug moieties may incorporate groups including ether, amine, and carboxylic acid functionalities.

The present invention also relates to pharmaceutically active

metabolites of the compounds of Formula (!) (as well as Formulas (II), (l!A), (MB), (III), (IV), (V), and (VI)), which may also be used in the methods of the invention. A "pharmaceutically active metabolite" means a pharmacologically active product of metabolism in the body of a compound of Formula (I) (as well as Formulas (II), (MA), (MB), (III), (IV), (V), and (VI) as applicable) or salt thereof. Prodrugs and active metabolites of a compound may be determined using routine techniques known or available in the art. See, e.g., Bertolini, et al., J Med Chem. 1997, 40, 201 1 -2016; Shan, et al., J Pharm Sci. 1997, 86 (7), 765-767; Bagshawe, Drug Dev Res. 1995, 34, 220-230; Bodor, Adv Drug Res. 1984, 13, 224-331 ; Bundgaard, Design of Prodrugs (Elsevier Press, 1985); and Larsen, Design and Application of Prodrugs, Drug Design and Development (Krogsgaard-Larsen, et al., eds., Harwood Academic

Publishers, 1991).

The compounds of Formula (!) (as well as Formulas (II), (MA), (MB), (Ml), (IV), (V), and (VI)) and their pharmaceutically acceptable salts,

pharmaceutically acceptable prodrugs, and pharmaceutically active metabolites of the present invention are useful as modulators of the NR2B receptor in the methods of the invention. As such modulators, the compounds may act as antagonists, agonists, or inverse agonists. The term "modulators" include both inhibitors and activators, where "inhibitors" refer to compounds that decrease, prevent, inactivate, desensitize, or down-regulate the NR2B receptor expression or activity, and "activators" are compounds that increase, activate, facilitate, sensitize, or up-regulate NR2B receptor expression or activity.

The term "treat", "treatment" or "treating", as used herein, is intended to refer to administration of an active agent or composition of the invention to a subject for the purpose of affecting a therapeutic or prophylactic benefit through modulation of NR2B receptor activity. Treating includes reversing, ameliorating, alleviating, inhibiting the progress of, lessening the severity of, or preventing a disease, disorder, or condition, or one or more symptoms of such disease, disorder or condition mediated through modulation of IMR2B receptor activity. The term "subject" refers to a mammalian patient in need of such treatment, such as a human.

Accordingly, the invention relates to methods of using the compounds described herein to treat subjects diagnosed with or suffering from a disease, disorder, or condition mediated by NR2B receptor activity, such as: bipolar disorder I depressed, hypomanic, manic and mixed form; bipolar disorder II; depressive disorders, such as single depressive episode or recurrent major depressive disorder, minor depressive disorder, treatment-resistant depression, depressive disorder with postpartum onset, disruptive mood dysregulation disorder, depressive disorders with psychotic symptoms;

persistent mood disorders, such as cyclothymia, dysthymia, euthymia; and premenstrual dysphoric disorder; anxiety disorders, general anxiety disorder, panic disorder with or without agoraphobia, specific phobia, social anxiety disorder, chronic anxiety disorders; obsessive compulsive disorder; reaction to sever stress and adjustment disorders, such as post traumatic stress disorder (PTSD); other neurotic disorders such as depersonaiisation- derealisation syndrome; pervasive developmental disorders, including but not limited to Asperger's syndrome and Rett's syndrome, autistic disorders, childhood autism and overactive disorder associated with mental retardation and stereotyped movements, specific developmental disorder of motor function, specific developmental disorders of scholastic skills; postnatal (postpartum) and prenatal depression; eating disorders, including but not limited to anorexia nervosa, bulimia nervosa, pica and binge eating disorder; Parkinson's disease; second Parkinsonism, such as postencephalitic

Parkinsonism; Parkinsonism comprised in other disorders; Lewis body disease; degenerative diseases of the basal ganglia; other extrapyramidal and movement disorders including but not limited to tremor, essential tremor and drug-induced tremor, myoclonus, chorea and drug-induced chorea, drug- induced tics and tics of organic origin, drug-induced acute dystonia, drug- induced tardive dyskinesia, L-dopa-induced dyskinesia; neuroleptic-induced movement disorders including but not limited to neuroleptic malignant syndrome (NMS), neuroleptic induced parkinsonism, neuroleptic-induced early onset or acute dyskinesia, neuroleptic-induced acute dystonia, neuroleptic-induced acute akathisia, neuroleptic-induced tardive dyskinesia, neuroleptic-induced tremor; restless leg syndrome, Stiff-man syndrome;

dystonia including but not limited to focal dystonia, multiple-focal or segmental dystonia, torsion dystonia, hemispheric, generalised and tardive dystonia (induced by psychopharmacoiogica! drugs). Focal dystonia include cervical dystonia (torticoili), blepharospasm (cramp of the eyelid), appendicular dystonia (cramp in the extremities, like the writer's cramp), oromandibular dystonia and spasmodic dysphonia (cramp of the vocal cord); epilepsy, including localization-related (focal)(partial) idiopathic epilepsy and epileptic syndromes with seizures of localized onset, localization-related (focal)(partiai) symptomatic epilepsy and epileptic syndromes with simple partial seizures, localization-related (focai)(partial) symptomatic epilepsy and epileptic syndromes with complex partial seizures, generalized idiopathic epilepsy and epileptic syndromes including but not limited to myoclonic epilepsy in infancy, neonatal convulsions (familial), childhood absence epilepsy (pyknolepsy), epilepsy with grand mal seizures on awakening, absence epilepsy, myoclonic epilepsy (impulsive petit mal) and nonspecific atonic, clonic, myoclonic, tonic, tonic-clonic epileptic seizures; epilepsy with myoclonic absences, myoclonic- astatic seizures, infantile spasms, Lennox-Gastaut syndrome, Salaam attacks, symptomatic early myoclonic encephalopathy, West's syndrome, petit and grand mal seizures; status epiiepticus; persistent somatoform disorders; acute, chronic and chronic intractable pain, headache; acute and chronic pain related to physiological processes and physical disorders including but not limited to back pain, tooth pain, abdominal pain, low back pain, pain in joints; acute and chronic pain that is related to diseases of the musculoskeletal system and connective tissue including, but not limited to rheumatism, myalgia, neuralgia and fibromyalgia; acute and chronic pain that is related to nerve, nerve root and plexus disorders, such as trigeminal pain, postzoster neuralgia, phantom limb syndrome with pain, carpal tunnel syndrome, lesion of sciatic nerve, diabetic mononeuropathy; acute and chronic pain that is related to polyneuropathies and other disorders of the peripheral nervous system, such as hereditary and idiopathic neuropathy, inflammatory polyneuropathy, polyneuropathy induced by drugs, alcohol or toxic agents, polyneuropathy in neoplastic disease, diabetic polyneuropathy; and acute neurodegeneration, such as intracranial brain injuries, such as stroke, diffuse and local brain injuries, epidural, subdural and subarachnoid haemorrhage, and chronic neurodegeneration, such as Alzheimer's disease, Huntington's disease, multiple sclerosis, and ALS; subarachnoid haemorrhage,

intracerebral haemorrhage and other nontraumatic intracranial haemorrhage, cerebral infarction, stroke, occlusion and stenosis or precerebrai and cerebral arteries, not resulting in cerebral infarction, dissection of cerebral arteries, cerebral aneurysm, cerebral atherosclerosis, progressive vascular

leukoencephalopathy, hypertensive encephalopathy, nonpyogenic thrombosis of intracranial venous system, cerebral arteritis, cerebral amyloid angiopathy and sequelae of cerebrovascular diseases; glaucoma and other neuopathies; dementias, vascular demensia, Lewy body dementia, frontotemporal dementia, and HIV-dementia; vertigo and nystagmus; tinnitus;

neuropsychiatric systemic lupus erythematosus; disruptive mood

dysregulation disorder; schizophrenia spectrum disorder; and sleep/wake disorders. In treatment methods according to the invention, an effective amount of a pharmaceutical agent according to the invention is administered to a subject suffering from or diagnosed as having such a disease, disorder, or condition. An "effective amount" means an amount or dose sufficient to generally bring about the desired therapeutic or prophylactic benefit in patients in need of such treatment for the designated disease, disorder, or condition. Effective amounts or doses of the compounds of the present invention may be ascertained by routine methods such as modeling, dose escalation studies or clinical trials, and by taking into consideration routine factors, e.g., the mode or route of administration or drug delivery, the pharmacokinetics of the compound, the severity and course of the disease, disorder, or condition, the subject's previous or ongoing therapy, the subject's health status and response to drugs, and the judgment of the treating physician. An example of a dose is in the range of from about 0.001 to about 200 mg of compound per kg of subject's body weight per day, preferably about 0.05 to 100 mg/kg/day, or about 1 to 35 mg/kg/day, in single or divided dosage units (e.g., BID, TID, QID). For a 70-kg human, an illustrative range for a suitable dosage amount is from about 0.05 to about 7 g/day, or about 0.2 to about 2.5 g/day.

Once improvement of the patient's disease, disorder, or condition has occurred, the dose may be adjusted for preventative or maintenance treatment. For example, the dosage or the frequency of administration, or both, may be reduced as a function of the symptoms, to a level at which the desired therapeutic or prophylactic effect is maintained. Of course, if symptoms have been alleviated to an appropriate level, treatment may cease. Patients may, however, require intermittent treatment on a long-term basis upon any recurrence of symptoms.

In addition, the active agents of the invention may be used in

combination with additional active ingredients in the treatment of the above conditions. The additional active ingredients may be co-administered separately with an active agent of compounds of Table 1 or included with such an agent in a pharmaceutical composition according to the invention, !n an exemplary embodiment, additional active ingredients are those that are known or discovered to be effective in the treatment of conditions, disorders, or diseases mediated by NR2B activity, such as another NR2B modulator or a compound active against another target associated with the particular condition, disorder, or disease. The combination may serve to increase efficacy (e.g., by including in the combination a compound potentiating the potency or effectiveness of an active agent according to the invention), decrease one or more side effects, or decrease the required dose of the active agent according to the invention.

The active agents of the invention are used, alone or in combination with one or more additional active ingredients, to formulate pharmaceutical compositions of the invention. A pharmaceutical composition of the invention comprises: (a) an effective amount of at least one active agent in accordance with the invention; and (b) a pharmaceutically acceptable excipient.

A "pharmaceutically acceptable excipient" refers to a substance that is non-toxic, biologically tolerable, and otherwise biologically suitable for administration to a subject, such as an inert substance, added to a

pharmacological composition or otherwise used as a vehicle, carrier, or diluent to facilitate administration of an agent and that is compatible therewith. Examples of excipients include calcium carbonate, calcium phosphate, various sugars and types of starch, cellulose derivatives, gelatin, vegetable oils, and polyethylene glycols.

Delivery forms of the pharmaceutical compositions containing one or more dosage units of the active agents may be prepared using suitable pharmaceutical excipients and compounding techniques known or that become available to those skilled in the art. The compositions may be administered in the inventive methods by a suitable route of delivery, e.g., oral, parenteral, rectal, topical, or ocular routes, or by inhalation.

The preparation may be in the form of tablets, capsules, sachets, dragees, powders, granules, lozenges, powders for reconstitution, liquid preparations, or suppositories. Preferably, the compositions are formulated for intravenous infusion, topical administration, or oral administration.

For oral administration, the compounds of the invention can be provided in the form of tablets or capsules, or as a solution, emulsion, or suspension. To prepare the oral compositions, the compounds may be formulated to yield a dosage of, e.g., from about 0,05 to about 100 mg/kg daily, or from about 0.05 to about 35 mg/kg daily, or from about 0.1 to about 10 mg/kg daily. For example, a total daily dosage of about 5 mg to 5 g daily may be accomplished by dosing once, twice, three, or four times per day.

Oral tablets may include a compound according to the invention mixed with pharmaceutically acceptable excipients such as inert diluents,

disintegrating agents, binding agents, lubricating agents, sweetening agents, flavoring agents, coloring agents and preservative agents. Suitable inert fillers include sodium and calcium carbonate, sodium and calcium phosphate, lactose, starch, sugar, glucose, methyl cellulose, magnesium sfearate, mannitol, sorbitol, and the like. Exemplary liquid oral excipients include ethanol, glycerol, water, and the like. Starch, polyvinyl-pyrrolidone (PVP), sodium starch giycoiate, microcrystailine cellulose, and alginic acid are suitable disintegrating agents. Binding agents may include starch and gelatin. The lubricating agent, if present, may be magnesium stearate, stearic acid or talc. If desired, the tablets may be coated with a material such as glyceryl monostearate or glyceryl distearate to delay absorption in the gastrointestinal tract, or may be coated with an enteric coating.

Capsules for oral administration include hard and soft gelatin capsules. To prepare hard gelatin capsules, compounds of the invention may be mixed with a solid, semi-solid, or liquid diluent. Soft gelatin capsules may be prepared by mixing the compound of the invention with water, an oil such as peanut oil or olive oil, liquid paraffin, a mixture of mono and di-giycerides of short chain fatty acids, polyethylene glycol 400, or propylene glycol.

Liquids for oral administration may be in the form of suspensions, solutions, emulsions or syrups or may be lyophilized or presented as a dry product for reconstitution with water or other suitable vehicle before use.

Such liquid compositions may optionally contain: pharmaceutically- acceptable excipients such as suspending agents (for example, sorbitol, methyl cellulose, sodium alginate, gelatin, hydroxyefhyiceilulose,

carboxymethylceliulose, aluminum stearate gel and the like); non-aqueous vehicles, e.g., oil (for example, almond oil or fractionated coconut oil), propylene glycol, ethyl alcohol, or water; preservatives (for example, methyl or propyl p-hydroxybenzoate or sorbic acid); wetting agents such as lecithin; and, if desired, flavoring or coloring agents.

The active agents of this invention may also be administered by non- oral routes. For example, the compositions may be formulated for rectal administration as a suppository. For parenteral use, including intravenous, intramuscular, intraperitoneal, or subcutaneous routes, the compounds of the invention may be provided in sterile aqueous solutions or suspensions, buffered to an appropriate pH and isotonicity or in parenteraliy acceptable oil. Suitable aqueous vehicles include Ringer's solution and isotonic sodium chloride. Such forms will be presented in unit-dose form such as ampules or disposable injection devices, in multi-dose forms such as vials from which the appropriate dose may be withdrawn, or in a solid form or pre-concentrate that can be used to prepare an injectable formulation. Illustrative infusion doses may range from about 1 to 1000 g/kg/minute of compound, admixed with a pharmaceutical carrier over a period ranging from several minutes to several days.

For topical administration, the compounds may be mixed with a

pharmaceutical carrier at a concentration of about 0.1 % to about 10% of drug to vehicle. Another mode of administering the compounds of the invention may utilize a patch formulation to affect transdermal delivery.

Compounds of the invention may alternatively be administered in methods of this invention by inhalation, via the nasal or oral routes, e.g., in a spray formulation also containing a suitable carrier.

Exemplary compounds useful in methods of the invention will now be described by reference to the illustrative synthetic schemes for their general preparation below and the specific examples that follow. Artisans will recognize that, to obtain the various compounds herein, starting materials may be suitably selected so that the ultimately desired substituents will be carried through the reaction scheme with or without protection as appropriate to yield the desired product. Alternatively, it may be necessary or desirable to employ, in the place of the ultimately desired substituent, a suitable group that may be carried through the reaction scheme and replaced as appropriate with the desired substituent. Unless otherwise specified, the variables are as defined above in reference to Formula (I). Reactions may be performed between the melting point and the reflux temperature of the solvent, and preferably between 0 °C and the reflux temperature of the solvent. Reactions may be heated employing conventional heating or microwave heating.

Reactions may also be conducted in sealed pressure vessels above the normal reflux temperature of the solvent.

Abbreviations and acronyms used herein include the following

Term Acronym

Diisopropylethylamine DiPEA

4-Dimethylaminopyridine DMAP

1 ,2-Dirnethoxyethane D E

A/,A/-Dimethylformamide DMF

Dimethylsulfoxide DMSO

1 -Ethy!-3-(3- Fnn FRAP nr FilP dimethylaminopropyl)carbodiimide

Diethyl ether Ether, Et ₂ 0

Ethyl Acetate EtOAc, or EA

Ethanol EtOH

Normal-phase silica gel chromatography FCC

Grams g

Hours h

1 -[Bis(dimethylamino)methylene]-1 H-1 ,2,3- triazolo[4,5-b]pyridinium 3-oxid HATU

hexafiuorophosphate

N.N.N'.N'-Tetramethyl-O-i H-benzotriazol-l -

HBTU

yl)uronium hexafiuorophosphate

Hydroxybenzotriazole HOBt

High-pressure liquid chromatography HPLC

Hertz Hz

Isopropyl alcohol /PrOH, IPA Term Acronym

Liquid chromatography and mass

LCMS

spectrometry

Lithium bis(trimethylsilyl)amide LHMDS

Molar M

Mass to charge ratio m/z meta-Chloroperoxybenzoic acid mCPBA

Methyl Iodide Mel

Methanol MeOH

Milligrams mg

Minute min

Milliliter niL

Microliter ML

Millimoles mmol

Mass spectrometry MS

Normal N

N-Bromosuccinimide NBS

N-Chlorosuccinimide NCS

N-lodosuccinimide NiS

Nuclear magnetic resonance NMR

CF ₃ S0 ₃ ^™ or triflate OTf Term Acronym

Palladium(ll)bis(triphenylphosphine) dichloride Pd(PPh ₃ ) ₂ C! ₂

Tetrakis(triphenylphasphine)pailadium(0) Pd(PPh ₃ ) ₄

[1 , 1 '-Bis(di-tert- PdCi _? (dtbpf) or butylphosphino)ferrocene]dichloropalladium(ll) Pd(dtbpf) ₂ CI ₂

Parts per million ppm

Precipitate ppt

Polyietrafiuoroethylene PTFE

Bromotripyrroiidinophosphonium

PyBroP® hexafiuorophosphaie

Retention time t

Room temperature rt

Saturated sat

1 -Chloromethyl-4-fluoro-1 ,4- diazoniabicyclo[2.2.2]octane Seiectfiuor® bis(tetrafiuoroborate)

[2-(Trimethylsilyl)ethoxy]methyl acetal SEM

Supercritical Fluid Chromatography SFC

Temperature T

Tetra-n-butylammonium fluoride TBAF

Triethylamine TEA

Trifluoroacetic acid TFA

Tetrahydrofuran THF T( Θ :!ΓΟΊ Acronym

Thin layer chromatography TLC

PREPARATIVE EXAMPLES

Exemplary compounds useful in methods of the invention will now be described by reference to the illustrative synthetic schemes for their general preparation below and the specific examples to follow.

According to SCHEME 1 , commercially ava liable or synthetically accessible 6-bromo-1 H-pyrrolo[3,2-b]pyridine is halogenated under conditions known to one skilled in the art. For example, 6~bromo-1 H~pyrroio[3,2- bjpyridine is halogenated using a reagent such as NCS, NBS, and like, in a suitable solvent such as DMF, and the like, at a temperature ranging from 0 ^° C to rt, to provide a compound of formula (IX), where R' is CI or Br. A compound of formula (IX), where R ¹ is F, is prepared under fiuorinating conditions known to one skilled in the art, for example, reaction with a fiuorinating agent such as Selectfluor ^® , pyridine, in a suitable solvent such as ACN, and the like, at room temperature.

SCHEME 2

According to SCHEME 2, 2-bronioacetyl chloride is reacted with a commercially available or synthetically accessible suitably substituted heterocycloalkylamine of formula (VII), where A is a fully saturated or partially saturated 3-7 membered ring optionally containing additional S, N, or 0 atoms, or suitably substituted amine of formula (VIII), where R ^3a and R ³ are as defined in Formula (I), in the presence of a suitable base such as Et ₃ N (TEA), in a solvent such as acetonitrile (ACN), at temperatures ranging from - 78 °C to rt, to provide a compound of formula (XII) or (XIII).

SCHEME 3

(XIV)

or

Y Het ¹ ( ^xx )

According to SCHEME 3, a compound of formula (IX), where R ¹ is H, CI, F, is alkylated with a compound of formula (XII), (XIII), (XIV), or (XX) where Y is CI, Br or ~OS0 ₂ IV1e, employing a base such as NaH, in a suitable solvent such as DMF, at temperatures ranging from 0 ^° C to rt, to afford a compound of formula (X). When the alkylating agent is a compound of formula (XIV), R ^3e is OC-i-salkyl, Ci-salkyi or cyclopropyl. When the alkylating agent is a compound of formula (XX), Het ¹ is a suitably substituted heteroary! such as isoxazole, and Y is CI,

A compound of formula (X), where R' is H, is further fiuorinated employing conditions previously described, to provide a compound of formula (X), where R is F.

(IX) (X!)

According to SCHEME 4, a compound of formula (IX), where R ¹ is H, or CI, is reacted in a metal mediated cross coupling reaction to provide a compound of formula (XI), where R ² is an phenyl, pyridiny!, thienyl, each optionally substituted with of one, two or three members independently selected from halo, -CN, C _h alky! and C-i-shaloalkyl. For example, a compound of formula (IX), where R ¹ is H, or CI, is reacted with a suitably substituted aryi or heteroaryl boronic acid, boronate ester, and the like, in the presence of a palladium catalyst such as PdCl2(dtbpf), Pd(PPh ₃ ) ₄ , and the like, a base such as K ₃ P0 ₄ , aq. a ₂ CQ3, CS2CO3, and the like, in a suitable solvent such as 1 ,4-dioxane, DMF, water, or a mixture thereof, at a

temperature ranging from 60 - 90 °C, for a period of about 16 h, to provide a compound of formula (XI),

A compound of formula (XI), where R is H, and R ² is a suitably substituted phenyl, is halogenated, employing conditions known to one skilled in the art, for example, by reaction with NIS, and like, in a suitable solvent such as DMF, and the like, at a temperature ranging from 0 ^° C to rt, to provide a compound of formula (XI), where R ¹ is I.

In a further method, a compound of formula (XI), where R is Br, the N1 nitrogen is protected with a suitable nitrogen protecting group such as SEM, employing conditions known to one skilled in the art. For example, reaction of bromo-6-(4-fiuoro-3-methylphenyi)-1 H-pyrrolo[3,2-b]pyridine with 2- chioromethoxyethyl)trimethyisilane, in the presence of a base such as NaH, and the like, in a suitable solvent such as DMF, at temperatures ranging from 0 ^° C to rt, provides 3-bromo-6-(4-fiuoro-3-methylphenyi)-1 -((2- (trimethyisilyi)ethoxy)methyi)-1 H-pyrrolo[3,2-b]pyridine. Trans-halogenation of a compound where R ¹ is Br, is achieved under reaction conditions such as fBuLi, and N-fiuoro-N-(phenylsuifonyl)benzenesulfonamide, in a solvent such as THF, to provide a compound where R ¹ is F. Subsequent deprotection of the SEM group, under conditions known to one skilled in the art, such as reaction with TBAF, in a suitable solvent such asTHF, at a temperature of about 60 ^° C provides a compound of formula (XI), where R ¹ is F,

SCHEME 5

According to SCHEME 5, commercially available or synthetically accessible 5-bromo-2-chloropyridin-3-amine is coupled with a boronic acid or boronic ester of formula (XVI), where R ² is a suitably substituted phenyl, in the presence of a palladium catalyst such as Pd(dtbpf) ₂ Cl2, and the like, a base such as K3PO4, in a solvent such as dioxane, water, or a mixture thereof, at 80 °C to provide a compound of formula (XVII). A compound of formula (XVII) is reacted in a palladium-catalyzed Sonogashira cross-coupling reaction with a (trimethylsilyl)alkyne, a palladium catalyst such as Pd(PPh ₃ ) ₂ CI ₂ , and the like, a ligand such as PPh ₃ , a copper(l) cocataiyst such as Cul, an amine base such as Et ₃ N, DBU, DIPEA, and the like, CsF, in a solvent such as D F,

Et ₂ 0, dioxane, THF, and the like, at a temperature of about 90 ^° C, to provide a compound of formula (XVIII). Reaction of a compound of formula (XVIII) with a base such as NaH, ethyl 2-bromoacetate, in a suitable solvent such as DMF, and the like, at a temperature ranging from 0 °C to room temperature, for a period of about 12-24 h, provides a compound of formula (VI), where R ¹ is H and R ⁴ is CH ₃ .

SCHEME 6

According to SCHEME 8, a compound of formula (VI), is prepared in two steps from a compound of formula (XI). In a first step, a compound of formula (XI) where R ¹ is H, and R ² is a suitably substituted phenyl or thienyi, is alkylated with electrophile such as ethyl 2-bromoacetate, tert-butyl 2- bromoacetate, and the like, a base such as NaH, and the like, in a suitable solvent such as DMF, a temperatures ranging from 0 ^° C to rt to provide a compound of formula (XXI), where R ^3e is C halky!. Saponification of an ester compound of formula (XXI) under basic conditions such as LiOH, and the like, in a solvent such asTHF and water, at a temperature of about rt, affords a compound of Formula (VI), where R ⁴ is H, and R ^3e is -OH.

A compound of formula (XXI), is prepared from a compound of formula (IX) in two steps. A compound of formula (IX), in a first step is alkylated employing conditions previously described with an electrophile such as ethyl 2-bromoacetate, tert-butyl 2-bromoacetafe, and the like. In a second step, coupling with a suitably substituted phenyl or thienyi boronic acid or ester, employing conditions previously described, provides a compound of formula

It will be understood that in certain instances, in situ ester hydrolysis, without the isolation of a discrete ester (XXI) may occur to provide a compound of Formula (VI), where R^ is -OH,

In an alternate method, a compound of formula (VI) where R ¹ is Ci- ₅ aikyl, R ² is a suitably substituted phenyl, and R ⁴ is H, is prepared from a compound of formula (XXI), wehre R is H, in 3 steps. In a first step, bromination of a compound of formula (XXI), where R is H, employing conditions previously described affords a compound where R ¹ is Br. In a second step, transition-meta! mediated conversion an aryi ha!ide compound where R is Br, employing tetramethyltin, a palladium catalyst such as

Pd(PPh3) ₂ Ci2 _! and the like, an additive such as LiCI, in a suitable solvent such as DMF, ACN, dioxane, xylenes, and the like, at temperatures ranging from SO to 1 10 ^° C affords a compound where R ¹ is CH ₃ , Subsequent deptotection of the ester, employing conditions known to one skilled in the art, for example, reaction with TFA, in a solvent such as DCM, and the like, at temperatures ranging from 0 ^° C to rt, affords a compound of Formula (VI), where R is CH ₃ .

According to SCHEME 7, A compound of Formula (I), where R ¹ and R ⁴ are H or CH3, R ² is a suitably substituted phenyl or thienyl, is prepared by conventional amide bond forming techniques such as coupling reactions which are well known to those skilled in the art. For example, reaction of a suitably substitued heterocycloalkyl amine of formula (XXII) or amine of formula (XXIII) where R ^3a is H or d _-5 alkyl and R ^3b is Ci _-5 alkyl, C _3-6 cycloalkyl, with an acid compound of Formula (VI), where R ^3e is OH, where the acid is activated with an appropriate activating reagent, for example a carbodiimide, such as DCC or EDCI optionally in the presence of HOBt and/or a catalyst such as DMAP; a halotrisaminophosphonium salt such as BOP, or PyBroP; a suitable pyridinium salt such as 2 -chloro-1 -methyl pyridinium chloride; or another suitable coupling agent such as HBTU, HATU, and the like. Coupling reactions are conducted in a suitable solvent such as DCM, THF, DMF and the like, optionally in the presence of a tertiary amine such as N- methylmorpholine, N-ethyldiisopropylamine, or TEA, at a temperature ranging from about 0 °C to rt, to provide compound a of Formula (I).

SCHEME 8

According to SCHEME 8, a compound of formula (XI), where R ¹ and R ^' are H, is reacted with an acid of formula (XXIV), where R ^3ci is cyclobutyl, or Chfe-cyclopropyl, under amide bond forming conditions as previously described, to provide a compound of Formula (V). !n a preferred method, HATU is the coupling reagent, DIPEA is the base, D!VIF is the solvent

SCHEME 9

R ¹

(IX)

According to SCHEME 9, a compound of formula (XI), is reacted with a heteroaryl alkyihalide of formula (XXV), where Hal ² is CI, employing alkyiation conditions previously described to provide a compound of Formula (IV), where R is H or halo, R ² is an suitably substituted phenyl or thienyl, R ^3c is a suitably substituted Cs-ecyc!oaiky!, a suitably substituted 3-6-membered

heterocycioaikyi, or a suitably substituted 5 or 6 membered heteroaryl ring, and R ⁴ is H. In a preferred method the base is NaH, and the solvent is DMF.

In an alternate method, a compound of formula (IX), where R ¹ is H, is alkylated with a heteroaryl alkyihalide of formula (XXV), where Hal ² is CI, then in a second step, reacted in a metal-mediated coupling reaction with a suitably substituted phenyl or thienyl boronic acid or ester, as previously described, to provide a compound of Formula (IV).

SCHEME 10

According to SCHEME 10, a compound of formula (XI), where R is H, and R ² is a suitably substituted phenyl, is reacted with but-3-en-2-one, Au(H!)C , silver trifluoromethanesulfonate, in a solvent such as DCE, at a temperature of about 100 ^° C, to provide compound of Formula (I), where R ³ is CH ₂ CH ₂ (C=0)CH ₃ .

(XI) (')

According to SCHEME 10, a compound of formula (XI), is alkylated under conditions previously described, for example, by reaction with

(chloromethyl)(methyl)sulfane; optionally substituted d-sha!oaikyls such as 1 - bromobutane, l -bromo-3-methyibutane, l -bromo-2-methoxyethane, and the like; (halomethyl)C3-6cycloalkyls such as (bromomethyl)cyclopropane,

(bromomethyl)cyclobutane, and the like; (halomethyl)heterocycloalkyls such as 2~(bromomethyi)oxirane, 3-(bromomethyl)tetrahydrofuran, and the like; 2~ bromo-1 -cyciobutylethanone; 2-bromo-1 -cyclopropylethanone; 2-bromo-1 - phenylethanone; 1 -bromobutan-2-one; (halomethyl)heteroaryls such as 3- (bromomethyl)pyridine, 5-(chioromethyl)-3-methyi-1 ,2,4-oxadiazole, 4- (chioromethyl)-l -methyl-1 H-pyrazole, 4-(chloromethyl)-1 -methyl- H-1 ,2,3- triazole, and the like; 1 -(2-chloroethyl)-1 H-pyrazole; (5-fluoropyrimidin-2- yl)methyl methanesuifonate; or pyrimidin-5-ylmethyl methanesulfonate;

employing aikylation conditions previously described, provides a compound of Formula (I),

A compound of Formula (!), where R ³ is CH ₂ (C™0)Ci-oalkyi, is reduced with a reducing agent such as NaBH ₄ , and the like, in a solvent such as THF, MeOH, or a mixture thereof, at a temperature ranging from ^° C to rt, provides a compound of Formula (I), where R ³ is CH ₂ CH(OH)Ci-5aikyl.

A compound of Formula (I), where R ³ is CH2(C=0)C3-6cycloalkyl, is reacted with a Grignard reagent such as methylmagnesium bromide, and the like, in a suitable solvent such as Et ₂ 0, THF, or a mixture thereof, at a temperature ranging from ^° C to rt, provides a compound of Formula (I), where R ³ is CH ₂ (CH ₃ )(OH) C ₃ . ₆ cycloaikyL

A compound of Formula (I), where R ³ is is reacted with O-methy!hydroxyiamine hydrochloride, a base such as NaHC0 ₃ , and the like, in a suitable solvent such , and the like, provides a

compound of Formula (I), where R ³ is .

A compound of Formula (I), where R ³ is CH ₂ CH(OH)C3.6cycioalkyi is fiuorinated under conditions known to one skilled in the art, for example, reaction with a fiuorinating agent such as DAST, and the like, in a solvent such as DCM, and the like, at a temperature ranging from ^° C to rt, provides a compound of Formula (I), where R ³ is CH ₂ CH(F)C3.6cycioalkyi.

A compound of Formula (I), where R ³ is CH ₂ SCH ₃ , is oxidized under conditions known to one skilled in the art, for example, reaction with an oxidizing agent such as mCPBA, in a solvent such as DCM, and the like, at a temperature ranging from ^° C to rt, provides a compound of Formula (I), where R ³ is CH ₂ (S=0)CH ₃ , and CH ₂ (S0 ₂ )CH ₃ .

Compounds of Formula (I) may be converted to their corresponding salts using methods known to one of ordinary skill in the art. For example, an amine of Formula (I) is treated with trifiuoroacetic acid, HCI, or citric acid in a solvent such as Et ₂ 0, CH ₂ Ci ₂ , THF, MeOH, chloroform, or isopropanoi to provide the corresponding salt form. Alternately, trifiuoroacetic acid or formic acid salts are obtained as a result of reverse phase HPLC purification conditions. Cyrstalline forms of pharmaceutically acceptable salts of compounds of Formula (!) may be obtained in crystalline form by

recrystallization from polar solvents (including mixtures of polar solvents and aqueous mixtures of polar solvents) or from non-polar solvents (including mixtures of non-polar solvents).

Where the compounds according to this invention have at least one chirai center, they may accordingly exist as enantiomers. Where the compounds possess two or more chirai centers, they may additionally exist as diastereomers. It is to be understood that all such isomers and mixtures thereof are encompassed within the scope of the present invention.

Compounds prepared according to the schemes described above may be obtained as single forms, such as single enantiomers, by form-specific synthesis, or by resolution. Compounds prepared according to the schemes above may alternately be obtained as mixtures of various forms, such as racemic (1 : 1 ) or non-racemic (not 1 : 1 ) mixtures. Where racemic and non- racemic mixtures of enantiomers are obtained, single enantiomers may be isolated using conventional separation methods known to one of ordinary skill in the art, such as chirai chromatography, recrystallization, diastereomenc salt formation, derivatization into diastereomenc adducts, biotransformation, or enzymatic transformation. Where regioisomeric or diastereomeric mixtures are obtained, as applicable, single isomers may be separated using

conventional methods such as chromatography or crystallization.

The following specific examples are provided to further illustrate the invention and various preferred embodiments.

EXAMPLES

In obtaining the compounds described in the examples below and the corresponding analytical data, the following experimental and analytical protocols were followed unless otherwise indicated.

Unless otherwise stated, reaction mixtures were magnetically stirred at room temperature (rt) under a nitrogen atmosphere. Where solutions were "dried," they were generally dried over a drying agent such as Na ₂ S04 or MgS0 ₄ . Where mixtures, solutions, and extracts were "concentrated", they were typically concentrated on a rotary evaporator under reduced pressure. Reactions under microwave irradiation conditions were carried out in a Biotage Initiator or CEIV1 (Microwave Reactor) Discover instrument. For the reactions conducted under continuous flow conditions, "flowed through a LTF-VS mixer" refers to the use of a Chemyx Fusion 100 Touch Syringe Pump that is in line via 1/16" PTFE tubing to a LTF-VS mixer (Little Things Factory GmbH (http://www. itf~gmbh.com), unless otherwise indicated.

Normal-phase silica gel chromatography (FCC) was performed on silica gel (Si0 ₂ ) using prepacked cartridges.

Preparative reverse-phase high performance liquid chromatography (RP HPLC) was performed on either:

METHOD A. An Agilent HPLC with an Xterra Prep RP18 column (5 μΜ, 30 x 100 or 50 x 150mm) or an XBridge C18 OBD column (5 μΜ, 30 x 100 or 50 x 150mm), and a mobile phase of 5% ACN in 20m!V1 NH ₄ OH was held for 2 min, then a gradient of 5-99% ACN over 15 min, then held at 99% ACN for 5 min, with a flow rate of 40 or 80 mL/min.

or

METHOD B. A Shimadzu LC-8A Series HPLC with an Inertsii ODS-3 column (3 μιτι, 30 x 100mm, T = 45 °C), mobile phase of 5% ACN in H ₂ O (both with 0.05% TFA) was held for 1 min, then a gradient of 5-99% ACN over 6 min, then held at 99% ACN for 3 min, with a flow rate of 80 mL/min.

or

METHOD C. A Shimadzu LC-8A Series HPLC with an XBridge C18

OBD column (5 μιτι, 50 x 100mm), mobile phase of 5% ACN in H ₂ O (both with 0.05% TFA) was held for 1 min, then a gradient of 5-99% ACN over 14 min, then held at 99% ACN for 10 min, with a flow rate of 80 mL/min.

or

METHOD D. A Giison HPLC with an XBridge C18 column (δμηι, 100 x

50mm), mobile phase of 5-99% ACN in 20 mM NH ₄ QH over 10 min and then hold at 99 ACN for 2 min, at a flow rate of 80 mL/min.

Preparative supercritical fluid high performance liquid chromatography (SFC) was performed either on a Jasco preparative SFC system, an APS 1010 system from Berger instruments, or a SFC-PICLAB-PREP 200 (PIC SOLUTION, Avignon, France). The separations were conducted at 100-150 bar with a flow rate ranging from 40-60 mL/min. The column were heated to 35-40 °C. Mass spectra (MS) were obtained on an Agilent series 1 100 MSD using eiectrospray ionization (ESI) in positive mode unless otherwise indicated. Calculated (calcd.) mass corresponds to the exact mass.

Nuclear magnetic resonance (NMR) spectra were obtained on Bruker model DRX spectrometers. Definitions for multiplicity are as follows: s = singlet, d = doublet, t= triplet, q = quartet, m = multiplet, br = broad, !t will be understood that for compounds comprising an exchangeable proton, said proton may or may not be visible on an NMR spectrum depending on the choice of solvent used for running the NMR spectrum and the concentration of the compound in the solution.

Chemical names were generated using ChemDraw Ultra 12.0,

ChemDraw Ultra 14.0 (CambridgeSoft Corp., Cambridge, MA) or ACD/Name Version 10.01 (Advanced Chemistry).

Compounds designated as R ^* or S ^* are enantiopure compounds where the absolute configuration was not determined.

Intermediate 1 : 2-Bromo-1 -(3,3-difluoroazetidin-1 -vDethanone.

To a solution of 3,3-difiuoroazetidine hydrochloride (3 g, 23 mmol) and Et ₃ N (3.2 mL, 23 mmol) in ACN (29 mL) at -78 °C was added 2-bromoacetyi chloride (1 .9 mL, 23 mmol). The reaction mixture was allowed to slowly warm to room temperature. After 30 minutes, water was added and the aqueous phase was extracted with DCM (3x). The combined organic layers were dried (MgS0 ₄ ), filtered and evaporated to afford the title compound (3.45 g, 70 %). ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 4.66 (t, J = 12.5 Hz, 2H), 4.36 (t, J = 12.6 Hz, 2H), 4.26 (s, 2H).

Intermediate 2: 2-Bromo-1 -(3-fluoroazetidin-1 -vDethanone. The title compound was prepared in a manner analogous to Intermediate 1. This compound was isolated as a mixture of 2-bromo-1 ~(3-fluoroazetidin~1 - yl)ethanone and 2-chioro-1 -(3-fluoroazetidin-1 -yl)ethanone and was used in the next step without any further purification. ntermediate 3: (5-Fluoropyrimidin-2-yi)methyi methanesuifonate.

To a solution of (5-fluoropyrimidin-2-yl)methanol (100 mg, 0.78 mmol) in DCM (3 mL) was added Et ₃ N (0.16 mL, 1.2 mmol) followed by methanesuifonyl chloride (79 μί, 1 mmol) at 0 °C. After 30 minutes, wafer (10 mL) and a saturated aqueous solution of NaHCOs (10 mL) were added. The aqueous phase was extracted with DCM twice and the combined organics Iayers were dried ( gS0 ₄ ), filtered and evaporated to afford the title compound (160 mg, quantitative yield). The material was used in the next step without any further purification.

Intermediate 4: Pyrimidin-5-ylmethyi methanesuifonate.

To a solution of 5-pyrimidine methanol (1 10 mg, 0.999 mmol) in DCM (4 mL) was added Et ₃ N (0.21 mL, 1 .5 mmol) followed by methanesuifonyl chloride (0.10 mL, 1 .3 mmol) at 0 °C. After 30 minutes, water (10 mL) and a saturated aqueous solution of aHCOs (10 mL) were added. The aqueous phase was extracted with DCM twice and the combined organics Iayers were dried (MgS0 ₄ ), filtered and evaporated to afford the title compound (188 mg, quantitative yield). The material was used in the next step without any further purification. Intermediate 5: 6-Bromo-3-chloro-1 H-pyrroloi3,2-blpyridine.

To a solution of 6-bromo-1 H-pyrrolo[3,2-b]pyridine (3 g, 15 mmol) in D F (34 mL) cooled at 0 °C was slowly added NCS (2.4 g, 18 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. Water was then added and the mixture was stirred for 20 minutes. The title compound was collected via filtration and washed with water (2.6 g, 74%). ¹ H NMR (500 MHz, DMSO-cfe) δ 1 1 .74 (s, 1 H), 8.45 (d, J = 2.0 Hz, 1 H), 8.09 (d, J = 2.0 Hz, 1 H), 7.86 (d, J = 3.0 Hz, 1 H).

Intermediate 6: 6-Bromo-3-fiuoro-1 H-pyrrolof3,2-b]pyridine.

To a solution of 6-bromo~1 H~pyrrolo[3,2-b]pyridine (2 g, 10.2 mmol) and Seiectfluor ^® (4.3 g, 12.2 mmol) in ACN (20 mL) was added pyridine (6 mL). After 16 hours at room temperature, solvent was evaporated under reduced pressure. Purification (FCC, SiOa, 50-100% EtOAc in hexanes) gave the title compound (666 mg, 31 %). ¹ H NMR (500 MHz, DMSO-cf ₆ ) δ 1 1 .28 (s, 1 H), 8.41 (d, J = 2.0 Hz, 1 H), 8.04 (t, J = 2.2 Hz, 1 H), 7.71 (t, J = 2.6 Hz, 1 H). Intermediate 7: 6-Phenyl-1 H-pyrroloi3,2-blpyridine.

To a solution a 6-bromo-1 H-pyrrolo[3,2-b]pyridine (400 mg, 2.03 mmol) in dioxane (100 mL) was added phenylboronic acid (297 mg, 2.43 mmol), Pd(dppf)CI ₂ (149 mg, 0,203 mmol), Cs ₂ C0 ₃ (1 .9 g, 6,09 mmol) and water (10 mL). After 16 hours at 90 °C the reaction mixture cooled and was

concentrated under reduced pressure. Purification (FCC, SiOa, 0-100% EtOAc in hexanes) afforded the title compound (257 mg, 65%). !VIS (ESI): mass calcd. for Ci ₃ H ₁₀ N _2! 194.1 ; m/z found, 195.0 [M+H] ⁺ .

Intermediate 8: 3-Bromo-6-phenyl-1 H-pyrrolo[3,2-b]pyridine.

To a solution of 6-phenyl~1 H~pyrrolo[3,2-b]pyridine (Intermediate 7, 526 mg, 2.708 mmol) in DMF (6 mL) at 0 °C was added N-bromosuccinimide (NBS) (500 mg, 2.809 mmol) in small portions. The reaction mixture was stirred at 0 °C for 15 min. The reaction mixture was poured into water (25 mL). The precipitate was collected and washed with water (2 x 4 mL) and methanol (2 x 4 mL) to give the title compound (510 mg, 1 .867 mmol, 69%) as a light brown powder. MS (ESI): mass calcd. for C 3H ₉ Br ₂ , 272.0; m/z found, 273.0

[M+Hf. Ή NMR (300 MHz, DMSO-cfe) δ 1 1 .73 (s, 1 H), 8.71 (s, 1 H), 8.02 (s, 1 H), 7.88 (d, J = 2.9 Hz, 1 H), 7.74 (d, J = 7.6 Hz, 2H), 7.51 (t, J = 7.5 Hz, 2H), 7.40 (t, J = 7.3 Hz, 1 H).

Intermediate 9: 6-(3.5-Difluorophenyl)-1 H-pyrroloi3,2-b]pyridine.

The title compound was prepared in a manner analogous to Intermediate 7. MS (ESI): mass calcd. for C ₃ H ₈ F ₂ N ₂ , 230.07; m/z found, 231 = [M+H] ^{+ 1} H MR (400 MHz, DMSO- of ₆ ) δ 1 1.61 - 1 1 .38 (s, 1 H), 8.75 - 8.56 (d, J = 2.1 Hz, 1 H), 8.16 - 7.85 (m, 1 H), 7.77 - 7.65 (m, 1 H), 7.62 - 7.39 (m, 2H), 7.29 7.04 (tt, J = 9.4, 2,3 Hz, 1 H), 6,73 - 6.47 (d, J = 3.1 Hz, 1 H). Intermediate 10: 2-(6-Bromo-1 H-pyrrolo[3,2-b]pyridir¾-1 -yl)-1 -(pyrrolidin-1 -

To a solution of 6-bromo-1 H-pyrrolo[3,2-b]pyridine (1 g, 5.0 mmol) in D F (20 mL) at 0 °C was added NaH (284 mg, 7.1 mmol, 80% dispersion in oil). The reaction mixture was stirred for 30 minutes and 2-bromo-1 -(pyrrolidin-1 - yi)ethanone (1.02 g, 5.3 mmol) in DMF (5 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. Water (1 mL) was added and the reaction mixture was concentrated onto silica gel. Purification (FCC, S1O2, 0-20% MeOH in EtOAc) gave the title compound (quant, yield). ¹ H NMR (400 MHz, DMSO-cfe) δ 8.37 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.1 , 0.8 Hz, 1 H), 7.58 (d, J = 3.3 Hz, 1 H), 6.58 (dd, J = 3.3, 0.8 Hz, 1 H), 5.12 (s, 2H), 3.56 (t, J = 6.8 Hz, 2H), 3.37 - 3.25 (m, 2H), 2.01 - 1 .90 (m, 2H), 1 .86 - 175 (m, 2H).

!ntermediate 1 1 : 2-(6-Bromo-1 H-pyrrolo[3,2-blpyridin-1 -yl)-1 - morphoiinoethanone.

The title compound was prepared in a manner analogous to Intermediate 10, substituting 2-bromo-1 -morpholinoethanone for 2-bromo-1 -(pyrrolidin-1 - yi)ethanone. ¹ H NMR (500 MHz, DMSO-cfe) δ 8.37 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.58 (d, J = 3.3 Hz, 1 H), 6.59 (dd, J = 3.3, 0.9 Hz, 1 H), 5.24 (s, 2H), 3.69 (t, J = 4.8 Hz, 2H), 3.60 (t, J = 4.9 Hz, 2H), 3.54 (t, J = 4.8 Hz, 2H), 3.44 (t, J = 4.8 Hz, 2H).

The title compound was prepared ina manner analogous to Intermediate 10, substituting 2-bromo-1-(3,3-difluoroazetidin-1-yl)ethanone (Intermediate 1)for 2-bromo~1-(pyrroiidin~1~yl)ethanone. MS (ESI): mass calcd. for

Ο·! ₂ Η ₁₀ ΒΓΡ ₂ Ν ₃ Ο, 329,0; m/z found, 330,0 [M+H] ⁺ .

Intermediate 13: 2-(6-Bromo-1 H-pyrrolo[3,2-b]pyridin-1 -vh-1 -(3-fluoroazetidin- 1-yl)ethanone.

The title compound was prepared ina manner analogous to Intermediate 10, substituting 2-bromo-1-(3-fluoroazetidin-1-yl)ethanone (Intermediate 2) for 2- bromo-1-(pyrrolidin-1-yl)ethanone. MS (ESI): mass calcd. for Ci ₂ HnBrFIM ₃ 0, 311.0; m/z found, 312.0 [M+Hf.

The title compound was prepared in a manner analogous to Intermediate 10, using 1~(azetidin-1-yl)~2-bromoethanone and 6-bromo-1 H-pyrrolo[3,2~ bjpyridine. H NMR (500 MHz, DMSO-d ₆ ) δ 8,44 - 8,31 (d, J = 2.0 Hz, 1 H), 8.19 - 8.1 1 (m, 1 H), 7.66 - 7.43 (d, J = 3.3 Hz, 1 H), 6.64 - 6.50 (m, 1 H), 5.02 - 4.85 (s, 2H), 4.29 - 4.15 (m, 2H), 3.96 - 3.81 (m, 2H), 2,34 - 2,20 (m, 2H). Intermediate 15: 2-(6-bromo-3-fluoro-1 H-pyrrc>lo[3,2-blpyridin-1 -yl)-1 -(3,3- difluoroazetidin-1 -yl)ethanone.

The title compound was prepared ina manner analogous to Intermediate 10, substituting 2~bromo~N,N~dimethylacetamide for 2~bromo~1 -(pyrrolidin~1 - yl)ethanone and 6-bromo-3-fluoro-1 H-pyrroio[3,2-b]pyridine (Intermediate 6) for 6~bromo-1 H-pyrroio[3,2-b]pyridine. ¹ H NMR (500 MHz, DMSO-cfe) δ 8.42 (d, J = 1 .9 Hz, 1 H), 8.29 (t, J = 2.1 Hz, 1 H), 7.63 (d, J = 2.2 Hz, 1 H), 5.16 (s, 2H), 3.07 (s, 3H), 2.85 (s, 3H). Intermediate 16: 2-(6-Bromo-3-fluoro-1 H-pyrroloi3,2-b]pyridin-1 -νΠ-1 -(3,3- difluoroazetidin-1 -yl)ethanone.

The title compound was prepared ina manner analogous to Intermediate 10, using 2-bromo-1 -(3,3-difluoroazetidin-1 -yl)ethanone (Intermediate 1 ) and 6- bromo-3-fluoro-1 H-pyrroio[3,2-b]pyridine (Intermediate 6). ^! H NMR (500 MHz, DMSO- da) δ 8.52 - 8.39 (d, J = 1 .9 Hz, 1 H), 8.34 - 8.21 (m, 1 H), 7.73 - 7.53 (d, J = 2,2 Hz, 1 H), 5,07 - 4,89 (s, 2H), 4.83 - 4.56 (m, 2H), 4.46 - 4.25 (m, 2H).

The title compound was prepared ina manner analogous to Intermediate 10, using 2-bromo-1-(3-fluoroazetidin-1-yl)ethanone (Intermediate 2) and 6- bromo-3-fluoro-1H-pyrrolo[3,2-b]pyridine (Intermediate 6). ^! H NIV1R (500 MHz, DMSO- da) δ 8.51 -8.38 (d, J= 1.9 Hz, 1H), 8.36- 8.17 (t, J = 2.1 Hz, 1H), 7.70 - 7.63 (d, J = 2.2 Hz, 1 H), 5.60 - 5.48 (m, 0.5H), 5.48 - 5.31 (m, 0.5H), 5.07 - 4.79 (d, J = 2.2 Hz, 2H), 4,69 - 4.47 (m, 1 H), 4.40 - 4.17 (m, 2H), 4.14 -3.87 (m, 1H).

Intermediate 18: 2-(6-Bromo-3-fluoro-1 H-pyrroloi3.2-blpyridin-1 -yl)-1 - (pyrroiidin-1 -yPethanone.

The title compound was prepared in a manner analogous to Intermediate 6, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(pyrrolidin-1 -yi)ethanone (Intermediate 10). H HMR (500 MHz, DMSO- cfe) δ 8.50-8.36 (d, J= 1.9 Hz, 1H), 8.36-8.21 (t, J = 2.1 Hz, 1H), 7.76-7.57 (d, J = 2,2 Hz, 1H), 5.13- 4.86 (s, 2H), 3.62-3.47 (m, 2H), 3.41 -3.17 (s, 2H), 2.03-1.86 (m, 2H), 1.86-1.66 (m, 2H). Intermediate 19: 2-(6-Bromo-3-fluoro-1 H-pyrroloi3.2-b]pyridiri-1 -yl

The title compound was prepared in a manner analogous to Intermediate 6, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -y!)~1 -morpholinoethanone (Intermediate 1 1 ). MS (ESI): mass calcd. for C ₃ Hi ₃ BrFN ₃ G2, 341 .0; m/z found, 342.0 [M+H] ⁺ iiate 20: tert-Butyl 2-(6-(4-fluc

vDacetate.

Step A: 8-(4-Fluorophenyl)-1 H-pyrrolo[3.2-blpyridine. The title compound was prepared in a manner analogous to Intermediate 7. H NMR (400 MHz, DMSO-d ₆ ) 6 1 1 .39 (s, 1 H), 8.60 (d, J = 2.1 Hz, 1 H), 7.95 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.80 - 7.73 (m, 2H), 7.70 - 7.65 (m, 1 H), 7.36 - 7.28 (m, 2H), 6.60 - 6.56 (m, 1 H).

Step B: fert-Butyl 2-(6-(4-fluorophenyl)-1 H-pyrrolo[3,2-blpyridin-1 -vDacetate.

The title compound was prepared in a manner analogous to Intermediate 10. ^! H N MR (300 MHz, DMSO-d ₆ ) δ 8.65 (s, 1 H), 8.16 (s, 1 H), 7.79 (dd, J = 8.6, 5.5 Hz, 2H), 7.66 (d, J = 3.2 Hz, 1 H), 7.34 (t, J = 8.8 Hz, 2H), 6.61 (d, J = 3.0 Hz, 1 H), 5.13 (s, 2H), 1 .41 (s, 9H). Example 1 : 2-(3-Chloro-6-phenyl-pyrrolof3,2-blpyridin-1 -yl)-N-cvclopropy acetamide.

Step A: 8-Phenyl-1 H-pyrrolo[3,2-blpyridine. To a solution of 6-bromo-1 H- pyrrolo[3,2-b]pyridine (400 mg, 2.03 mmol) in dioxane (100 mL) was added phenylboronic acid (297 mg, 2.43 mmol), Pd(dppf)Cl2 (149 mg, 0.203 mmol), Cs ₂ C0 ₃ (1 .9 g, 6.09 mmol) and water (10 mL). After 16 h at 90 °C the reaction mixture cooled and was concentrated under reduced pressure. Purification (FCC, Si0 ₂ , 0-100% EtOAc in hexanes) afforded the title compound (257 mg, 65%). MS (ESI): mass caicd. for C13H10N2, 194.1 ; m/z found, 195.0 [M+H] ⁺ . Step B: 3-Chloro-8-phenyl-1 H-pyrrolo[3.2-b]pyridine. To a solution of 6- phenyl-1 H-pyrrolo[3,2-/)]pyridine (600 mg, 3.09 mmol) in N,N- dimethylformamide (6 mL) at 0 °C was added V-ch!orosuccinirnide (819 mg, 4.64 mmol) in several small portions. The reaction mixture was warmed to room temperature and the stirring was continued for 5 h. The mixture was poured into water (30 mL). The precipitate was collected and washed with warm methanol (5 mL) to afford the title compound (503 mg, 2.20 mmol, 71 %) as a pale brown powder. MS (ESI): mass calcd. For C13H3CIN2, 229.0; m/z found, 229 [M+Hf. H NMR (300 MHz, DMSO-d ₆ ) δ 1 1 .68 (s, 1 H), 8.71 (s, 1 H), 8.01 (s, 1 H), 7.86 (d, J = 2.9 Hz, 1 H), 7.74 (d, J = 7.5 Hz, 2H), 7.51 (t, J = 7.5 Hz, 2H), 7.40 (t, J = 7.3 Hz, 1 H).

Step C: 2-(3-Chloro-8-phenyl-pyrroloi3,2-b]pyridin-1 -yl)-N-cyclopropyl- acetamide. To a solution of 3~chloro~6-phenyl~1 H-pyrroio[3,2~d]pyridine (70 mg, 0.306 mmol) in anhydrous DMF (1 .4 mL) was added NaH (60%

dispersion, 18 mg, 0.46 mmol) at 0 °C in small portions under argon. The reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was cooled to 0 °C and to the mixture was added 2~bromo~ V- cyclopropylacetamide (81 mg, 0.46 mmol) in small portions. The reaction mixture was warmed to room temperature and the stirring was continued for 2 h. The reaction mixture was poured into ice water (10 ml_). The precipitate was collected and washed with water (2 x 3 mL). Purification (FCC, Si02, 100: 1 to 95:5 chloroform in MeOH). The product was triturated with warm ethanoi (1 mL) to give the title compound (30 mg, 0.09 mmol, 30%) as an off- white powder, MS (ESI): mass calcd. For Ci8H ₆ CiN ₃ 0, 325.1 ; m/z found, 328 [M+H] ^÷ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8.74 (s, 1 H), 8.34 (s, 1 H), 8.18 (s, 1 H), 7.83 (s, 1 H), 7.76 (d, J = 7.6 Hz, 2H), 7.52 (t, J = 7.5 Hz, 2H), 7.41 (t, J = 7.4 Hz, 1 H), 4.89 (s, 2H), 2.71 - 2.58 (m, 1 H), 0.68 - 0.57 (m, 2H), 0.51 - 0.33 (m, 2H).

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for Ci ₈ H ₁₅ CiFN ₃ 0, 343.1 ; m/z found, 344.0 [M+H] ⁺ . Ή NMR (300 MHz, DMSO-efe) δ 8.71 (s, 1 H), 8.31 (d, J = 4.2 Hz, 1 H), 8.17 (s, 1 H), 7.83 (s, 1 H), 7.79 (dd, J = 8.6, 5.3 Hz, 2H), 7.35 (t, J = 8.6 Hz, 2H), 4.88 (s, 2H), 2.71 - 2.60 (m, 1 H), 0.69 - 0.57 (m, 2H), 0.50 - 0.39 (m, 2H). Example 3: 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(4-fluorophenyl)pyrrolo[3,2- blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 1 . (ES!): mass calcd. for C18H15CIFN3O, 343.1 ; m/z found, 344.0 [M+H] ^÷ . ¹ H NMR (300 MHz, DMSO-tfe) δ 8.71 (s, 1 H), 8.20 (s, 1 H), 7.86 - 7.74 (m, 2h 7.79 (s, 1 H), 7.36 (t, J = 8.6 Hz, 2H), 5.01 (s, 2H), 4.24 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.8 Hz, 2H), 2.28 (quint, J = 7.8 Hz, 2H).

Example 4: 2-(3-Chloro-6-phenyl-pyrrolof3,2-blpyridin-1 -yl)-1 -pyrroiidin-1 -yl- ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ES!): mass calcd. for Ci9H ₁₈ C!N ₃ 0, 339.1 ; m/z found, 340.0 [M+H] ^{+ 1} H NMR (300 MHz, DMSO-de) δ 8.73 (s, 1 H), 8.24 (s, 1 H), 7.77 (s, 1 H), 7.77 (d, J = 7.8 Hz, 2H), 7.52 (t, J = 7.5 Hz, 2H), 7.41 (t, J = 7.3 Hz, 1 H), 5.19 (s, 2H), 3.58 (t, J = 6.8 Hz, 2H), 3.37 - 3.26 (m, 2H), 1.97 (quint, J = 6.7 Hz, 2H), 1 .81 (quint, J = 6.9 Hz, 2H).

Example 5: 2-(3-Chloro-6-phenyl-pyrroloi3,2-b]pyridin-1 -yl)-1 -morpholinO' ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for C19H18CIN3O2, 355.1 ; m/z found, 356.0 [M+H] ⁺ 'H NMR (300 MHz, DMSO-ds) δ 8.73 (s, 1 H), 8.22 (s, 1 H), 7.77 (s, 1 H), 7.76 (d, J = 7.0 Hz, 2H), 7.52 (t, J = 7.5 Hz, 2H), 7.41 (t, J = 7.3 Hz, 1 H), 5.31 (s, 2H), 3.90 - 3.37 (m, 8H). Example 6: 1 -(Azetidin-1 -yl)-2-(3-chloro-6-phenyl-pyrrolor3,2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd, for 0ι ₈ Ηί ₆ 0!Ν ₃ Ο, 325.1 ; m/z found, 326.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8.73 (s, 1 H), 8.21 (s, 1 H), 7.78 (s, 1 H), 7.77 (d, J = 7.2 Hz, 2H), 7.53 (t, J = 7.5 Hz, 2H), 7.41 (t, J = 7.3 Hz, 1 H), 5.02 (s, 2H), 4.25 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.28 (quint, J = 7.7 Hz, 2H). Example 7: 2-f3-Chloro-6-(4-fluorophenyl)pyrrolof3,2-blpyridin-1 -vH-1 - morphoiino-ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ES!): mass calcd. for C19H17CIFN3O2, 373.1 ; m/z found, 374.0 [M+H] ⁺ . H !MMR (300 MHz, DMSO-d ₆ ) δ 8.71 (s, 1 H), 8.21 (s, 1 H), 7.85 - 7.72 (m, 2H), 7.78 (s, 1 H), 7.36 (t, J = 8.7 Hz, 2H), 5.30 (s, 2H), 3.80 - 3.65 (m, 2H), 3.65 3.50 (m, 4H), 3.50 - 3.37 (m, 2H).

-(Azetidin-1 -yl)-2-f3-chloro-6-(m-tolvnpyrrolof3.2-blpyridin-1 ^■

The title compound was prepared in a manner analogous to Example 1 . MS (ES!): mass calcd. for Ci ₉ Hi ₈ ClN ₃ 0, 339.1 ; m/z found, 340.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ofe) δ 8.72 (s, 1 H), 8.19 (s, 1 H), 7.78 (s, 1 H), 7.58 (s, 1 H), 7.55 (d, J = 8.2 Hz, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.23 (d, J = 7.5 Hz, 1 H), 5.02 (s, 2H), 4.24 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.42 (s, 3H), 2.28 (quint, J = 7.8 Hz, 2H).

Example 9: 2-[3-Chloro-6-(4-fluorophenyl)pyrrolof3,2-blpyridin-1 -yll-1 -

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for C ₉ Hi7CiFN ₃ 0, 357.1 ; m/z found, 358.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 8.71 (s, 1 H), 8.22 (s, 1 H), 7.80 (dd, J = 8.4, 6.1 Hz, 2H), 7.77 (s, 1 H), 7.35 (t, J = 8.6 Hz, 2H), 5.18 (s, 2H), 3.58 (t, J = 6.8 Hz, 2H), 3.36 - 3.20 (m, 2H), 1 .97 (quint, J = 6.8 Hz, 2H), 1 .81 (quint, J = 6.8 Hz, 2H). Example 10: 2-f3-Chloro-6-f m-toly0pyrrolQi3,2-b]pyridin-1 -yll-N-cvclopropyl- acetamide.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd, for 0ι ₉ Ηί ₈ 0!Ν ₃ Ο, 339.1 ; m/z found, 340.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8.72 (s, 1 H), 8.33 (d, J = 4.2 Hz, 1 H), 8.15 (s, 1 H), 7.82 (s, 1 H), 7.57 (s, 1 H), 7.53 (d, J = 7.6 Hz, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 H), 4.89 (s, 2H), 2.70 - 2.58 (m, 1 H), 2.41 (s, 3H), 0.70 - 0.53 (m, 2H), 0.50-0.29 (m, 2H).

Example 1 1 : 1 -(Azetidin-1 -yl)-2-(3-bromo-6-phenyl-pyrrolof3.2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 14.

(ESI): mass calcd. for CieHieBrN ₃ 0, 369.0; m/z found, 370.0 [M+H] ⁺ . ¹ H NMR

(300 MHz, DMSO-d ₆ ) δ 8.74 (s, 1 H), 8.21 (s, 1 H), 7.81 (s, 1 H), 7.77 (d, J = 7.7 Hz, 2H), 7.53 (t, J = 7.5 Hz, 2H), 7.41 (t, J = 7.3 Hz, 1 H), 5.03 (s, 2H), 4.25 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.8 Hz, 2H), 2.30 (quint, J = 7.5 Hz, 2H).

Example 12: 2-f3-Chloro-6-f m-toly0pyrrQlQf3,2-b]pyridin-1 -yll-1 -pyrrolidin-1 -vi- ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for C ₂ oH ₂ oCIN ₃ 0, 353.1 ; m/z found, 354.0 [M+H] ^{+ 1} H HMR (300 MHz, DMSO-cfe) δ 8,71 (s, 1 H), 8.21 (s, 1 H), 7.76 (s, 1 H), 7.57 (s, 1 H), 7.54 (d, J = 7.8 Hz, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 H), 5.19 (s, 2H), 3.59 (t, J = 6.8 Hz, 2H), 3.39 - 3.24 (m, 2H), 2.41 (s, 3H), 1 .97 (quint, J = 6.8 Hz, 2H), 1 .81 (quint, J = 6.8 Hz, 2H).

The title compound was prepared in a manner analogous to Example 1 . MS (ES!): mass calcd. for C2OH2QC!N ₃ 0 ₂ , 369.1 ; m/z found, 370.0 [M+H] ⁺ . Ή NMR (300 MHz, DMSO-cfe) δ 8.70 (s, 1 Η), 8.19 (s, 1 Η), 7.77 (s, 1 H), 7.56 (s, 1 Η), 7.53 (d, J = 7.6 Hz, 1 Η), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 Η), 5.31 (s, 2H), 3.85 - 3.65 (m, 2H), 3.65 - 3.50 (m, 4H), 3.50 - 3.37 (m, 2H), 2.41 (s, 3H). Example 14: 2-(3-Bromo-6-phenyl-pyrrolor3.2-blpyridin-1 -vD-N-cvclopropyl- acetamide.

Step A: 3-Bromo-6-phenyl-1 H-pyrrolo[3,2-b]pyridine. To a solution of 6- phenyi-1 H-pyrrolo[3,2-b]pyridine (Intermediate 7, 526 mg, 2.708 mmol) in DMF (6 mL) at 0 °C was added N-bromosuccinimide (NBS) (500 mg, 2.809 mmol) in small portions. The reaction mixture was stirred at 0 °C for 15 min. The reaction mixture was poured into water (25 mL). The precipitate was collected and washed with water (2 x 4 mL) and methanol (2 x 4 mL) to give the title compound (510 mg, 1 .867 mmol, 69%) as a light brown powder. MS (ESI): mass calcd. for Ci ₃ H ₉ BrN _2! 272.0; m/z found, 273,0 [M+Hf. H NMR (300 MHz, DMSO-cfe) δ 1 1.78 (s, 1 H), 8.71 (s, 1 H), 8.02 (s, 1 H), 7.88 (d, J = 2.9 Hz, 1 H), 7.74 (d, J = 7.6 Hz, 2H), 7.51 (t, J = 7.5 Hz, 2H), 7.40 (t, J = 7.3 Hz, 1 H).

Step B: 2-(3-Bromo-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yp-N-cyclopropyi- acetamide. To a solution of 3-bromo-6-phenyl-1 H-pyrrolo[3,2-b]pyridine (60 mg, 0.22 mmol) in anhydrous DMF (1 .5 mL) was added NaH (60%

dispersion, 13 mg, 0.33 mmol) in small portions at 0 °C under argon. The reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was cooled to 0 °C and to the mixture was added 2-bromo- V~ cyclopropylacetamide (43 mg, 0.24 mmol) in small portions. The reaction mixture was warmed to room temperature and the stirring was continued for 1 h. The reaction mixture was poured into ice water (6 mL) and the precipitate was collected and washed with water (2 x 0.5 mL). The crude product was recrystallized from ethanol (1 .7 mL) to afford the title compound (49 mg, 0.13 mmol, 60%) as a white powder. MS (ES!): mass calcd. for Ci ₈ Hi ₆ BrlM ₃ 0, 369.0; m/z found, 370 [M+Hj ⁺ , H NMR (300 MHz, DMSO-d ₆ ) δ 8.74 (s, 1 H), 8.35 (d, J = 4.1 Hz, 1 H), 8.17 (s, 1 H), 7.85 (s, 1 H), 7.76 (d, J = 7.5 Hz, 2H), 7.52 (t, J = 7.5 Hz, 2H), 7.41 (t, J = 7.3 Hz, 1 H), 4.91 (s, 2H), 2.71 - 2.59 (m, 1 H), 0.68 - 0.55 (m, 2H), 0.49 - 0.36 (m, 2H).

Example 15: 2~(3-BromQ~6-phenyl~pyrroloi3,2-b]pyridin-1 -yl)-1 -pyrrolidin-1 -yl ethanone.

The title compound was prepared in a manner analogous to Example 14. MS (ES!): mass calcd. for Ci ₉ H ₁₈ BrN ₃ 0, 383.1 ; m/z found, 384.0 +Hf. Ή NMR (300 MHz, DMSO-C ) δ 8.73 (s, 1 H), 8.23 (s, 1 H), 7.79 (s, 1 H), 7.76 (d, J = 7.8 Hz, 2H), 7.52 (t, J = 7.5 Hz, 2H), 7.40 (t, J = 7.3 Hz, 1 H), 5.20 (s, 2H), 3.59 (t, J = 6.8 Hz, 2H), 3.34 - 3.23 (m, 2H), 1.97 (quint, J = 6.8 Hz, 2H), 1 .82 (quint, J = 6.8 Hz, 2H).

Example 16: 2-(3-Bromo-6-phenyl-pyrrolo[3,2-blpyridin-1 -yl)-1 -morpholino- ethanone.

The title compound was prepared in a manner analogous to Example 14. MS (ESI): mass calcd. for Ci ₉ H ₁₈ BrN ₃ G2, 399.1 ; m/z found, 400.0 [M+H] ⁺ H NMR (300 MHz, DMSO-d ₆ ) δ 8.73 (s, 1 H), 8.22 (s, 1 H), 7.80 (s, 1 H), 7.75 (d, J = 7.7 Hz, 2H), 7.52 (t, J = 7.5 Hz, 2H), 7.41 (t, J = 7.3 Hz, 1 H), 5.32 (s, 2H), 3.80 - 3.65 (m, 2H), 3.65 - 3.50 (m, 4H), 3.51 - 3.37 (m, 2H). -r3-Bromo-6-(4-fluorophenyl)pyrrolor3.2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 14. MS (ESI): mass calcd. for Ci ₈ Hi ₅ BrFN ₃ 0, 387.0; m/z found, 388.0 [M+H] ⁺ . H N MR (300 MHz, DMSO-cfe) δ 8.72 (s, 1 H), 8.34 (d, J = 4.1 Hz, 1 H), 8.17 (s, 1 H), 7.85 (s, 1 H), 7.80 (dd, J = 8.5, 5.5 Hz, 2H), 7.38 (t, J = 8.7 Hz, 2H), 4.90 (s, 2H), 2.70 - 2.58 (m, 1 H), 0.68 - 0.57 (m, 2H), 0.50 - 0.38 (m, 2H).

The title compound was prepared in a manner analogous to Example 14. MS (ES!): mass calcd. for C ₈ H _{l 5} BrFN ₃ 0, 387.0; m/z found, 388.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 8.71 (s, 1 H), 8.20 (s, 1 H), 7.87 - 7.74 (m, 2H), 7.81 (s, 1 H), 7.36 (t, J = 8.7 Hz, 2H), 5.02 (s, 2H), 4.25 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.28 (quint, J = 7.7 Hz, 2H).

Example 19: 2-r3-Bromo-6-(4-fluorophenyl)pyrrolor3,2-blpyridin-1 -yll-1 ^■

The title compound was prepared in a manner analogous to Example 14. MS (ES!): mass calcd. for Ci ₉ Hi ₇ BrFN ₃ 0, 401 .1 ; m/z found, 402.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8.71 (s, 1 H), 8.22 (s, 1 H), 7.88 - 7.70 (m, 2H), 7.79 (s, 1 H), 7.35 (t, J = 8.7 Hz, 2H), 5.19 (s, 2H), 3.58 (t, J = 6.8 Hz, 2H), 3.38 - 3.25 (m, 2H), 1 .97 (quint, J = 6.7 Hz, 2H), 1 .81 (quint J = 6.8 Hz, 2H).

Example 20: 2-f3-Bromo-6-(4-fluorophenyl)pyrrolof3,2-blpyridin-1 -νΠ-1 -

The title compound was prepared in a manner analogous to Example 14. MS (ESI): mass calcd. for C^H^BrFNsOs, 417.0; m/z found, 418.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 8.71 (s, 1 H), 8,20 (s, 1 H), 7.86 - 7.74 (m, 2H), 7.80 (s, 1 H), 7.36 (t, J = 8.6 Hz, 2H), 5.31 (s, 2H), 3.76 - 3.65 (m, 2H), 3.64 - 3.51 (m, 4H), 3.51 - 3.38 (m, 2H).

Example 21 : 2-f3-Bromo-6-(m olyl)pyrroloi3,2-b]pyridin-1 -yll-N-cyclopropyl- acetamide.

The title compound was prepared in a manner analogous to Example 14. MS (ESI): mass calcd. for C ₉ Hi ₈ BrN ₃ 0, 383.1 ; m/z found, 384.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8,72 (s, 1 H), 8.35 (d, J = 4.1 Hz, 1 H), 8.14 (s, 1 H), 7.84 (s, 1 H), 7.57 (s, 1 H), 7.54 (d, J = 7.7 Hz, 1 H), 7.40 (t, J = 7,6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 H), 4.90 (s, 2H), 2.71 - 2.59 (m, 1 H), 2.41 (s, 3H), 0.70 - 0.57 (m, 2H), 0.50 - 0.37 (m, 2H).

The title compound was prepared in a manner analogous to Example 14. MS (ESI): mass calcd. for C ₉ Hi8BrN ₃ G, 383.1 ; m/z found, 384.0 [M+Hf. Ή NMR (300 MHz, DMSO-de) δ 8.72 (s, 1 H), 8.19 (s, 1 H), 7.80 (s, 1 H), 7.58 (s, 1 H), 7.53 (d, J = 7.7 Hz, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 H), 5.03 (s, 2H), 4.25 (t, J = 7.8 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.41 (s, 3H), 2.28 (quint, J = 7.8 Hz, 2H).

Example 23: 2-i3-Bromo-6-(m-tolyl)pyrrolo[3,2-b1pyridin-1 -yl]-1 -pyrrolidin-1 -yl- ethanone.

The title compound was prepared in a manner analogous to Example 14. MS (ESI): mass calcd. for C2oH ₂ oBnM ₃ 0, 397.1 ; m/z found, 398.0 [!V H-H] ^{÷ 1} H NMR (300 MHz, DMSO-de) δ 8.71 (s, 1 Η), 8.20 (s, 1 Η), 7.78 (s, 1 Η), 7.57 (s, 1 Η), 7.54 (d, J = 7.5 Hz, 1 Η), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 Η), 5.20 (s, 2H), 3.59 (t, J = 6.8 Hz, 2H), 3.33 - 3.24 (m, 2H), 2.41 (s, 3H), 1 .96 (quint, J = 6.7 Hz, 2H), 1 ,82 (quint, J = 6.8 Hz, 2H). Example 24: 2-i3-Bromo-6-(ni-tolvnpyrroloi3,2-b]pyridir¾-1 -yl]-1 -morpholino- ethanone.

The title compound was prepared in a manner analogous to Example 14. S (ESI): mass calcd. for C ₂ oH2oBrN ₃ 02, 413.1 ; m/z found, 414.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-d ₆ ) δ 8.71 (s, 1 H), 8.19 (s, 1 H), 7.79 (s, 1 H), 7.56 (s, 1 H), 7.54 (d, J = 7.6 Hz, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 H), 5.32 (s, 2H), 3.93-3.66 (m, 2H), 3.66-3.50 (m, 4H), 3.50-3.37 (m, 2H), 2.41 (s, 3H).

Example 25: 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo 3,2-b]pyridin-1 - yi]-1 -(3,3-difluoroazetidin-1 -vQethanone.

The title compound was prepared in a manner analogous to Example 1 . MS

(ESI): mass calcd. for C19H ₁ 5CIF3N3O, 393.1 ; m/z found, 394.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-cfe) δ 8.71 (s, 1 H), 8.20 (s, 1 H), 7.78 (s, 1 H), 7.68 (d, J = 6.8 Hz, 1 H), 7.63 - 7.52 (m, 1 H), 7.29 (t, J = 9.1 Hz, 1 H), 5.14 (s, 2H), 4.76 (t, J = 12.5 Hz, 2H), 4.38 (t, J = 12.6 Hz, 2H), 2.34 (s, 3H). Example 26: 2-i3-Chloro-6-(4-fluoro-3-methyl-phenvnpyrrolo[3.2-b]pyridir i-1 ^■

The title compound was prepared in a manner analogous to Example 1. MS (ESI): mass calcd. for C19H16CIF2N3O, 375,1; m/z found, 376,0 [M+Hf. H NMR (300 MHz, DMSO-cfe) δ 8.70 (s, 1H), 8.19 (s, 1H), 7.78 (s, 1H), 7.68 (d, J = 7.5 Hz, 1 H), 7.64 - 7.54 (m, 1 H), 7.28 (t, J = 9.1 Hz, 1 H), 5.62 - 5.32 (m, 1H), 5.07 (s, 2H), 4.67-4,49 (m, 1H), 4,45-4.13 (m, 2H), 4.08-3.86 (m, 1H), 2.34 (s, 3H).

Example 27: 2-[6-(4-Fluorophenyl)-3-methyl-pyrrolor3,2-blpyridin-1 -vil- -

Step A: 6-(4-Fiuorophenyl)-1 H-pyrroloi3.2-blpyridine. The title compound was prepared in a manner analogous to Example 1 , Step A. H NMR (400 MHz, DMSO-cfe) δ 11.39 (s, 1H), 8.60 (d, J = 2.1 Hz, 1H), 7.95 (dd, J = 2.1, 0.9 Hz, 1 H), 7.80 - 7.73 (m, 2H), 7.70 - 7.65 (m, 1 H), 7.36 - 7.28 (m, 2H), 6,60 - 6.56 (m, 1H).

Step B: fert-Butyl 2-(6-(4-fluorophenyl)-1 H-pyrrolo[3,2-blpyridin-1-yl)acetate. The title compound was prepared in a manner analogous to Example 1 , Step C, using tert-butyl 2-bromoacetate and 6-(4-fiuorophenyi)-1H-pyrrolo[3,2- bjpyridine . ¹ H NMR (300 MHz, DMSG-d ₆ ) δ 8.65 (s, 1H), 8.16 (s, 1H), 7.79 (dd, J = 8.6, 5.5 Hz, 2H), 7.66 (d, J = 3.2 Hz, 1 H), 7.34 (t, J = 8.8 Hz, 2H), 6.61 (d, 3.0 Hz, 1 H), 5.13 (s, 2H), 1 .41 (s, 9H).

Step C: fe/f-Butyl 2-(3-bromo-6-(4-fluorophenyl)-1 H-pyrrolo[3,2-blpyridin-1 - yQacetate. To a solution of ferf-butyl 2~(6-(4~fluorophenyl)-1 H-pyrrolo[3,2~ b]pyridin-1 -yl)acetate (516 mg, 1 ,58 mmol) in DMF (10 mL) was added N- bromosuccinimide (NBS) (281 mg, 1 .58 mmol) in small portions. The reaction mixture was stirred at 50 °C for 2 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organics were dried (MgS0 ₄ ), filtered, and concentrated. Purification (FCC, S1O2, 0-100%EtOAc/hexanes) afforded the title compound (640 mg, 37%). vDacetate. Pd(PPh ₃ ) ₂ Cl2 (272 mg, 0.39 mmol) was added to a solution of tert- butyi 2~(3-bromo~6~(4-fiuorophenyi)-1 H-pyrrolo[3,2-b]pyridin~1 -yi)acetate (1 .6 g, 3.9 mmol), tetramethylstannane (2.1 mL, 15 mmol) and LiCI (656 mg, 15 mmol) in DMF (5 mL) in a sealed tube. The reaction mixture was heated to 1 10 °C for 12 hours and water followed by EtOAc was added. The organic layer was separated, dried over MgS0 ₄ , filtered and evaporated. Purification (FCC, SiC ^» 2,0-50% EtOAc in heptane) gave the title compound (1 .3 g, 22%). MS (ESI): mass calcd. for C2oH2 FN ₂ 0 _2i 340.2; m/z found, 341 .0 [M+H] ⁺ . Step E: 2-(6-(4-Fluorophenyl)-3-methyl-1 H-pyrroloi3,2-b1pyridin-1 -yl)acetic acid. To a solution fe f-butyl 2-(6-(4-fluorophenyl)-3-methyl-1 H-pyrroio[3,2- b]pyridin-1 -yl)acetate (290 mg, 0.85 mmoi) in DCM (6 mL) cooled at 0 °C was added TFA (6 mL, 78 mmoi) dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. The volatiles were evaporated and the crude was used directly in the next step without any further purification.

Step F: 2-f6-(4-Fluorophenyl)-3-methyl-pyrrolo[3,2-blpyridin-1 -yll-1 -pyrrolidin- 1 -yi-ethanone. To a solution of 2-(6~(4~fiuorophenyl)~3-methyi~1 H~pyrrolo[3,2- b]pyridin-1 -yi)acetic acid (80 mg, 0.28 mmoi) in DMF (5 mL) was added DIPEA (151 μί, 1 .1 mmol) and HBTU (160 mg, 0.42 mmoi). After 30 minutes, pyrrolidine (35 μί, 0.42 mmol) in D!VIF (0.2 mL) was added and the reaction mixture was stirred for another 30 minutes. A saturated aqueous solution of NaHCO ₃ was added followed by EtOAc. The organic phase was separated, dried over MgS0 _4l filtered and evaporated. Purification (FCC , S 1O2, 0-100% EtOAc in heptane) gave the title compound (31 mg, 32%). MS (ESI): mass caicd. for C ₂ QH ₂ OFN ₃ 0, 337.2; m/z found, 338.0 [M+H] ⁺ . H NMR (300 MHz, DMSO) δ 8.60 (d, J = 1 .6 Hz, 1 H), 8.05 (d, J = 1 .4 Hz, 1 H), 7.82 - 7.69 (m, 2H), 7.42 - 7.25 (m, 3H), 5.09 (s, 2H), 3.57 (t, J = 6.7 Hz, 2H), 3.33 - 3.24 (m, 2H), 2.30 (s, 3H), 2.02 - 1 ,88 (m, 2H), 1 ,87 - 1 .72 (m, 2H).

Example 28: 2-[6-(4-Fluorophenyl)-3-methyl-pyrrolo[3,2-blpyridin-1 -yll-1 - morpholino-ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C20H20FN3O2, 353.2; m/z found, 354.0 [M+H] ⁺ . ^! H NMR (300 MHz, DMSO) δ 8.59 (d, J = 1 .6 Hz, 1 H), 8.02 (d, J = 1 .7 Hz, 1 H), 7.75 (dd, J = 8.5, 5.6 Hz, 2H), 7.39 - 7.25 (m, 3H), 5.21 (s, 2H), 3.75 - 3.64 (m, 2H), 3.64 - 3.51 (m, 4H), 3.49 - 3.39 (m, 2H), 2.30 (s, 3H).

Step A: 1 -(Azetidin-1 -yl)-2-(6-brQmo-3-chloro-1 H-pyrroio[3,2-b]pyridin-1 - yPethanone. To a solution of 6-bromo-3-chloro-1 H-pyrrolo[3,2-b]pyridine (Intermediate 5, 250 mg, 1 .08 mmol) in DMF (60 mL) at 0 °C was added IMaH (60 mg, 1 ,51 mmol, 60% dispersion in oil). The reaction mixture was warmed to room temperature and stirred for 30 minutes and then cooled to 0 °C followed by the addition of a solution of 1 -(azetidin-1 -yl)-2-bromoethanone (1 .29 mmol) in DMF. The reaction mixture was warmed to room temperature and stirred for 12 hours. Water was added and the mixture was extracted with EtOAc. The combined organic layers were dried (MgSO^), filtered and evaporated. Purification (FCC, SiOa, 0-100% EtOAc in hexanes) afforded the title compound (247 mg, 70%).

MS (ESI): mass calcd. for C^HnBrCINsO, 327.0; m/z found, 328.0 [M+H] ⁺ . Step B: 1 -(Azetidin-1 -yl)-2-r3-chloro-6-(3,4-difluorophenyl)pyrrolor3,2- b]pyridin-1 -yllethanone. The title compound was prepared in a manner analogous to Example 1 , Step A. MS (ES!): mass calcd. for C18H14CIF2N3O, 361 .1 ; m/z found, 361 .9 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.76 (d, J = 1 .9 Hz, 1 H), 8.27 (d, J = 1 .9 Hz, 1 H), 7.90 (ddd, J = 12.3, 7.8, 2.2 Hz, 1 H), 7.81 (s, 1 H), 7.69 - 7.52 (m, 2H), 5.01 (s, 2H), 4.25 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.36 - 2.22 (m, 2H). Example 30: 2-r3-Chloro-6-f3.4-difluorophenyl)pyrTolof3.2-blpyridin-1 -νΠ-1 -(3- fluoroazetidin-1 -ypethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for Ci ₈ H ₁₃ ClF3N ₃ 0, 379.1 ; m/z found, 380.0 [M+Hf. H NMR (300 MHz, DMSO-d ₆ ) δ 8.76 (s, 1 H), 8.28 (s, 1 H), 8.89 (ddd, J = 10.4, 7.3, 1 .8 Hz, 1 H), 7.82 (s, 1 H), 7.72 - 7.49 (m, 2H), 5.48 (d, J = 57.3 Hz, 1 H), 5.07 (s, 2H), 4.70 - 4.46 (m, 1 H), 4.37 (dd, J = 26.4, 15.7 Hz, 1 H), 4.29 - 4.1 1 (m, 1 H), 3.98 (dd, J = 25.0, 1 1.6 Hz, 1 H). -r6-(4-Fluorophenyl)-2-methyl-pyrrolo[3,2-blpyridin-1 -yll-1 -

Step A: 2-Chloro-5-(4-fluorophenyl)pyridin-3-amine. To a solution of 5-bromo- 2-chloropyridin-3-amine (5 g, 24 mmol) and (4-fluorophenyl)boronic acid (4 g, 29 mmo!) in dioxane (100 mL) and water (25 mL) was added K ₃ P0 ₄ ( 5 g, 72 mmol) followed by PdCi ₂ (dtbpf) (393 mg, 0.60 mmol). The reaction mixture was degassed and then heated to 80 °C for 2 hours. Once cooled to room temperature water and EtOAc were added to the reaction mixture. The aqueous phase was extracted with EtOAc (3x). The combined organic layers were washed with water dried (Na ₂ SO ₄ ), filtered and evaporated to give the title compound (6 g, 76%). The crude was used in the next step without any further purification.

Step B: 5-(4-Fluorophenyl)-2-(prop-1 -vn-1 -yl)pyridin-3-amine. To a solution of 2-chloro-5-(4-fluorophenyl)pyridin-3-amine (2 g, 6.7 mmol) and trimethy!(prop- 1 -yn-1 -yl)silane (12 mL, 82 mmol) in DMF (100 mL) was added Pd(PPh ₃ ) ₂ CI ₂ (600 mg, 0.86 mmol), copper(l) iodide (100 mg, 0.53 mmol), CsF (13 g, 86 mmol) and Et ₃ N (22 mL, 158 mmol). The reaction mixture was stirred at 90 °C for 5 hours. The volatiles were evaporated and water was added to the residue and extracted 3 times with EtOAc. The combined organic layers were dried (Na ₂ SO ₄ ), filtered and evaporated. Purification (FCC, SiO ₂ , 0-80% EtOAc in petroleum ether) gave the title compound (250 mg, 14%). MS (ESI): mass caicd. for Ci ₄ Hn FN ₂ , 226.1 ; m/z found, 227.0 [M+H] ^T

Step C: 2-(6-(4-Fluorophenyl)-2-methyl-1 H-pyrrolo[3,2-blpyridin-1 -yl)acetic acid. To a solution of 5-(4-fluorophenyl)-2-(prop-1 -yn-1 -yl)pyridin-3-amine (100 mg, 0.44 mmol) in DMF (10 mL), cooled at 0 °C, was added NaH (35 mg, 0.88 mmol, 60% dispersion in oil). The reaction mixture was then allowed to warm to room temperature. After 12 hours, the reaction was cooled to 0 °C and NaH (25 mg, 0.63 mmol, 60% dispersion in oil) was added and stirred at this temperature for 30 minutes. Ethyl 2-bromoacetate (60 μΙ_, 0,54 mmol) was added dropwise and the mixture was stirred at room temperature for 5 hours. At 0 °C was added water and the aqueous phase was extracted with MTBE. The aqueous layer was acidified with 1 M HCI and the volatiles were evaporated to afford the title compound (100 mg, 55%). The crude was used in the next step without any further purification. MS (ES!): mass calcd. for C16H13F 2O2, 284.1 ; m/z found, 285.0 [M+H] ⁺

Step D: 2-f6-(4-Fluorophenyl)-2-methyl-pyrrolo[3,2-blpyridin-1 -yll-1 - mixture of intermediate of 2-(6-(4-fiuorophenyl)-2- methyl- H-pyrrolo[3,2-b]pyridin-1 -yl)acetic acid (100 mg, 0.24 mmol), morphoiine (37 mg, 0.43 mmol), HATU (170 mg, 0.45 mmol) and Et ₃ N (63 μΙ_, 0.45 mmol) in DMF (5 mL) was stirred at room temperature for 1 hour. Water was added and the aqueous phase was extracted 3 times with EtOAc. The combined organic layers were dried (Na ₂ S0 ), filtered and evaporated.

Purification by via HPLC Method A gave the title compound (30 mg, 33%). MS (ESI): mass calcd. for C20H2QFN3O2, 353.2; m/z found, 354.1 [M+H] ⁺ . H NMR (400 MHz, DMSO- fe) δ 8.53 (d, J = 1 .5 Hz, 1 H), 8.02 (s, 1 H), 7.76 (dd, J = 5.5, 8.5 Hz, 2H), 7.32 (t, J = 8.9 Hz, 2H), 6.38 (s, 1 H), 5.25 (s, 2H), 3.72 (br. s., 2H), 3,61 (d, J = 14.6 Hz, 4H), 3.44 (br. s., 2H), 2.34 (s, 3H).

Example 32: N-Cyclopropyl-2-[6-(4-fiuorophenyi ^' )-3-methyi-pyrroloi3,2-

The title compound was prepared in a manner analogous to Example 27. MS

(ESI): mass calcd. for Ci ₉ Hi ₈ FN ₃ 0, 323.1 ; m/z found, 324.0 [M+H] ⁺ . Ή NMR (300 MHz, CDC ) δ 8.72 (s, 1 H), 7.75 - 7.48 (m, 3H), 7.36 - 7.03 (m, 3H), 5.47 (br s, 1 H), 4.75 (s, 2H), 2.72 - 2.60 (m, 1 H), 2.45 (s, 3H), 0.91 - 0.63 (m, 2H), 0.48 - 0.15 (m, 2H). -(Azetidin-1 -yl)-2-r6-(4-fluorophenyl)-3-methyl-pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 27. S (ESI): mass calcd. for Ci ₉ H ₁₈ FN ₃ G, 323.1 ; m/z found, 324.0 [M+H] ⁺ . Ή NMR (300 MHz, DMSO-d ₆ ) δ 8.61 (s, 1 H), 8.04 (s, 1 H), 7.82 - 7.70 (m, 2H), 7.43 - 7.25 (m, 3H), 4.93 (s, 2H), 4.19 (t, J = 7.4 Hz, 2H), 3.89 (t, J = 7.4 Hz, 2H), 2.37 - 2.15 (m, 5H). Example 34: 2-i3-Chloro-6-(3.4-difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - (3,3-difluoroazetidin-1 -yl)ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for Ci ₈ H ₁₂ CiF N ₃ 0, 397.1 ; m/z found, 398.0 [M+Hf. H NMR (300 MHz, DMSO-d ₆ ) δ 8.77 (s, 1 H), 8.28 (s, 1 H), 7.88 (dd, J = 12.0, 8.2 Hz, 1 H), 7.81 (s, 1 H), 7.72 - 7.52 (m, 2H), 5.14 (s, 2H), 4.76 (t, J = 12.4 Hz, 2H), 4.38 (t, J = 12.6 Hz, 2H).

-r3-Chloro-6-f4-fluoro-3-(trifluoromethyl)phenyllpyrrolo[ 3,2-

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass ca!cd. for CigHisCiFsNsO, 429,1 ; m/z found, 430,0 [M+H] ⁺ . H NMR (300 MHz, DMSO-cfe) δ 8.78 (d, J = 1 .9 Hz, 1 H), 8.32 (d, J = 2.0 Hz, 1 H), 8.18 - 8.06 (m, 2H), 7.84 (s, 1 H), 7.69 (t, J = 9.6 Hz, 1 H), 5.62 - 5.32 (m, 1 H), 5.09 (s, 2H), 4.68 - 4,48 (m, 1 H), 4,45 - 4.15 (m, 2H), 4.07 - 3.86 (m, 1 H).

Example 36: 2-r3-Chloro-6-r3-(trifluoromethyl)phenyllpyrrolof3,2-blpyrid in-1 - vH-1 -(3,3-difiuoroazetidin-1 -yQethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for dgHisCIFsNsO, 429.1 ; m/z found, 430.0 [M+H] ⁺ H NMR (300 MHz, DMSO-d ₆ ) δ 8.81 (s, 1 H), 8.34 (s, 1 H), 8.15 - 7.98 (m, 2H), 7.84 (s, 1 H), 7.81 - 7.70 (m, 2H), 5.17 (s, 2H), 4.76 (t, J = 12.5 Hz, 2H), 4.38 (t, J = 12,5 Hz, 2H). -r6-(4-Fluorophenyl)-2-methyl-pyrrolo[3,2-blpyridin-1 -yll-1 ^■

The title compound was prepared in a manner analogous to Example 31 . MS (ES!): mass calcd. for C20H2QFN3O, 337.2; m/z found, 338.1 [M+H] ^{+ 1} H NMR (400 MHz, CDCI ₃ ) δ 8.58 (br. s., 1 H), 7.48 - 7.62 (m, 3H), 7.15 (t, J = 8.7 Hz, 2H), 6.55 (s, 1 H), 4.82 (s, 2H), 3.54 (t, J = 7.0 Hz, 2H), 3.48 (t, J = 6.9 Hz, 2H), 2.47 (s, 3H), 2.06 (quin, J = 6.8 Hz, 2H), 1 .84 - 1 .98 (m, 2H).

The title compound was prepared in a manner analogous to Example 31 . MS (ES!): mass calcd. for Ci ₉ Hi ₈ FN ₃ 0, 323.1 ; m/z found, 324.2 [M+H] ⁺ . ¹ H NMR (400 MHz, CDCI3) δ 8,66 (br. s., 1 H), 7.50 - 7.63 (m, 3H), 7.12 - 7.23 (m, 2H), 6.57 (s, 1 H), 5.39 (br. s., 1 H), 4.75 (s, 2H), 2.67 (qt, J = 3.6, 7.1 Hz, 1 H), 2.45 (s, 3H), 0.70 - 0.80 (m, 2H), 0.30 - 0.41 (m, 2H).

Example 39: 2-i3-Chloro-6-(3,4,5-trifluorophenyrspyrroloi3.2-b]pyridin-1 -yll-1 - -fluoroazetidin-1 -vnethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ES!): mass calcd. for Οι ₈ Ηι ₂ 0!Ρ ₄ Ν ₃ 0, 397.1 ; m/z found, 398.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-cfe) δ 8.80 (s, 1 H), 8.33 (s, 1 H), 7.92 - 7.74 (m, 3H), 5.63 - 5.34 (m, 1 H), 5,07 (s, 2H), 4,68 - 4.49 (m, 1 H), 4.44 - 4.17 (m, 2H), 4.08 - 3.87 (m, 1 H).

Example 40: 2-f3-Chloro-6-f4-fluoro-3-(trifluoromethyl)phenyllpyrrolo[3, 2-

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for Ci ₉ H ₁₂ CiF ₆ N ₃ 0, 447.1 ; m/z found, 448.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 8.79 (s, 1 H), 8.32 (s, 1 H), 8.22 - 8.02 (m, 2H), 7.83 (s, 1 H), 7.69 (t, J = 9.7 Hz, 1 H), 5.16 (s, 2H), 4.76 (t, J = 12.5 Hz, 2H), 4.38 (t, J = 12.6 Hz, 2H).

Example 41 : 1 -(Azetidin-1 -yl)-2-f2-methyl-6-(m-tolyl)pyrrolor3,2-blpyridin-1 - yfjethanone.

The title compound was prepared in a manner analogous to Example 31 . MS (ESI): mass calcd. for C ₂ oH ₂ i N ₃ 0, 319.2; m/z found, 320.2 [M+H] ⁺ . H NMR (400 MHz, CDCI ₃ ) δ 8.65 (d, J = 1 .5 Hz, 1 H), 7.62 (s, 1 H), 7.39 - 7.47 (m, 2H), 7.31 - 7.38 (m, 1 H), 7.18 (d, J = 7.3 Hz, 1 H), 6.52 (s, 1 H), 4.73 (s, 2H), 4.05 (t, J = 7.7 Hz, 2H), 3.59 (t, J = 7.7 Hz, 2H), 2.48 (s, 3H), 2.44 (s, 3H), 2.16 (quin, J = 7.8 Hz, 2H). Example 42: 2-(2-Methyl-8-phenyl-pyrroioi3.2-blpyridin-1 -vO-1 -pyrroiidin-1 -yl- ethanone.

The title compound was prepared in a manner analogous to Example 31 . MS (ES!): mass calcd. for C20H21 N ₃ 0, 319,2; m/z found, 320, 1 [M+H] ⁺ . H NMR (400 MHz, CDCI ₃ ) δ 8.60 (br. s., 1 H), 7.59 (d, J = 7.3 Hz, 3H), 7.44 (t, J = 7.6 Hz, 2H), 7.29 - 7.38 (m, 1 H), 6.54 (s, 1 H), 4.81 (s, 2H), 3.48 (td, J = 6.8, 20.0 Hz, 4H), 2.44 (s, 3H), 2.03 (quin, J = 6.7 Hz, 2H), 1 .82 - 1 .92 (m, 2H).

The title compound was prepared in a manner analogous to Example 31 . MS (ES!): mass calcd. for C19H19N3O, 305,2; m/z found, 306,2 [M+H] ⁺ . H NMR (400 MHz, CDCI3) δ 8.69 (s, 1 H), 7.57 - 7.67 (m, 3H), 7.49 (t, J = 7.6 Hz, 2H), 7.34 - 7.43 (m, 1 H), 6.53 (s, 1 H), 5.58 (br. s., 1 H), 4.76 (s, 2H), 2.68 (dt, J = 3.5, 7.1 Hz, 1 H), 2.45 (s, 3H), 0.69 - 0.80 (m, 2H), 0.31 - 0.43 (m, 2H).

The title compound was prepared in a manner analogous to Example 31 . MS (ES!): mass calcd. for C21 H23N3O, 333.2; m/z found, 334.1 [M+H] ⁺ . H NMR (400 MHz, CDCI3) δ 8.81 (s, 1 H), 7.55 (s, 1 H), 7.36 - 7.44 (m, 2H), 7.29 - 7.36 (m, 1 H), 7,15 (d, J = 7.3 Hz, 1 H), 6.52 (s, 1 H), 4.80 (s, 2H), 3.51 (t, J = 6.9 Hz, 2H), 3.43 (t, J = 6.7 Hz, 2H), 2.45 (s, 3H), 2.42 (s, 3H), 2.02 (quin, J = 6.9 Hz, 2H), 1 .87 (quin, J = 6.9 Hz, 2H).

Example 45: 2-[2-Methyl-6-(m-tolyl)pyrrolo[3 _l 2-b]pyridin-1 -yll-1 -morpholino- ethanone.

The title compound was prepared in a manner analogous to Example 31 . MS (ES!): mass calcd. for C21 H23N3O2, 349.2; m/z found, 350.1 [M+H] ⁺ . ¹ H NMR (400 MHz, CDCI3) δ 8.61 (s, 1 H), 7.55 (s, 1 H), 7.36 - 7.44 (m, 2H), 7.29 - 7.36 (m, 1 H), 7.15 (d, J = 7.3 Hz, 1 H), 6.52 (s, 1 H), 4.80 (s, 2H), 3.51 (t, J = 6.9 Hz, 2H), 3.43 (t, J = 6.7 Hz, 2H), 2.45 (s, 3H), 2.42 (s, 3H), 2.02 (quin, J = 8.9 Hz, 2H), 1 .87 (quin, J = 6.9 Hz, 2H).

Example 46: 1 -(Azetidin-1 -yl)-2-[6-(4-fluorophenyl)-2-methyl-pyrrolo[3,2- b]pyridin-1 -yljethanone.

The title compound was prepared in a manner analogous to Example 31 . MS (ES!): mass calcd. for Ci ₉ Hi ₈ FN ₃ 0, 323.1 ; m/z found, 324.2 [M+H] ⁺ . ¹ H NMR (400 MHz, CDCI3) δ 8.58 (br. s., 1 H), 7.66 (s, 1 H), 7,57 (dd, J = 5.29, 8.4 Hz, 2H), 7.16 (t, J = 8.6 Hz, 2H), 6.54 (s, 1 H), 4.75 (s, 2H), 4.07 (t, J = 7.8 Hz, 2H), 3.76 (t, J = 7.6 Hz, 2H), 2.48 (s, 3H), 2.23 (quin, J = 7.8 Hz, 2H). vQethanone.

The title compound was prepared in a manner analogous to Example 31 . MS (ESI): mass calcd. for C19H19N3O, 305,2; m/z found, 306,2 [M+H] ⁺ . H NMR (400 MHz, CDCI3) δ 8.66 (br. s., 1 H), 7.62 (d, J = 8.6 Hz, 3H), 7.46 (t, J =7.6 Hz, 2H), 7.32 - 7.39 (m, 1 H), 6.52 (s, 1 H), 4.72 (s, 2H), 4.05 (t, J = 7.8 Hz, 2H), 3.64 (t, J = 7.7 Hz, 2H), 2.47 (s, 3H), 2.17 (quin, J = 7.8 Hz, 2H).

Example 48: 2-[3-Chloro-6-f3-(trifluoromethyl)phenyllpyrrolo[3 ₁ 2-blpyridin-1 - yll-1 -(3-fluoroazetidin-l -vQethanone.

The title compound was prepared in a manner analogous to Example 1 . MS

(ES!): mass calcd. for Ci9H ₁₄ C!F4N ₃ 0, 41 1 .1 ; m/z found, 412.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-d ₆ ) δ 8.81 (s, 1 H), 8.34 (s, 1 H), 8.08 (s, 2H), 7.94 7.65 (m, 3H), 5.65 - 5.32 (m, 1 H), 5.1 1 (s, 2H), 4.70 - 4.47 (m, 1 H), 4.46 - 4.15 (m, 2H), 4.08 - 3.84 (m, 1 H). EExxaammppllee 4488:: 22--rr33--CChhlloorroo--66--((33,,44,,55--ttrriifflluuoorroo pphheennvyll))ppyyrrrroollooff33,,22--bbllppyyrriiddiinn--11 --vyllll--11 --

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for C ₈ H ₁₁ C!F ₅ N ₃ 0, 415,1 ; m/z found, 416,0 [M+Hf. H NMR (300 MHz, DMSO-cfe) δ 8.81 (s, 1 H), 8.33 (s, 1 H), 7.84 (s, 1 H), 7.81 (dd, J = 9.3, 7.0 Hz, 2H), 5.14 (s, 2H), 4.76 (t, J = 12.4 Hz, 2H), 4.38 (t, J = 12.6 Hz, 2H).

Example 50: 2-r3-Chloro-6-(2,3,4-trifluorophenyl)pyrrolof3,2-blpyridin-1 -yll-1 -

(3,3-difluoroazetidin-1 -yl)ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ES!): mass calcd. for dsHnC!FsNsO, 415,1 ; m/z found, 416,0 [M+Hf. H NMR (300 MHz, DMSO-d ₆ ): 8.58 (s, 1 H), 8.18 (s, 1 H), 7.86 (s, 1 H), 7.57 - 7.41 (m, 2H), 5.14 (s, 2H), 4.75 (t, J = 12.4 Hz, 2H), 4.37 (t, J = 12.5 Hz, 2H).

Example 51 : N-Cvclopropyl-2-f2-methyl-6-(m-tolyl)pyrrolof3 ₁ 2-blpyridin-1 - yllacetamide.

The title compound was prepared in a manner analogous to Example 31 . MS (ES!): mass calcd. for C20H21 N3O, 319.2; m/z found, 320.1 [M+H] ⁺ . H NMR (400 MHz, CDCI3) δ 8.88 (s, 1 H), 7.64 (s, 1 H), 7.32 - 7.47 (m, 3H), 7.21 (d, J = 7.1 Hz, 1 H), 6.52 (s, 1 H), 5.65 (br. s., 1 H), 4.76 (s, 2H), 2.68 (dt, J = 3.5, 7.1 Hz, 1 H), 2.46 (s, 3H), 2.44 (s, 3H), 0.74 (d, J = 5.7 Hz, 2H), 0.38 (dd, J = 1 .0, 3.6 Hz, 2H).

Example 52: 2-(2-Methyl-6-phenyl-pyrroloi3.2-blpyridin-1 -vQ-1 -morpbolino- ethanone.

The title compound was prepared in a manner analogous to Example 31. MS (ESi): mass calcd. for C20H21 N3O2, 335.2; m/z found, 336.1 [M+H] ⁺ . ¹ H NMR (400 MHz, CDCI ₃ ) 6 8.37 (s, 1 H), 7.30 - 7.36 (m, 2H), 7.19 (t, J = 7.6 Hz, 2H), 7.05 - 7.12 (m, 1 H), 6.99 (s, 1 H), 6.29 (s, 1 H), 4.61 (s, 2H), 3.46 (d, J = 4.0 Hz, 4H), 3.38 (d, J = 4.0 Hz, 2H), 3.30 (d, J = 4.4 Hz, 2H), 2.17 (s, 3H).

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for C19H16CIF2N3O, 375.1 ; m/z found, 376.1 [M+H] ⁺ . H NMR (300 MHz, DMSO-d ₆ ) δ 8.72 (s, 1 H), 8.21 (s, 1 H), 7.78 (s, 1 H), 7.57 (s, 1 H), 7.54 (d, J = 8.1 Hz, 1 H), 7.41 (t, J = 7.6 Hz, 1 H), 7.23 (d, J = 7.5 Hz, 1 H), 5.15 (s, 2H), 4.76 (t, J = 12.5 Hz, 2H), 4.38 (t, J = 12.5 Hz, 2H), 2.41 (s, 3H). fluoroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for C19H17CIFN3O, 357.1 ; m/z found, 358.1 [M+H] ^{+ 1} H NMR (300 MHz, DMSO-d ₆ ) δ 8.72 (d, J = 2.0 Hz, 1 H), 8.20 (d, J = 2.0 Hz, 1 H), 7.78 (s, 1 H), 7.60 - 7.49 (m, 2H), 7.40 (t, J = 7.6 Hz, 1 H), 7.23 (d, J = 7. Hz, 1 H), 5.63 - 5.32 (m, 1 H), 5.08 (s, 2H), 4.68 - 4.48 (m, 1 H), 4.44 - 4.16 (m, 2H), 4,08 - 3,86 (m, 1 H), 2.41 (s, 3H).

Example 55: 2-(3-Chloro-6-phenyl-pyrroloi3,2-b]pyridin-1 -yl)-1 -(3,3- difluoroazetidin-1 -yl)ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for Ci8Hi ₄ CiF ₂ N ₃ 0, 361 , 1 ; m/z found, 362, 1 [M+Hf. H NMR (300 MHz, DMSO-cfe) δ 8.74 (s, 1 H), 8.24 (s, 1 H), 7.79 (s, 1 H), 7.76 (d, J = 8.2 Hz, 2H), 7.53 (t, J = 7.5 Hz, 2H), 7.42 (t, J = 7.4 Hz, 1 H), 5.15 (s, 2H), 4.76 (t, J = 12.6 Hz, 2H), 4.38 (t, J = 12,5 Hz, 2H). -(3-Chioro-8-phenyl-pyrroloi3.2-b]pyridiri-1 -vO-1 -(3

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass ca!cd. for Ci8Hi ₅ CiFN ₃ 0, 343.1 ; m/z found, 344.1 [M+Hf. 'H NMR (500 MHz, DMSO-d ₆ ) δ 8.74 (d, J = 1 .9 Hz, 1 H), 8.22 (d, J = 2.0 Hz, 1 H), 7.81 - 7.72 (m, 3H), 7.52 (t, J = 7.6 Hz, 2H), 7.41 (t, J = 7.3 Hz, 1 H), 5.56 - 5.38 (m, 1 H), 5.08 (d, J = 3.0 Hz, 2H), 4.66 - 4.51 (m, 1 H), 4.42 - 4.30 (m, 1 H), 4.30 - 4.19 (m, 1 H), 4.06 - 3.88 (m, 1 H).

Example 57: 2-[3-Chloro-6-(4-fluorophenyl)pyrrolor3,2-blpyridin-1 -νΠ-1 -(3,3 difluoroazetidin-1 -yQethanone.

The title compound was prepared in a manner analogous to Example 1 . S (ESI): mass calcd. for C18H13CIF3N3O, 379.1 ; m/z found, 380.1 [M+H] ⁺ H NMR (300 MHz, D SO-cfe) δ 8.72 (s, 1 H), 8.22 (s, 1 H), 7.87 - 7.71 (m, 2H), 7.79 (s, 1 H), 7.36 (t, J = 8.7 Hz, 2H), 5.14 (s, 2H), 4.76 (t, J = 12.4 Hz, 2H), 4.38 (t, J = 12.6 Hz, 2H). -r3-Chloro-6-(4-fluorophenyl)pyrrolor3.2-blpyridin-1 -yll-1 -(3-

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass ca!cd. for Ci8Hi ₄ CIF ₂ N ₃ 0, 361 .1 ; m/z found, 362, 1 [M+Hf. H NMR (300 MHz, DMSO-d ₆ ) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.21 (d, J = 1 .9 Hz, 1 H), 7.88 - 7.72 (m, 3H), 7.36 (t, J = 8.7 Hz, 2H), 5.62 - 5.32 (m, 1 H), 5.07 (s 2H), 4.66 - 4.49 (m, 1 H), 4,46 - 4.15 (m, 2H), 4.06 - 3.89 (m, 1 H).

Example 59: 3-fr6-(4-Fluoro-2-methyl-phenyl)pyrrolo[3,2-blpyridin-1

yllmethyn-5-methyl-isoxazole.

To a solution of 6-bromo-1 H-pyrrolo[3,2-b]pyridine (300 mg, 1 .5 mmol) in DMF (2 mL), at 0 °C, was added NaH (183 mg, 4.6 mmol, 60% dispersion in oil). The reaction mixture was warmed to room temperature and stirred for 10 minutes and then cooled to 0 °C and 3~(chioromethyl)~5-methyiisoxazoie (240 mg, 1 .8 mmol) was added. The mixture was stirred at 0 °C for 10 minutes then warmed to room temperature and stirred for 4 hours. Water was added and the reaction mixture was extracted with EtOAc. The combined organic layers were dried (MgS0 ₄ ), filtered and evaporated. Purification (FCC, SiO2,0- 100% EtOAc in hexanes) gave the title compound (407 mg, 92%). ^! H NMR (400 MHz, DMSO-C ) δ 8.41 (d, J = 2.0 Hz, 1 H), 8.26 (dd, J = 2.0, 0.9 Hz, 1 H), 7.78 (d, J = 3.4 Hz, 1 H), 6.64 (dd, J = 3.3, 1 .0 Hz, 1 H), 6.07 (d, J = 1 .0 Hz, 1 H), 5.52 (s, 2H), 2.33 (d, J = 0.9 Hz, 3H). Step B: 3-rf6-(4-Fluoro-2-methyl-phenyl)pyrrolor3,2-blpyridin-1 -yllmethyll-5- methyl-isoxazole. In a microwave vial, 3~((6-bromo-1 H-pyrrolo[3,2~b]pyridin-1 ~ yl)methyl)-5-methylisoxazole (50 nig, 0,17 mmol) was dissolved in dioxane (3 mL) followed by the addition of (4-fiuoro~2-methylphenyi)boronic acid (32 mg, 0.21 mmol), Pd(PPh ₃ ) ₄ (19 mg, 0.02 mmol), Na ₂ C0 ₃ (54 mg, 0.51 mmol) and water (3 mL). The microwave vial was caped and the reaction mixture was heated to 70 °C for 14 hours and then cooled to room temperature. DMSO (1 mL) was added and the reaction mixture was filtered, diluted with MeOH and purified by HPLC Method C to give the title compound (23 mg, 42%). MS (ESI): mass calcd. for Ci ₉ H ₁₆ FN ₃ G, 321 .1 ; m/z found, 322.2 [M+H] ⁺ . Ή NMR (400 MHz, DMSO-d ₆ ) δ 8.68 (d, J = 1 .6 Hz, 1 H), 8.57 (s, 1 H), 8.20 (d, J = 3.3 Hz, 1 H), 7.41 (dd, J = 8.5, 8.0 Hz, 1 H), 7.27 (dd, J = 10.2, 2.7 Hz, 1 H), 7.20 (td, J = 8.6, 2.8 Hz, 1 H), 6.87 (dd, J = 3.3, 0.9 Hz, 1 H), 6.19 (d, J = 0.9 Hz, 1 H), 5.72 (s, 2H), 2.34 (s, 3H), 2.28 (s, 3H).

Example 60: 5-Methyl-3-[[6-[3-(trifluorornethyl)phenyllpyrrolo[3,2-b]pyr idin-1 - yllmethynisoxazole.

The title compound was prepared in a manner analogous to Example 59. MS (ESI): mass calcd. for C19H14F3N3O, 357.1 ; m/z found, 358.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-cfe) δ 9,03 (d, J = 1 .8 Hz, 1 H), 8.93 (s, 1 H), 8.20 (s, 1 H), 8.19 - 8.14 (m, 2H), 7.87 - 7.76 (m, 2H), 6.86 (d, J = 3.2 Hz, 1 H), 6,18 (s, 1 H), 5.77 (s, 2H), 2.33 (s, 3H). -Methyl-3-ii8-(m-toiyl)pyrroloi3,2-b]pyridin-1

The title compound was prepared in a manner analogous to Example 59. MS (ESI): mass calcd. for Ci ₉ H ₁₇ N ₃ 0, 303.1 ; m/z found, 304.2 [M÷ } H NMR (400 MHz, DMSO-cfe) δ 8.99 (d, J = 1 .7 Hz, 1 H), 8.93 (s, 1 H), 8.21 (d, J = 3.3 Hz, 1 H), 7.69 (s, 1 H), 7.65 (d, J = 7.9 Hz, 1 H), 7.46 (t, J = 7.6 Hz, 1 H), 7.30 (d, J = 7,5 Hz, 1 H), 6,87 (d, J = 3.2 Hz, 1 H), 6.20 (d, J = 0.8 Hz, 1 H), 5.79 (s, 2H), 2.43 (s, 3H), 2.34 (s, 3H).

Example 62: 5-Methyl-3-ii6-(o-tolyl)pyrroloi3,2-blpyridin-1 -yllmethyllisoxazole irifluoroacetaie salt.

The title compound was prepared in a manner analogous to Example 59. MS (ESI): mass calcd. for C ₉ Hi ₇ N ₃ 0, 303.1 ; m/z found, 304.2 [M+H] ⁺ H NMR (400 MHz, DMSO-de) δ 8.69 (d, J = 1 .6 Hz, 1 H), 8.61 (s, 1 H), 8.22 (d, J = 3.3 Hz, 1 H), 7.42 - 7.34 (m, 4H), 6.88 (dd, J = 3.3, 0.9 Hz, 1 H), 6.19 (d, J = 1 .0 Hz, 1 H), 5.73 (s, 2H), 2.34 (d, J = 0.9 Hz, 3H), 2.27 (s, 3H). Example 63: 3-[f6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-blpyridin-1 - yllmethyn-5-methyl-isoxazole trifiuoroacetate salt.

The title compound was prepared in a manner analogous to Example 59. MS (ES!): mass calcd. for Ci ₉ Hi ₆ FN ₃ 0, 321 .1 ; m/z found, 322.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-ds) δ 8.96 (d, J = 1 .7 Hz, 1 H), 8.89 (s, 1 H), 8.19 (d, J = 3.3 Hz, 1 H), 7.80 (dd, J = 7,3, 2.4 Hz, 1 H), 7.74 - 7.67 (m, 1 H), 7.35 (dd, J = 9.6, 8.6 Hz, 1 H), 6.86 (d, J = 3.3 Hz, 1 H), 6.19 (d, J = 0.9 Hz, 1 H), 5.77 (s, 2H), 2.37 - 2.32 (m, 6H).

Example 64: 3-[f6-(3,5-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yllmethyll-5- methyl-isoxazole trifluoroacetate salt.

TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 5599.. MMSS ( (EESSII)):: mmaassss ccaallccdd.. ffoorr CC1188HH1133FF22NN33OO,, 332255..11 ;; mm//zz ffoouunndd,, 332266..11 [[MM++HH]] ⁺⁺ .. HH NNMMRR ((440000 MMHHzz,, DDMMSSOO--ccfefe)) δδ 99..0000 ((dd,, JJ == 11 ..88 HHzz,, 11 HH)),, 88..8899 ((ss,, 11 HH)),, 88..1144 ((dd,, JJ == 33..33 HHzz,, 11 HH)),, 77..7722 -- 77..6633 ((mm,, 22HH)),, 77..3388 -- 77..2288 ((mm,, 11 HH)),, 66..8833 ((dddd,, JJ == 33..44,, 00..88 HHzz,, 11 HH)),, 66..1188 ((dd,, JJ == 00..99 HHzz,, 11 HH)),, 55..7733 ((ss,, 22HH)),, 22..3333 ((dd,, JJ == 00..88 HHzz,, 33HH))..

iissooxxaazzoollee ttrriifflluuoorrooaacceettaattee ssaalltt..

The title compound was prepared in a manner analogous to Example 59. MS (ES!): mass calcd. for Ci ₈ H _i4 FN ₃ 0, 307.1 ; m/z found, 308.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-cfe) δ 8.95 (s, 1 H), 8.86 (s, 1 H), 8.20 - 8.15 (m, 1 H), 7,93 - 7.85 (m, 2H), 7.48 - 7,37 (m, 2H), 6.88 - 6.83 (m, 1 H), 6.19 (s, 1 H), 5.76 (s, 2H), 2.33 (d, J = 2.1 Hz, 3H). -Cvclobutyl-2-r6-(4-fluoro-3-methyl-phenyl)pyrrolof3,2'

Step A: 6-(4-Fluoro-3-methviphenyl)-1 H-pyrroloi3,2-blpyridine. To a solution a 6~bromo-1 H-pyrrolo[3,2-b]pyridine (2 g, 10.2 mmol) in dioxane (50 mL) was added (4-fluoro-3-methylphenyl)boronic acid (1 .9 g, 12.2 mmol), Pd(dppf)Ci2 (743 mg, 1 .02 mmol), CS2CO3 (9.9 g, 30.5 mmol) and water (5 mL). After 16 hours at 90 °C the reaction mixture cooled and was concentrated under reduced pressure. Purification (FCC, S1O2, 0-100% EtOAc in hexanes) afforded the title compound (1.95 g, 85%). H NMR (400 MHz, DMSO-d ₆ ) δ 1 1 .37 (s, 1 H), 8.59 (d, J = 2.0 Hz, 1 H), 7.93 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.71 - 7.62 (m, 2H), 7.59 - 7.51 (m, 1 H), 7.24 (dd, J = 9.7, 8.5 Hz, 1 H), 6.59 - 6.55 (m, 1 H), 2.33 (d, J = 2.0 Hz, 3H).

Step B: Ethyl 2-(6-(4-Fluoro-3-methylphenyl)-1 H-pyrrolo[3 _l 2-blpyridin-1 - yQacetate. To a solution of 6-(4-fluoro-3-methylphenyl)-1 H-pyrroio[3,2- bjpyridine (1 .5 g, 6.6 mmol) in DMF (60 mL), at 0 °C, was added NaH (371 mg, 9.3 mmol, 60% dispersion in oil). The reaction mixture was warmed to room temperature and stirred for 30 minutes. The reaction mixture was cooled to 0 °C and ethyl 2-bromoacetate (0.77 mL, 7 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 12 hours. Water was added and the mixture was extracted with EtOAc. The combined organic layers were dried (MgSO- , filtered and evaporated. Purification (FCC, SiC ^» 2,0- 50% EtOAc in hexanes) gave the title compound (1 .8 g, 87%). Ή NMR (400 MHz, DMSO-de) δ 8.65 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.0, 0.9 Hz, 1 H), 7.69 (dd, J = 7.7, 2.5 Hz, 1 H), 7.67 (d, J = 3.3 Hz, 1 H), 7.63 - 7.56 (m, 1 H), 7.29 - 7.21 (m, 1 H), 6.62 (dd, J = 3.2, 0.8 Hz, 1 H), 5.24 (s, 2H), 4.16 (q, J = 7.1 Hz, 2H), 2.33 (d, J = 1 .9 Hz, 3H), 1 .22 (t, J = 7.1 Hz, 3H).

Step C: 2-f6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yllacetic acid. To a solution of ethyl 2~(6-(4-Fluoro~3~methylphenyl)~1 H~pyrroio[3,2-b]pyridin~ 1 -yl)acetate (700 mg, 2.2 mmol) in THF (40 rriL) was added LiOH (107 nig, 4.5 mmoi) in water (10 mL) and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was then acidified with 1 N HCI and extracted with EtOAc. The pH of the aqueous layer was adjusted to pH 6 and the product precipitated. The solid was collected via filtration and used crude in the next step (300 mg, 47%). MS (ES!): mass caicd. for C16H13F 2O2, 284.1 ; m/z found, 285.1 [Μ+Η] ^÷ .

Step D: N-Cvclobutyl-2-f6-(4-fluoro-3-methyl-phenyl)pyrrolor3,2-blpy din-1 - yllacetamide trifluoroacetate salt. To a suspension of 2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetic acid (50 mg, 0.18 mmol) and BOP (78 mg, 0.18 mmol) in DCM (3 mL) was added Et ₃ N (73 μΙ_, 0.53 mmol) followed by cyciobutanamine (30 μΙ_, 0.36 mmol). The crude material was purified by HPLC Method C to give the title compound (9 mg, 1 1 %). MS (ESI): mass calcd. for C20H20FN3O, 337,2; m/z found, 338,2 [M+Hj ⁺ , H NMR (600 MHz, DMSO-de) δ 8.88 (d, J = 1 .8 Hz, 1 H), 8.68 (s, 1 H), 8.57 (d, J = 7.7 Hz, 1 H), 8.00 (d, J = 3.3 Hz, 1 H), 7.76 (dd, J = 7.4, 2.4 Hz, 1 H), 7.71 - 7.65 (m, 1 H), 7.33 (t, J = 9.1 Hz, 1 H), 6.77 (d, J = 3.2 Hz, 1 H), 5.06 (s, 2H), 4.25 - 4.13 (m, 1 H), 2.35 (d, J = 1 .8 Hz, 3H), 2.21 - 2.1 1 (m, 2H), 1 .99 - 1 .89 (m, 2H), 1 .71 - 1 .56 (m, 2H).

Example 67: 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll- ^■ pyrrolidin-1 -yl-ethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for C20H20FN3O, 337.2; m/z found, 338.2 [M+H] ^÷ . ¹ H NMR (600 MHz, DMSO-d ₆ ) δ 8.91 (s, 1 H), 8.79 (s, 1 H), 8.01 (d, J = 3.3 Hz, 1 H), 7.80 - 7.75 (m, 1 H), 7.71 - 7,66 (m, 1 H), 7.37 - 7.31 (m, 1 H), 6.81 (d, J = 3.4 Hz, 1 H), 5.35 (s, 2H), 3.65 - 3.57 (m, 2H), 3.36 - 3.30 (m, 2H), 2.35 (s, 3H), 2.03 - 1 .96 (m, 2H), 1 .85 - 1 .79 (m, 2H).

Step A: 3-Bromo-6-(4-fluoro-3-methylphenyl)-1 H-pyrroloi3.2-blpyridine. To a solution of 8-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine (Example 88, Step A, 1 g, 4.4 mmo!) in DMF (45 mL) at room temperature was added NBS (944 mg, 5.3 mmoi). After 1 hour, water was added and the reaction mixture was extracted with 60% EtOAc in hexanes. The combined organic layers were washed with water, dried over gS0 ₄ , filtered and evaporated.

Purification (FCC, SiO2,0~100% EtOAc in hexanes) gave the title compound (1.2 g, 89%). ¹ H N MR (400 MHz, DMSO-d ₆ ) δ 1 1 .78 (s, 1 H), 8.67 (d, J = 2.0 Hz, 1 H), 7.98 (d, J = 1 .9 Hz, 1 H), 7.88 (d, J = 2.9 Hz, 1 H), 7.72 - 7.63 (m, 1 H), 7.62 - 7.53 (m, 1 H), 7.25 (dd, J = 9.7, 8.5 Hz, 1 H), 2.33 (d, J = 1 .9 Hz, 3H).

Step B: 1 -(Azetidin-1 -yi)-2-i3-bromo-6-(4-fluoro-3-methyl-phenyl)pyrroloi3,2- b]pyridin-1 -yllethanone. To a solution of 3-bromo-6-(4-fluoro-3-methyiphenyl)- 1 H-pyrroio[3,2-b]pyridine (200 mg, 0.86 mmol) in DMF (7 mL) at 0 °C was added NaH (37 mg, 0.92 mmol, 60% dispersion in oil). The reaction mixture was warmed to room temperature and stirred for 30 minutes and then cooled to 0 °C followed by the addition of a solution of 1 -(azetidin-1 -yl)-2- bromoethanone (140 mg, 0.78 mmoi) in DMF (3 mL). The reaction mixture was warmed to room temperature and stirred for 12 hours. Water was added and the mixture was extracted with EtOAc. The combined organic layers were dried (MgSC^), filtered and evaporated. Purification (FCC, SiO2,0~100%

EtOAc in hexanes) gave the title compound (178 mg, 68%). MS (ESI): mass caicd. for Ci9H ₁₇ BrFN ₃ 0, 401 .1 ; m/z found, 402.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-de) δ 8.70 (d, J = 1 .8 Hz, 1 H), 8.18 (d, J = 1 .9 Hz, 1 H), 7.80 (s, 1 H), 7.71 - 7.67 (m, 1 H), 7,64 - 7,56 (m, 1 H), 7.28 (dd, J = 9.7, 8,5 Hz, 1 H), 5,02 (s, 2H), 4.24 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.3 i, J = 1 .9 3H), 2.33 - 2.23 (m, 2H).

Example 69: 1 -(Azetidin-1 -yl)-2-f3-fluoro-6-(4-fluoro-3-methyl

phenyl)pyrrolor3,2-blpyridin-1 -vnethanone.

Step A: 3-Bromo-6-(4-fluoro-3-methylphenyl)-1 -((2- (trimethylsilyl)ethoxy)methyl)-1 H-pyrrolo[3,2-blpyridine. To a solution of 3- bromo-6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine (Example 68, Step A, 200 mg, 0.66 mmol) in D F (5 mL) at 0 °C was added NaH (34 mg, 0.85 mmol, 60% dispersion in oil). The reaction mixture was warmed to room temperature and stirred for 30 minutes and then cooled to 0 °C followed by the addition of a solution of (2-(chioromethoxy)ethyi)trimethyisiiane (120 mg, 0.72 mmol) in DMF (3 mL). The reaction mixture was warmed to room temperature and stirred for 12 hours. Water was added and the mixture was extracted with EtOAc. The combined organic layers were dried (MgSO- , filtered and evaporated. Purification (FCC, 810 ₂ ,0-100% EtOAc in hexanes) gave the title compound (166 mg, 58%). H NMR (500 MHz, D!VISO-efe) δ 8.75 (d, J = 1 .9 Hz, 1 H), 8.32 (d, J = 1 .9 Hz, 1 H), 8.07 (s, 1 H), 7.73 - 7.69 (m, 7.64 - 7.59 (m, 1 H), 7.32 - 7.25 (m, 1 H), 5.65 (s, 2H), 3.52 - 3.44 (m, 2H), 2.34 (d, J = 1 .8 Hz, 3H), 0.84 - 0.76 (m, 2H), -0.1 1 (s, 9H).

Step B: 3-Fluoro-6-(4-fluoro-3-methylphenyl)-1 -((2- (trimethyisiiyi)ethoxy)methyi)-1 H-pyrrolof3,2-b1pyridine. To a solution of 3- bromo-6-(4-fiuoro-3-methylphenyi)-1 -((2-(trimethyisiiyl)ethoxy)methyl)-1 H- pyrroio[3,2~b]pyridine (160 mg, 0.34 mmol) in THF (10 mi) at -78 °C was added iBuLi (0.65 mL, 1 .1 mmol, 1 .7M in pentane) and the reaction mixture was stirred at -78 °C for 1 hour. N-fluoro-N-

(phenylsulfonyl)benzenesulfonamide (348 mg, 1 .10 mmol) in THF (2 mL) was added dropwise and the reaction mixture was stirred at -78 °C for 30 minutes, warmed to 0 °C and stirred for 30 minutes. The reaction mixture was poured into water and extracted with EtOAc. The combined organic layers were dried (MgS0 ₄ ), filtered and evaporated. Purification (FCC, SiO ₂ ,0-1 Q0% EtOAc in hexanes) gave the title compound (77 mg, 56%). MS (ESI): mass calcd. for Cao^FaNaOSi, 374.2; m/z found, 375.2 [M+H] ⁺ .

Step C: 3-Fluoro-6-(4-fluoro-3-methylphenyl)-1 H~pyrraiof3,2-blpyridine. To a solution of 3-fluoro-6-(4-fluoro-3-methylphenyl)-1 -((2- (trimethylsilyl)ethoxy)methyl)-1 H-pyrrolo[3,2-b]pyridine (75 mg, 0.2 mmoi) in THF (3 mL) was added TBAF (0.8 mL, 0.8 mmoi, 1 M in THF) and the reaction mixture was heated to 60 °C for 12 hours. Water was added and the reaction mixture was extracted with EtOAc. The combined organic layers were dried ( gS0 ₄ ), filtered and evaporated. Purification (FCC, SiO ₂ ,0-100% EtOAc in hexanes) gave the title compound (29 mg, 59%). MS (ES!): mass calcd. for C 4H10F2N2, 244.1 ; m/z found, 245.1 [M+H] ⁺ .

Step D: 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolor3,2- blpyridin-1 -yllethanone. The title compound was prepared in a manner analogous to Example 68 Step B. MS (ESI): mass calcd. for C19H17F2N3O, 341.1 ; m/z found, 342.2 [M+H] ⁺ . H NMR (600 MHz, CDCI ₃ ) δ 8.69 (s, 1 H), 7.68 (s, 1 H), 7.44 - 7.40 (m, 1 H), 7.40 - 7.36 (m, 1 H), 7.18 (dd, J = 2.6, 1 .1 Hz, 1 H), 7.1 1 {t, J ^~ 8.9 Hz, 1 H), 4.68 (s, 2H), 4.09 (t, J = 7.8 Hz, 2H), 3.92 (t, J = 7.7 Hz, 2H), 2.37 (s, 3H), 2.31 - 2.24 (m, 2H).

The title compound was prepared in a manner analogous to Example 66 Step A through Step C. MS (ESI): mass calcd. for C ₆ Hi ₃ FN ₂ 02, 284.1 ; m/z found, 285.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 13.32 (s, 1 H), 9.06 (s, 1 H), 9.00 (d, J = 1 .7 Hz, 1 H), 8.19 (d, J = 3,3 Hz, 1 H), 7.85 (dd, J = 7.3, 2.4 Hz, 1 H), 7.79 - 7.71 (m, 1 H), 7.36 (dd, J = 9.6, 8.6 Hz, 1 H), 6.89 (d, J = 3.3 Hz, 1 H), 5.35 (s, 2H), 2.35 (d, J = 1 .9 Hz, 3H).

Example 71 : 1 -(azetidin-1 -yl)-2-f6-(2-fluorophenyl)pyrroloi3,2-blpyridin-1 -

Step A: 1 -(Azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolof3,2-b]pyridin-1 -vDethanone.

To a solution of 6-bromo-1 H-pyrrolo[3,2-b]pyridine (1 .5 g, 7.6 mmol) at 0 °C was added NaH (913 mg, 22.8 mmol, 60% dispersion in oil). The reaction mixture was stirred for 30 minutes at rt, then cooled to 0 °C and 1 -(azetidin-1 - yi)~2-bromoethanone (1 .6 g, 9.1 mmol) in DMF (10 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. Water was added and the reaction mixture was extracted with EtOAc. The organics were combined, dried, and concentrated under reduced pressure. Purification (FCC, 0-30% MeOH in DCM) afforded the title compound 1 .39 g, 62%). ¹ H NMR (400 MHz, DMSO-cfe) δ 8.38 (d, J = 2.0 Hz, 1 H), 8.16 (dd, J = 2.0, 1 .0 Hz, 1 H), 7.59 (d, J = 3.3 Hz, 1 H), 6.59 (dd, J = 3.3, 0.9 Hz, 1 H), 4.95 (s, 2H), 4.22 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.33 - 2.22 (m, 2H).

Step B: 1 -(Azetidin-1 -yl)-2-f6-(2-fluorophenyl)pyrrolo[3 ₁ 2-blpyridin-1 - yllethanone. The title compound was prepared in a manner analogous to Example 59, Step B using 1 -(azetidin-1 -yl)-2-(6-bromo- H-pyrrolo[3,2- b]pyridin-1 -yl)ethanone and (2-fiuorophenyl)boronic acid. !VIS (ES!): mass caicd. for C 8H ₆ FN ₃ 0, 309.1 ; m/z found, 310.2 [M+H] ⁺ H NMR (500 MHz, DMSO-de) δ 8.52 - 8.49 (m, 1 H), 8.01 (s, 1 H), 7.64 (d, J = 3.3 Hz, 1 H), 7.60 (td, J = 7.8, 1 .7 Hz, 1 H), 7.48 - 7.42 (m, 1 H), 7.39 - 7.32 (m, 2H), 6.62 (dd, J = 3.2, 0.9 Hz, 1 H), 4.99 (s, 2H), 4.20 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.30 - 2.21 (m, 2H). Example 72: 1 -f Azetidin-1 -yl)-2 6-(3-fluoropheny0pyrrolor3.2-blpyridin-1 ^■ lethar

The title compound was prepared in a manner analogous to Example 71 using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)ethanone and (3-fluoropheny!)boronic acid. MS (ESI): mass calcd, for Ci8Hi ₆ FN ₃ G, 309.1 ; m/z found, 310.2 [M+Hf. H IMMR (500 MHz, DMSO-d ₆ ) δ 8.70 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.65 - 7.60 (m, 3H), 7.58 - 7.51 (m, 1 H), 7.24 - 7.18 (m, 1 H), 6.61 (dd, J = 3.2, 0.9 Hz, 1 H), 5.02 (s, 2H), 4.21 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.32 - 2.22 (m, 2H).

Example 73: 1 -(Azetidin-1 -yl)-2-f6-(p-tolyl)pyrrolof3,2-blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 71 using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)ethanone and p-toiylboronic acid. MS (ESI): mass calcd. for C19H19N3O, 305.2; m/z found, 306.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.65 - 8.60 (m, 1 H), 8.06 (s, 1 H), 7.67 - 7.61 (m, 2H), 7.59 - 7.55 (m, 1 H), 7.34 - 7.28 (m, 2H), 6.60 - 6.56 (m, 1 H), 5.00 (s, 2H), 4.20 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.8 Hz, 2H), 2.36 (s, 3H), 2.30 - 2.21 (m, 2H). -f Azetidin-1 -yl)-2-r6-(3-ethylphenyl)pyrrolof3,2-blpyridin-1 ^■

The title compound was prepared in a manner analogous to Example 71 using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)ethanone and (3-ethylphenyl)boronic acid. MS (ESI): mass calcd. for C20H21 N3O, 319.2; m/z found, 320.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 2.0 Hz, 1 H), 8.08 (dd, J = 2.0, 0.9 Hz, 1 H), 7.61 - 7.52 (m, 3H), 7.41 (t, J = 7.6 Hz, 1 H), 7.23 (d, J = 7.7 Hz, 1 H), 6.60 (dd, J = 3.3, 0.9 Hz, 1 H), 5.01 (s, 2H), 4.20 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.70 (q, J = 7.6 Hz, 2H), 2.31 - 2.21 (m, 2H), 1 .25 (t, J = 7.6 Hz, 3H).

Example 75: N-Cyclopropyl-2-[6-(2-fluorophenyl)pyrrolo[3,2-blpyridin-1 -

Step A: 2-(6-Bromo-1 H-pyrrolof3,2-blpyridin-1 -yl)-N-cyclopropylacetamide. To a solution of 6-bromo-1 H-pyrrolo[3,2-b]pyridine (1 g, 5.0 mmol) in DMF (20 ml_) at 0 °C was added NaH (284 mg, 7.1 mmol, 60% dispersion in oil). The reaction mixture was stirred for 30 minutes and 2-bromo-N- cyclopropylacetamide (1 .08 g, 6.1 mmol) in DMF (5 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. Water was then added and the reaction mixture was extracted with 60% EtOAc in hexanes. The combined organic layers were dried (MgS0 ₄ ), filtered and evaporated. Purification (FCC, 810 ₂ ,0-100% EtOAc in hexanes) gave the title compound (1 .21 g, 81 %). H NMR (400 MHz, DMSO-d ₆ ) δ 8.38 (d, J = 2.1 Hz, 1 H), 8.31 (d, J = 4.3 Hz, 1 H), 8.12 (dd, J = 2.0, 0.9 Hz, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 6.59 (dd, J = 3.3, 0.9 Hz, 1 H), 4.81 (s, 2H), 2.69 -

2.60 (m, 1 H), 0.67 - 0.60 (m, 2H), 0.47 - 0.41 (m, 2H).

Step B: N-Cvclopropyl-2-f6-(2-fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yllacetamide. The title compound was prepared in a manner analogous to Example 59, Step B. MS (ES!): mass caicd. for Ci ₃ Hi ₆ FN ₃ 0, 309.1 ; m/z found, 310.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.50 (t, J = 2.0 Hz, 1 H), 8.34 (d, J = 4.3 Hz, 1 H), 7.96 (s, 1 H), 7.66 (d, J = 3.2 Hz, 1 H), 7.60 (td, J = 7.8, 1 .7 Hz, 1 H), 7.48 - 7,41 (m, 1 H), 7.39 - 7.31 (m, 2H), 6.61 (dd, J = 3.3, 0.9 Hz, 1 H), 4.85 (s, 2H), 2.68 - 2.59 (m, 1 H), 0.66 - 0.58 (m, 2H), 0.46 - 0.39 (m, 2H).

The title compound was prepared in a manner analogous to Example /5. MS (ESi): mass calcd. for CisHieFNsO, 309.1 ; m/z found, 310.2 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-ds) δ 8.70 (d, J = 2.0 Hz, 1 H), 8.34 (d, J = 4.2 Hz, 1 H), 8.17 - 8.14 (m, 1 H), 7.66 (d, J = 3.3 Hz, 1 H), 7.64 - 7.58 (m, 2H), 7.58 - 7.50 (m, 1 H), 7.24 - 7.17 (m, 1 H), 6.60 (d, J = 3.3 Hz, 1 H), 4.88 (s, 2H), 2.69 - 2.60 (m, 1 H), 0.67 - 0.60 (m, 2H), 0.47 - 0.41 (m, 2H).

Example 77: N-Cyclopropyl-2-[6-(p-tolyl)pyrroloi3,2-blpyridin-1 -yllacetamide.

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C19H19N3O, 305.2; m/z found, 306.2 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8,63 (d, J = 2.0 Hz, 1 H), 8.34 (d, J = 4.2 Hz, 1 H), 8.03 (dd, J = 2.0, 0.9 Hz, 1 H), 7.66 - 7.58 (m, 3H), 7.34 - 7,28 (m, 2H), 6.57 (dd, J = 3.2, 0.8 Hz, 1 H), 4.86 (s, 2H), 2.70 - 2.59 (m, 1 H), 2.36 (s, 3H), 0.67 - 0.59 (m, 2H), 0.47 - 0.40 (m, 2H). Example 78: 2-(6-Phenvipyrrolo[3,2-b]pyridin-1 -yl)-1 -pyrrolidin-1 -yl-ethanone.

Step A: 2-(6-Bromo-1 H-pyrroto[3,2-blpyridin-1 -yl)-1 -(pyrrolidin-1 -vDethanone. To a solution of 6-bromo-1 H-pyrrolo[3,2-b]pyridine (1 g, 5.0 mmo!) in DMF (20 mL) at 0 °C was added NaH (284 mg, 7.1 mmol, 60% dispersion in oil). The reaction mixture was stirred for 30 minutes and 2-bromo-1 -(pyrrolidin-1 - yl)ethanone (1 .02 g, 5.3 mmol) in DMF (5 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. Water (1 mL) was added and the reaction mixture was concentrated onto silica gel. Purification (FCC, S1O2, 0-20% MeOH in EtOAc) gave the title compound (quant, yield). ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.37 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.1 , 0.8 Hz, 1 H), 7.58 (d, J = 3.3 Hz, 1 H), 6.58 (dd, J = 3.3, 0.8 Hz, 1 H), 5.12 (s, 2H), 3.56 (t, J = 6.8 Hz, 2H), 3.37 - 3.25 (m, 2H), 2.01 - 1 .90 (m, 2H), 1 .86 - 175 (m, 2H).

Step B: 2-(6-Phenylpyrroioi3,2-blpyridin-1 -yl)-1 -pyrroiidin-1 -yl-ethanone. The title compound was prepared in a manner analogous to Example 59, Step B, MS (ESI): mass calcd. for C19H13N3O, 305.2; m/z found, 306.2 [M+H] ⁺ . ¹ H NMR (600 MHz, DMSO-d ₆ ) δ 8.66 - 8,62 (m, 1 H), 8.12 - 8.10 (m, 1 H), 7.77 - 7.71 (m, 2H), 7.61 - 7.56 (m, 1 H), 7.53 - 7.46 (m, 2H), 7.40 - 7.34 (m, 1 H), 6.60 - 6.57 (m, 1 H), 5.17 (s, 2H), 3.62 - 3.56 (m, 2H), 3.35 - 3.30 (m, 2H), 2.01 - 1 .92 (m, 2H), 1 .85 - 1 .76 (m, 2H). Example 79: 2-r6-(2-Fluoropheny0pyrrolor3.2-blpyridin-1 -yll-1 -pyrrolidin-1 -yl- ethanone.

The title compound was prepared in a manner analogous to Example 78. MS (ESI): mass calcd. for C19H18FN3O, 323.1 ; m/z found, 324.2 [M+H] ^{+ 1} H NMR (600 MHz, DMSO-C ) δ 8.49 (s, 1 H), 8.01 (s, 1 H), 7.63 (d, J = 3.4 Hz, 1 H), 7.61 - 7.56 (m, 1 H), 7.48 - 7.41 (m, 1 H), 7.38 - 7.30 (m, 2H), 6.63 - 6.60 (m, 1 H), 5.16 (s, 2H), 3.61 - 3.53 (m, 2H), 3.34 - 3.30 (m, 2H), 1 .98 - 1.92 (m, 2H), 1 .83 - 1 .76 (m, 2H).

Example 80: 2-r6-(4-FluorophenvDpyrrolor3.2-blpyridin-1 -yll-1 -pyrrolidin-1 -yl- ethanone.

The title compound was prepared in a manner analogous to Example 78. MS

(ES!): mass calcd. for Ci9H ₁₈ FN ₃ 0, 323.1 ; m/z found, 324.2 [M+H] ^{+ 1} H NMR (600 MHz, DMSO-ofe) δ 8.63 - 8.61 (m, 1 H), 8.10 (s, 1 H), 7.80 - 7.73 (m, 2H), 7.60 - 7.57 (m, 1 H), 7.36 - 7.29 (m, 2H), 6.60 - 6.57 (m, 1 H), 5.17 (s, 2H), 3.59 (t, J = 6.9 Hz, 2H), 3.32 (t, J = 7.0 Hz, 2H), 1 .99 - 1 .93 (m, 2H), 1 .84 - 1 .77 (m, 2H). Example 81 : 2-r6-(m-Tolyl)pyrrolor3,2-blpyridin-1 -yll-1 -pyrrolidir¾-1 -yl

ethanone

The title compound was prepared in a manner analogous to Example 78. MS (ESi): mass calcd. for C20H21 N ₃ 0, 319,2; m/z found, 320,2 [M+H] ⁺ . H NMR (600 MHz, DMSO-ofe) δ 8.63 (dd, J = 2.0, 0.9 Hz, 1 H), 8.10 - 8.07 (m, 1 H),

7.58 (dd, J = 3.2, 0.9 Hz, 1 H), 7.55 (s, 1 H), 7.52 (d, J = 7.9 Hz, 1 H), 7.38 (t, J = 7.6 Hz, 1 H), 7.19 (d, J = 7.5 Hz, 1 H), 6.58 (d, J = 3,2 Hz, 1 H), 5, 17 (s, 2H),

3.59 (t, J = 6.9 Hz, 2H), 3.33 (t, J = 6.9 Hz, 2H), 2.40 (s, 3H), 1 .99 - 1 .94 (m, 2H), 1 .84 - 1 .77 (m, 2H).

Example 82: 2-[6-(p-Tolyl)pyrrQio[3,2-b pyridin-1 -yl]-1 -pyrrolidin-1 -yl- ethanone.

The title compound was prepared in a manner analogous to Example 78. MS (ESI): mass calcd. for C ₂₀ H ₂ i N ₃ O, 319.2; m/z found, 320.2 [M+H] ⁺ H NMR (600 MHz, DMSO-de) δ 8,64 - 8.60 (m, 1 H), 8.07 (s, 1 H), 7.65 - 7.61 (m, 2H), 7.56 (dd, J = 3.2, 1 ,0 Hz, 1 H), 7.30 (d, J = 8.3 Hz, 2H), 6.58 - 6.55 (m, 1 H), 5.16 (s, 2H), 3.59 (t, J = 6.9 Hz, 2H), 3.32 (t, J = 7.0 Hz, 2H), 2.36 (s, 3H), 2.00 - 1 .92 (m, 2H), 1 ,84 - 1 .76 (m, 2H). Example 83: 2-r6-(3-Ethylphenyl)pyrrolo[3,2-blpyridin-1 -yll-1 -pyrrolidiri-1 -yl- ethanone.

The title compound was prepared in a manner analogous to Example 78. MS (ESI): mass calcd. for C21H23N3O, 333,2; m/z found, 334,2 [M+H] ⁺ . H NMR (600 MHz, DMSO-C ) δ 8.64 - 8.62 (m, 1 H), 8.09 - 8.07 (m, 1 H), 7.59 - 7.51 (m, 3H), 7.42-7.38 (m, 1H), 7.22 (d, J = 7.1 Hz, 1H), 6.59-6.57 (m, 1H), 5.17 (s, 2H), 3.59 (t, J = 6.9 Hz, 2H), 3.32 (t, J = 7.0 Hz, 2H), 2.70 (q, J = 7.6 Hz, 2H), 2.00 - 1.94 (m, 2H), 1.84 - 1.77 (m, 2H), 1.27 - 1.22 (m, 3H).

Example 84: 2-r6-(3-FluorophenvDpyrrolor3.2-blpyridin-1 -yll-1 -pyrrolidin-1 -yl- ethanone.

The title compound was prepared in a manner analogous to Example 78. MS

(ES!): mass calcd. for C19H18FN3O, 323.1; m/z found, 324.2 [M+H] ^{+ 1} H NMR (600 MHz, DMSO-ofe) δ 8.70 - 8.68 (m, 1H), 8.20-8.17 (m, 1H), 7.64-7.58 (m, 3H), 7.56-7.50 (m, 1H), 7.23-7.17 (m, 1H), 6.62-6.58 (m, 1H), 5.18 (s, 2H), 3.59 (t, J = 6.8 Hz, 2H), 3.33 (t, J = 6.9 Hz, 2H), 2.00 - 1.94 (m, 2H), 1.85-1.77 (m, 2H).

Example 85: 1 -Morpholino-2-(6-phenylpyrroloi3,2-blpyridin-1 -yPethanone.

Step A: 2-(6-Bromo-1 H-pyrrolQf3.2-b]pyridin-1 -yl)-1 -morpholinoethanone. The title compound was prepared in a manner analogous to Example 78, Step A substituting 2-bromo-l -morpholinoethanone for 2-bromo-1 -{pyrrolidin-1 - yi)ethanone. ¹ H NMR (500 MHz, DMSO~d ₆ ) δ 8.37 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.58 (d, J = 3.3 Hz, 1 H), 6.59 (dd, J = 3.3, 0.9 Hz, 1 H), 5.24 (s, 2H), 3.69 (t, J = 4.8 Hz, 2H), 3.60 (t, J = 4.9 Hz, 2H), 3.54 (t, J = 4.8 Hz, 2H), 3.44 (t, J = 4.8 Hz, 2H).

Step B: 1 -Morpholino-2-(6-phenylpyrroloi3,2-b]pyridin-1 -vDethanone. The title compound was prepared in a manner analogous to Example 78, Step B. MS (ES!): mass calcd. for C19H19N3O2, 321 .1 ; m/z found, 322.2 [M+H] ⁺ . ¹ H NMR (600 MHz, DMSO-ds) δ 8.65 (s, 1 H), 8.1 1 (s, 1 H), 7.76 - 7.70 (m, 2H), 7.61 - 7.56 (m, 1 H), 7.54 - 7.47 (m, 2H), 7.41 - 7.35 (m, 1 H), 6.59 (s, 1 H), 5.31 (s, 2H), 3.70 (s, 2H), 3.59 (s, 4H), 3.44 (s, 2H).

The title compound was prepared in a manner analogous to Example 85. MS (ES!): mass calcd. for Ci9Hi ₈ F ₃ O ₂ , 339.1 ; m/z found, 340.2 [M+H] ⁺ . ¹ H NMR (600 MHz, DMSO-ds) δ 8.50 - 8.48 (m, 1 H), 8.02 - 8.00 (m, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 7.59 (td, J = 7.8, 1 .7 Hz, 1 H), 7.48 - 7.42 (m, 1 H), 7.38 - 7.32 (m, 2H), 6.62 (dd, J = 3.2, 0.8 Hz, 1 H), 5.29 (s, 2H), 3.70 - 3.65 (m, 2H), 3.60 - 3.55 (m, 4H), 3.43 (t, J = 5,0 Hz, 2H). Example 87: 2-f6-(3-FluQrQphenyDpyrroiQf3.2-b]pyridin-1 -yll-1 -morpholino ethanone.

The title compound was prepared in a manner analogous to Example 85. MS (ESI): mass ca!cd. for C19H18FN3O2, 339.1 ; m/z found, 340.2 [M+H] ⁺ . H NMR (600 MHz, DMSO-efe) δ 8.89 (d, J = 2.0 Hz, 1 H), 8.18 (s, 1 H), 7.65 - 7.58 (m, 3H), 7.57 - 7.50 (m, 1 H), 7.24 - 7.17 (m, 1 H), 6.60 (dd, J = 3.3, 0.8 Hz, 1 H), 5.30 (s, 2H), 3.75 - 3.68 (m, 2H), 3.62 - 3.56 (m, 4H), 3.47 - 3.41 (m, 2H). Example 88: 2-[6-(4-Fluorophenyl)pyrroioi3.2-blpyridin-1 -yll-1 -morpholino- ethanone.

The title compound was prepared in a manner analogous to Example 85. MS (ES!): mass calcd. for C19H18FN3O2, 339.1 ; m/z found, 340.2 [M+H] ⁺ . ^! H NMR (600 MHz, DMSO-cfe) δ 8.64 - 8.60 (m, 1 H), 8.10 (s, 1 H), 7.80 - 7.74 (m, 2H), 7.60 - 7.57 (m, 1 H), 7.37 - 7.30 (m, 2H), 6.61 - 6.58 (m, 1 H), 5.30 (s, 2H), 3.72 - 3.68 (m, 2H), 3.61 - 3.55 (m, 4H), 3.47 - 3.41 (m, 2H).

The title compound was prepared in a manner analogous to Example 85. MS (ES!): mass calcd. for C20H21 N3O2, 335.2; m/z found, 336.2 [M+H] ⁺ . ¹ H HMR (600 MHz, DMSO-ds) δ 8.63 (s, 1 H), 8.08 (s, 1 H), 7.58 (dd, J = 3.3, 0.9 Hz, 1 H), 7.55 (s, 1 H), 7.52 (d, J = 7.7 Hz, 1 H), 7.38 (t, J = 7,5 Hz, 1 H), 7.19 (d, J = 7.5 Hz, 1 H), 6.59 (d, J = 3.2 Hz, 1 H), 5.30 (s, 2H), 3.73 - 3.67 (m, 2H), 3.62 - 3.56 (m, 4H), 3.47 - 3.42 (m, 2H), 2.40 (s, 3H). -Morpholino-2-[6-(p-tolyl)pyrrolof3,2-blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 85. MS (ES!): mass calcd. for C ₂₀ H ₂ i N ₃ O ₂ , 335.2; m/z found, 336.2 [M+H] ⁺ . ¹ H HMR (600 MHz, DMSO-d ₆ ) δ 8.64 - 8.60 (m, 1 H), 8.07 (s, 1 H), 7.65 - 7.61 (m, 2H), 7.58 - 7.55 (m, 1 H), 7.33 - 7.28 (m, 2H), 6.58 (d, J = 3.1 Hz, 1 H), 5.29 (s, 2H), 3.72 - 3.66 (m, 2H), 3.62 - 3.55 (m, 4H), 3.46 - 3.41 (m, 2H), 2.36 (s, 3H).

The title compound was prepared in a manner analogous to Example 85. MS (ES!): mass calcd. for C21 H23N3O2, 349.2; m/z found, 350.2 [M+H] ⁺ . ¹ H HMR (600 MHz, DMSO-ds) δ 8.66 - 8.59 (m, 1 H), 8.07 (s, 1 H), 7.60 - 7.51 (m, 3H), 7.41 (t, J = 7.6 Hz, 1 H), 7.23 (d, J = 7.6 Hz, 1 H), 6.59 (d, J = 3.3 Hz, 1 H), 5.31 (s, 2H), 3.72 - 3.67 (m, 2H), 3.62 - 3.56 (m, 4H), 3.46 - 3.42 (m, 2H), 2.74 - 2.66 (m, 2H), 1 .25 (t, J = 7.6 Hz, 3H). νΠ-Ν,Ν-dimethyl-acetamide.

To a solution of 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N,N- dimethylacetamide (Intermediate 15, 88 mg, 0.22 mmol) in dioxane (1 mL) was added (4-fluoro-3-methylphenyl)boronic acid (419 mg, 0.27 mmol),

Pd(dppf)CI ₂ (16.6 mg, 0.203 mmol), Cs ₂ C0 ₃ (221 mg, 0.68 mmol). After 16 hours at 90 °C the reaction mixture cooled and was concentrated under reduced pressure. Purification (FCC, SiOa, 0-20% MeOH in EtOAc) afforded the title compound (37 mg, 50%). MS (ESI): mass calcd. for C18H17F2N3O, 329.1 ; m/z found, 330.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.66 (d, J = 1 .8 Hz, 1 H), 8.17 - 8.12 (m, 1 H), 7,68 (dd, J = 7.6, 2.4 Hz, 1 H), 7.62 - 7,55 (m, 2H), 7.27 (dd, J = 9.6, 8.5 Hz, 1 H), 5.20 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H), 2.33 (d, J = 1 .9 Hz, 3H).

Example 93: 2-[6-(3,4-Difluorophenyl)-3-fluoro-pyrrolo[3,2-blpyridin-1 -vn-N,N- dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 92 using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N,N- dimethylacetamide (Intermediate 15) and (3,4-difiuorophenyl)boronic acid. MS (ESI): mass calcd. for C ₇ H ₁₄ F ₃ N ₃ 0, 333.1 ; m/z found, 334.0 +Hf. Ή NMR (400 MHz, DMSO-cfe) δ 8.74 - 8.70 (m, 1 H), 8.27 - 8.22 (m, 1 H), 7.88 (ddd, J = 12.3, 7.8, 2.3 Hz, 1 H), 7.68 - 7.52 (m, 3H), 5,20 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H).

Example 94: 2-i3-Fluoro-6-(3 _l 4,5-trifluQrophenyl)pyrroloi3 _l 2-blpyridin-1 -γΠ~ -dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 92 using 2-(6~bromo~3-fluoro~1 H-pyrroio[3,2~b]pyridin-1 ~yl)-IM,N- dimethylacetamide (Intermediate 15) and (2,3,4-trifluorophenyl)boronic acid. MS (ESI): mass caicd. for C17H13F4N3O, 351 .1 ; m/z found, 352.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.77 (d, J = 1 .9 Hz, 1 H), 8.30 (t, J = 2.2 Hz, 1 H), 7.85 - 7.79 (m, 2H), 7,67 (d, J = 2.2 Hz, 1 H), 5.21 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H). -[6-f3-(Difluoromethyl)phenyl1-3-fluoro-pyrrolof3,2-blpyridi n-1 -

The title compound was prepared in a manner analogous to Example 92 using 2-(6~bromo~3-fluoro~1 H-pyrrolo[3,2~b]pyridin-1 ~yl)-IM,N- dimethylacetarnide (Intermediate 15) and (3-(difluoromethyl)phenyl)boronic acid. MS (ESI): mass caicd. for C18H16F3N3O, 347.1 ; m/z found, 348.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.27 - 8.23 (m, 1 H), 7.94 (s, 2H), 7.71 - 7.58 (m, 3H), 7.12 (t, J = 55.8 Hz, 1 H), 5.24 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H). -r3-Fluoro-6-(4-methyl-2-thienyl)pyrrolor3,2-blpyridin-1-vn- N,N-

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fluoro-1H-pyrroio[3,2-b]pyridin-1-yl)-N,N- dimethylacetamide (Intermediate 15) and 4,4,5,5~tetramethyl~2-(4- methyltbiophen-2-yi)-1 ,3,2-dioxaborolane. MS (ESI): mass calcd, for

C ₁₆ H _l6 FN ₃ OS, 317.1; m/z found, 318.0 [M+H] ⁺ . H MR (400 MHz, DMSO-c ₆ ) 68,64 (d, J = 1.9 Hz, 1H), 8.13-8.09 (m, 1H), 7.59 (d, J = 2.2 Hz, 1H), 7.42 (d, J = 1.4 Hz, 1H), 7.18-7.14(m, 1H), 5.19 (s, 2H), 3.10 (s, 3H), 2.86 (s, 3H), 2.26 (s, 3H). -[6-(5-Chloro-2-thienyl)-3-fluoro-pyrrolor3,2-blpy din-1-yll-N,N-

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fluoro-1H-pyrrolo[3,2-b]pyridin-1-yl)-N,N- dimethylacetamide (Intermediate 15) and (5-chlorothiophen-2-yl)boronic acid. MS (ESI): mass calcd. for Ci ₅ H ₁₃ CIFN ₃ OS, 337.0; m/z found, 338.0 [M+H] ⁺ . !H NMR(400MHz, DMSO-d ₆ ) δ 8.65 (d, J= 1.9 Hz, 1H), 8.14 (t, J = 2.2 Hz, 1 H), 7.64 (d, J = 2.3 Hz, 1 H), 7.47 (d, J = 3.9 Hz, 1 H), 7.22 (d, J = 4.0 Hz, 1H), 5.20 (s, 2H), 3.10 (s, 3H), 2.86 (s, 3H). -r3-Fluoro-6-(4-fluorophenyl)pyrrolo[3,2-blpyridin-1 -yl1-N,N-

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fluoro-1 H-pyrroio[3,2-b]pyridin-1 -yl)-N,N- dimethylacetamide (Intermediate 15) and (4-fluorophenyl)boronic acid. MS (ESI): mass calcd. for C17H15F2N3O, 315.1 ; m/z found, 316.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.69 - 8.65 (m, 1 H), 8.20 - 8.16 (m, 1 H), 7.83 - 7.76 (m, 2H), 7.64 - 7.60 (m, 1 H), 7.40 - 7.30 (m, 2H), 5.21 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H).

Example 99: N-Cyclopropyl-2-f6-[5-(trifluoromethyl)-3-pyridvnpyrrolof3,2 - b]pyridin-1 -yllacetamide.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N-cyclopropylacetamide

(intermediate of Step A, Example 75) and (5-(trifluoromethyi)pyridin-3~ yl)boronic acid, MS (ESI): mass calcd, for C18H-15F3N4O, 360.1 ; m/z found, 361 .2 [M+Hf. ¹ H NMR (500 MHz, CD ₃ OD) δ 9.16 (d, J = 2.1 Hz, 1 H), 8.88 (s, 1 H), 8.68 (d, J = 1 .9 Hz, 1 H), 8.47 (s, 1 H), 8.24 - 8.22 (m, 1 H), 7.64 (d, J = 3.3 Hz, 1 H), 6.70 (d, J = 3.2 Hz, 1 H), 4.95 (s, 2H), 2.73 - 2.66 (m, 1 H), 0.76 - 0.69 (m, 2H), 0.56 - 0.50 (m, 2H). -Cvclopropyl-2-i6-(3,4-difiuorophenvnpyrroloi3,2-b]pyridir¾ -1 -

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolofS^-bjpyndin-l -y -N-cyclopropylacetamide (intermediate of Step A, Example 75) and (3,4-difiuorophenyi)boronic acid, MS (ESI): mass calcd. for C-isHisFaNaG, 327.1 ; m/z found, 328.2 [M+Hf. ¹ H NMR (500 MHz, CD ₃ OD) δ 8.55 (d, J = 1 .9 Hz, 1 H), 8.03 - 8.01 (m, 1 H), 7.84 - 7.58 (m, 1 H), 7.57 (d, J = 3.3 Hz, 1 H), 7.50 - 7.45 (m, 1 H), 7.40 - 7.33 (m, 1 H), 6.67 - 6.65 (m, 1 H), 4.90 (s, 2H), 2.72 - 2.66 (m, 1 H), 0.75 - 0,69 (m, 2H), 0.54 - 0.49 (m, 2H).

Example 101 : N-Cyclopropyl-2-[6-i4-fluoro-3- (trifluoromethynphenynpyrrolo[3,2-b]pyridin-1 -ynacetamide.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N-cyclopropylacetamide (intermediate of Step A, Example 75) and (4-fluoro-3- (trifluoromethyl)phenyl)boronic acid. MS (ESI): mass calcd. for C19H15F4N3O, 377.1 ; m/z found, 378.2 [M+H] ⁺ . ¹ H IMMR (500 MHz, CD ₃ OD) δ 8.58 (d, J =

1 .9 Hz, 1 H), 8.07 (s, 1 H), 8.00 - 7.94 (m, 2H), 7.59 (d, J = 3.3 Hz, 1 H), 7.45 (t, J = 9.6 Hz, 1 H), 6,67 (d, J = 3,3 Hz, 1 H), 4.92 (s, 2H), 2.73 - 2.66 (m, 1 H), 0.77 - 0.69 (m, 2H), 0,55 - 0,49 (m, 2H). -(Azetidin-1 -yl)-2-f6-r5-(trifluoromethyl)-3-pyridvnpyrrolor3.2-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)ethanone (Intermediate 14) and (5-(trifiuoromethyl)pyridin~3~yl)boronic acid. MS (ESI): mass calcd. for dsH^Fs^O, 360.1 ; m/z found, 361 ,2 [M+H] ⁺ . H NMR (500 MHz, CD ₃ OD) 6 9.16 (d, J = 2.1 Hz, 1 H), 8.87 (s, 1 H), 8.67 (d, J = 1 .9 Hz, 1 H), 8.47 (s, 1 H), 8.24 (s, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 6.69 (d, J = 3.3 Hz, 1 H), 5.03 (s, 2H), 4.30 (t, J = 7.8 Hz, 2H), 4.06 (t, J = 7.8 Hz, 2H), 3.33 - 3.29 (m, 2H).

Exam le 103: 1 -(Azetidin-1 -yl)-2-[6-(3,4-difluorophenyl)pyrrolof3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(azetidin-1 ~yi)-2~(6~bromo-1 H-pyrrolo[3,2~b]pyridin~1 -yl)ethanone (Intermediate 14) and (3,4-dif!uoropheny!)boronic acid. MS (ESI): mass calcd for C ₈ H ₁₅ F ₂ N ₃ 0, 327.1 ; m/z found, 328.2 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.55 (d, J = 1 .9 Hz, 1 H), 8.05 - 8.03 (m, 1 H), 7,66 - 7.59 (m, 1 H), 7.56 (d, J = 3.3 Hz, 1 H), 7.51 - 7.46 (m, 1 H), 7.39 - 7.32 (m, 1 H), 6.66 (dd, J = 3.3, 0.9 Hz, 1 H), 4.98 (s, 2H), 4.26 (t, J = 7.7 Hz, 2H), 4.05 (t, J = 7.8 Hz, 2H), 2.40 - 2.31 (m, 2H). -(Azetidin-1 -yl)-2 6 4-fluoro-3'

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 ~(azetidin~1 -yl)~2-(6-bromo~1 H~pyrrolo[3,2-b]pyridin-1 ~yl)ethanone (Intermediate 14) and 4-fluoro-3-(trifluoromethyl)phenyl)boronic acid . MS (ESI): mass calcd. for C ₉ H ₁₅ F4N ₃ 0, 377.1 ; m/z found, 378.2 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 8.09 - 8.07 (m, 1 H), 7,98 - 7.90 (m, 2H), 7.56 (d, J = 3.3 Hz, 1 H), 7.45 - 7.39 (m, 1 H), 6.66 (dd, J = 3.3, 0.9 Hz, 1 H), 4.98 (s, 2H), 4.26 (t, J = 7.7 Hz, 2H), 4.05 (t, J = 7.8 Hz, 2H), 2.40 - 2.30 (m, 2H).

yll-1 -pyrrolidin-1 -yl-ethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrroio[3,2-b]pyridin-1 -yl)-1 -(pyrroiidin-1 -yl)ethanone (Intermediate 10) and (4-fluoro-3-(trifluoromethyl)phenyl)boronic acid.

Purification by HPLC Method A gave the title compound (35 mg, 27%). MS (ESI): mass calcd. for C20H17F4N3O, 391 .1 ; m/z found, 392.2 [M+H] ⁺ . ^! H NMR (400 MHz, CD ₃ OD) 5 8.57 (d, J = 1 .9 Hz, 1 H), 8.13 - 8.1 1 (m, 1 H), 8.01 - 7.94 (m, 2H), 7.58 (d, J = 3,3 Hz, 1 H), 7.48 - 7.40 (m, 1 H), 6.68 (dd, J = 3,3, 0.9 Hz, 1 H), 5.19 (s, 2H), 3.65 (t, J = 6.8 Hz, 2H), 3.46 (t, J = 6.9 Hz, 2H), 2.12 - 2.02 (m, 2H), 1 .97 - 1 .87 (m, 2H). -(3,3-Difluoroazetidin-1 -yl)-2-f6-f4-fluoro-3'

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3,3-difluoroazetidin-1 - yi)ethanone (Intermediate 12) and (4~fiuoro~3-(trifluoromethyi)phenyi)boronic acid, MS (ESI): mass calcd. for C 9H13F6N3O, 413, 1 ; m/z found, 414,2 [M+H] ^{+ 1} H NMR (400 MHz, CD ₃ OD) δ 8.62 - 8.59 (m, 1 H), 8.16 - 8.13 (m, 1 H), 8.03 - 7.96 (m, 2H), 7.61 - 7.58 (m, 1 H), 7.50 - 7.42 (m, 1 H), 6.71 - 6.68 (m, 1 H), 5.14 (s, 2H), 4.67 (t, J = 12,0 Hz, 2H), 4.41 (t, J = 12.2 Hz, 2H).

Example 107: 2-f6-(3.4-Difluorophenyl)pyrrolor3,2-blpyridin-1 -yll-1 - morpholino-ethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2~(6~bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -morpholinoethanone (Intermediate 1 1 ) and (3,4-difluorophenyi)boronic acid. Purification by HPLC Method A gave the title compound (21 mg, 38%). MS (ESI): mass calcd. for C19H17F2N3O2, 357.1 ; m/z found, 358.2 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 8.07 - 8,05 (m, 1 H), 7,63 (ddd, J = 12.0, 7.6, 2,3 Hz, 1 H), 7.55 (d, J = 3.3 Hz, 1 H), 7.52 - 7.47 (m, 1 H), 7.41 - 7.32 (m, 1 H), 6.67 (dd, J = 3.3, 0.8 Hz, 1 H), 5.28 (s, 2H), 3.80 - 3.74 (m, 2H), 3.72 - 3.63 (m, 4H), 3.61 - 3.55 (m, 2H). -r6-f4-Fluoro-3-(trifluoromethyl)phenyllpyrrolor3,2-blpyridi n-1 -

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -morpholinoethanone

(Intermediate 1 1 ) and (4-fiuoro~3-(trifiuoromethyl)phenyi)boronic acid. MS (ESI): mass calcd, for C20H ₁ 7F4N3O2, 407,1 ; m/z found, 408.2 [M+H] ^{+ 1} H NMR (400 MHz, CD3OD) δ 8.58 (d, J = 2.0 Hz, 1 H), 8.13 - 8.10 (m, 1 H), 8.01 - 7.95 (m, 2H), 7.57 (d, J = 3.3 Hz, 1 H), 7.49 - 7.41 (m, 1 H), 6.69 (dd, J = 3.3, 0.8 Hz, 1 H), 5.31 (s, 2H), 3.81 - 3,75 (m, 2H), 3,72 - 3.64 (m, 4H), 3.61 - 3.55 (m, 2H). -(Azetidin-1 -yl)-2-i6-i2-(trifluoromethyl)-4-pyridyl]pyrroloi3,2-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(azetidin-1 ~yi)-2~(6~bromo-1 H-pyrrolo[3,2~b]pyridin~1 -yi)ethanone (Intermediate 14) and (2-(trifluoromethyl)pyridin-4-yi)boronic acid. MS (ESI): mass caicd. for C ₈ H ₅ F ₃ N ₄ 0, 360.1 ; m/z found, 361 .2 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.79 - 8,73 (m, 2H), 8,35 - 8,32 (m, 1 H), 8.21 (d, J = 2.0 Hz, 1 H), 8.03 (dd, J = 5.2, 1 .7 Hz, 1 H), 7.66 (d, J = 3.3 Hz, 1 H), 6.71 (dd, J = 3.3, 0.9 Hz, 1 H), 5.06 (s, 2H), 4.32 (t, J = 7.7 Hz, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.44 - 2.34 (m, 2H), -Cvclopropyl-2-f6-r2-(trifluoromethyl)-4-pyridyllpyrrolof3.2 -

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo- H-pyrrolo[3 _! 2-b]pyridin-1 -yl)-N-cyclopropylacetamide

(intermediate of Step A, Example 75) and (2-(trifluoromethyi)pyridin-4- yi)boronic acid. MS (ESI): mass calcd. for C18H15F3N4O, 360.1 ; m/z found, 361 .2 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) δ 8.80 - 8.74 (m, 2H), 8.33 - 8.30 (m, 1 H), 8.21 - 8, 19 (m, 1 H), 8.03 (dd, J = 5.1 , 1 .7 Hz, 1 H), 7.67 (d, J = 3.3 Hz, 1 H), 6.72 (dd, J = 3.3, 0.9 Hz, 1 H), 4.97 (s, 2H), 2.74 - 2.67 (m, 1 H), 0.77 - 0.70 (m, 2H), 0.56 - 0.50 (m, 2H).

Example ^clopropyl-2-[6-i6-(trif!uoromethyl)-2- b]pyridin-1 -yllacetamide.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N-cyclopropylacetamide

(intermediate of Step A, Example 75) and (5-(trifluoromethyl)pyridin-3- yljboronic acid. MS (ESI): mass calcd. for Ci ₈ Hi5F ₃ N ₄ 0, 360.1 ; m/z found, 361 .2 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 9.06 (d, J = 1 .9 Hz, 1 H), 8.53 -

8.50 (m, 1 H), 8.21 (d, J = 8.1 Hz, 1 H), 8.07 (t, J = 7.9 Hz, 1 H), 7.74™ 7.69 (m, 1 H), 7.64 (d, J = 3.3 Hz, 1 H), 6.68 (dd, J = 3.3, 0.9 Hz, 1 H), 4.93 (s, 2H), 2.74 - 2.67 (m, 1 H), 0.76 - 0.70 (m, 2H), 0.58 - 0,53 (m, 2H). -(Azetidin-1 -yl)-2-f6-(6-methyl-3-pyridyl)pyrrolof3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)ethanone

(Intermediate 14) and (6-methylpyridin-3-yl)boronic acid, MS (ESI): mass calcd. for C ₈ H ₁₈ N ₄ 0, 306.1 ; m/z found, 307.2 [M+H] ⁺ . ¹ H NMR (400 MHz, CD3OD) δ 8.75 (d, J = 2.4 Hz, 1 H), 8.60 (d, J = 1 .8 Hz, 1 H), 8.14 - 8.12 (m, 1 H), 8.08 (dd, J = 8.1 , 2.5 Hz, 1 H), 7.59 (d, J = 3.5 Hz, 1 H), 7.43 (d, J = 8.1 Hz, 1 H), 6.69 (dd, J = 3.3, 0.8 Hz, 1 H), 5.03 (s, 2H), 4.28 (t, J = 7.7 Hz, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.60 (s, 3H), 2.42 - 2.32 (m, 2H).

Example 1 13: 5-f 1 -[2-(Azetidin-1 -yl)-2-oxo-ethyl]pyrrolo[3,2-b]pyridin-6- yi]pyridine-2-carbonitrile.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)ethanone (Intermediate 14) and 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yi)picoiinanitriie. MS (ESI): mass calcd. for C18H15N5O, 317.1 ; m/z found, 318.1 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 9.10 - 9.07 (m, 1 H), 8.69 (d, J = 1 .9 Hz, 1 H), 8.36 - 8.30 (m, 1 H), 8.26 - 8.21 (m, 1 H), 7.99 - 7.93 (m, 1 H), 7.67 - 7.63 (m, 1 H), 6.72 - 6.69 (m, 1 H), 5.04 (s, 2H), 4.31 (t, J = 7.8 Hz, 2H), 4.07 (t, J = 7.9 Hz, 2H), 2.44 - 2.32 (m, 2H). -(3,4-Difluorophenyl)-1-(pyrimidin-5-ylmethyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 115 substituting pyrimidin-5-ylmethyl methanesulfonate for (5-fluoropyrimidin-2- yi)methyi methanesulfonate (Intermediate 3). MS (ES!): mass caicd. for CieH ₁₂ F2N4, 322.1; m/z found, 323.1 [M+H] ^{+ 1} H N MR (500 MHz, CD ₃ OD) δ 9.07 (s, 1H), 8.66 (s, 2H), 8.61 (d, J= 1.9 Hz, 1H), 8.20-8.18 (m, 1H), 7.77 (d, J = 3.3 Hz, 1 H), 7.66 - 7.60 (m, 1 H), 7.50 - 7.46 (m, 1 H), 7.39 - 7.33 (m, 1H), 6.74 (dd, J = 3.3, 0,9 Hz, 1 H), 5,62 (s, 2H).

Example 115: 6-(3,4-Difluorophenyl)-1-r(5-fluoropyrimidin-2-

Step A: 6-(3,4-Difluorophenyi)-1 H-pyrroloi3,2-b]pyridine. The title compound was prepared in a manner analogous to Example 106, Step B, substituting (3,4-difluorophenyl)boronic acid for (4-fluoro-3-(trifluoromethyl)phenyl)boronic acid. MS (ES!): mass calcd. for Ci ₃ H ₈ F _{2 2} , 230.1; m/z found, 231.1 [M+H] ⁺ . Step B: 6-(3,4-Difiuorophenyi)-1-i(5-fluoropyrimidin-2-ynmethynpyrro lo[3,2- bipyhdine. The title compound was prepared in a manner analogous to

Example 106 Step A substituting (5-fluoropyrimidin-2-yl)methyl

methanesulfonate (Intermediate 3) for 2-bromo-1-(3,3-difluoroazetidin-1- yijethanone. MS (ES!): mass caicd. for C13H11F3 4, 340.1; m/z found, 341.2 [M+Hf. Ή NMR (500 MHz, CD ₃ OD) δ 8.66 (d, J = 0.8 Hz, 2H), 8.55 (d, J = 1.9 Hz, 1H), 8.13-8.11 (m, 1H), 7.72 (d, J= 3.3 Hz, 1H), 7.62-7.56 (m, 1H), 7.49 - 7.43 (m, 1 H), 7.39 - 7.31 (m, 1 H), 6.66 (dd, J = 3.3, 0.9 Hz, 1 H), 5.70 (s, 2H). yllmethanone.

To a solution of 6-(3,4-difluorophenyl)-1 H-pyrrolo[3,2-b]pyridine (50 mg, 0.22 mmol) in DMF (1 mL) was added cyciobutanecarboxyhc acid (25 μί_, 0.28 mmol), D!PEA (0.1 1 mL, 0.65 mmo!) and HATU (91 mg, 0.24 mmol). The reaction mixture was stirred at room temperature for 1 hour and water was added. The aqueous phase was extracted 3 times with DCM and the combined organic layers were dried (MgSO- , filtered and evaporated.

Purification by HPLC Method A afforded the title compound (28 mg, 41 %). MS (ESI): mass calcd. for C18H14F2N2O, 312.1 ; m/z found, 313.1 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.93 - 8.90 (m, 1 H), 8.68 (d, J = 2.1 Hz, 1 H), 7.97 (d, J = 3.8 Hz, 1 H), 7.65 - 7.59 (m, 1 H), 7.51 - 7.46 (m, 1 H), 7.43 - 7.36 (m, 1 H), 6.79 (d, J = 3.9 Hz, 1 H), 4.10 - 4.01 (m, 1 H), 2.57 - 2.39 (m, 4H), 2.24 - 2.12 (m, 1 H), 2.04 - 1 .94 (m, 1 H). -(3,3-Difluoroazetidin-1 -yl)-2-f6-[6-(trifluoromethyl)-2-

The title compound was prepared in a manner analogous to Example 106 substituting 2-(4,4,S,5-tetramethyi-1 ,3,2-dioxaborolan-2-yl)-6- (trifluoromethyl)pyridine for (4-fluoro-3-(trifluoromethyl)phenyl)boronic acid. MS (ESI): mass calcd. for C18H13F5N4O, 396.1 ; m/z found, 397.2 [Μ+Η] ^÷ . ¹ H NMR (500 MHz, CD ₃ OD) δ 9.10 (d, J = 1 .9 Hz, 1 H), 8.58 - 8.56 (m, 1 H), 8.23 (d, J = 8,0 Hz, 1 H), 8, 12 - 8,07 (m, 1 H), 7.73 (dd, J = 7.7, 0,8 Hz, 1 H), 7,64 (d, J = 3.3 Hz, 1 H), 6.72 (dd, J = 3.3, 0.9 Hz, 1 H), 5.17 (s, 2H), 4.69 (t, J = 1 1 .9 Hz, 2H), 4.42 (t, J = 12.1 Hz, 2H). Example 1 18: 1 -(Azetidin-1 -yl)-2-f6-(2,3,4-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for C^H^FsNsO, 345.1 ; m/z found, 346.2 [M+H] ⁺ . ¹ H NMR (500 MHz, CD3OD) δ 8.49 - 8.46 (m, 1 H), 8.01 (s, 1 H), 7.62 (dd, J = 3.4, 1 .0 Hz, 1 H), 7.42 - 7.35 (m, 1 H), 7.29 - 7.21 (m, 1 H), 6.71 - 6.68 (m, 1 H), 5.00 (s, 2H), 4.27 (t, J = 7.7 Hz, 2H), 4.06 (t, J = 7.8 Hz, 2H), 2.41 - 2.31 (m, 2H).

Example 1 19: 2-Cyclopropyl-1 -[6-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin-1 - yllethanone.

The title compound was prepared in a manner analogous to Example 1 16. MS (ESI): mass calcd. for C^H^i^O, 312.1 ; m/z found, 313.2 [M+H] ⁺ . ¹ H NMR (400 MHz, CD3OD) δ 8.88 (d, J = 2.5 Hz, 1 H), 8.67 (d, J = 2.0 Hz, 1 H), 8.09 (d, J = 3.9 Hz, 1 H), 7.64 - 7.55 (m, 1 H), 7.50 - 7.43 (m, 1 H), 7.42 - 7.30 (m, 1 H), 6.79 (dd, J = 3.8, 0.7 Hz, 1 H), 2.97 (d, J = 6.8 Hz, 2H), 1 .28 - 1 .17 (m, 1 H), 0.68 - 0.61 (m, 2H), 0.35 - 0.29 (m, 2H). -Pyrroiidin-1 -Yl-2-i6-f2,3.4-trifluoropheny0pyrroloi3.2

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrroio[3,2-b]pyridin-1 -yl)-1 -(pyrroiidin-1 -yl)ethanone (Intermediate 10) and (2,3,4-trifluorophenyl)boronic acid. MS (ESI): mass caicd. for C ₉ Hi ₆ F ₃ N ₃ 0, 359.1 ; m/z found, 360.2 [M+H] ⁺ . Ή NMR (400 MHz, CD ₃ OD) δ 8.47 - 8.43 (m, 1 H), 8.00 (s, 1 H), 7.60 (d, J = 3.3 Hz, 1 H), 7.40 - 7.31 (m, 1 H), 7.26 - 7.18 (m, 1 H), 6.68 (dd, J = 3.3, 1 .0 Hz, 1 H), 5.15 (s, 2H), 3.82 (t, J = 6.9 Hz, 2H), 3.44 (t, J = 7.0 Hz, 2H), 2.09 - 2.00 (m, 2H), 1 .95 - 1 .85 (m, 2H).

Example 121 : 1 -(3.3-difluoroazetidin-1 -yl)-2-f6-(3.5- difluorophenyl)pyrrolof3,2-blpyridin-1 -yl1ethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrroio[3,2-b]pyridin-1 -yl)-1 -(3,3-difluoroazetidin-1 - yl)ethanone (Intermediate 12) and (3,5-difluorophenyl)boronic acid, MS (ESI): mass caicd. for C ₈ H ₃ F ₄ N ₃ 0, 363.1 ; m/z found, 364.2 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) 6 8.60 (d, J = 1 .9 Hz, 1 H), 8.15 - 8.12 (m, 1 H), 7.58 (d, J = 3.4 Hz, 1 H), 7.37 - 7,29 (m, 2H), 6.98 - 6.91 (m, 1 H), 6.68 (dd, J = 3,4, 0.9 Hz, 1 H), 5.10 (s, 2H), 4.66 (t, J = 12.0 Hz, 2H), 4.41 (t, J = 12.2 Hz, 2H). -[6-(3.5-Dif luorophenyl)pyrrolof3,2-blpyridin-1 -yll-1 -pyrrolidin-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrroio[3,2-b]pyridin-1 -yl)-1 -(pyrroiidin-1 -yl)ethanone (Intermediate 10) and (3,5-difluorophenyl)boronic acid. MS (ESI): mass calcd. for C gHiyFaNsO, 341 .1 ; m/z found, 342.2 [M+Hf. Ή N MR (500 MHz, CD ₃ OD) δ 8.58 (d, J = 2.1 Hz, 1 H), 8.12 - 8.10 (m, 1 H), 7.58 (d, J = 3.4 Hz, 1 H), 7.37 - 7.29 (m, 2H), 6.96 - 6.91 (m, 1 H), 6.67 (dd, J = 3.3, 0.9 Hz, 1 H), 5.16 (s, 2H), 3.64 (t, J = 6.8 Hz, 2H), 3.46 (t, J = 7.0 Hz, 2H), 2.10 - 2.02 (m, 2H), 1 .95 - 1 .87 (m, 2H).

Example 123: 1 -Pyrrolidin-1 -yl-2-f6-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yilethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -y!)-1 -(pyrrolidin-1 -yl)ethanone (Intermediate 10) and (3,4,5-trifluorophenyl)boronic acid. MS (ESI): mass calcd. for Ci ₉ H ₁₆ F3N ₃ 0, 359.1 ; m/z found, 360.2 [M+Hf. ¹ H NMR (400 MHz, CD3OD) δ 8.55 (d, J = 1 .9 Hz, 1 H), 8.09 - 8.06 (m, 1 H), 7.57 (d, J = 3.3 Hz, 1 H), 7.53 - 7.44 (m, 2H), 6.65 (dd, J = 3.4, 0.9 Hz, 1 H), 5.14 (s, 2H), 3.64 (t, J = 6.8 Hz, 2H), 3.45 (t, J = 6.9 Hz, 2H), 2.1 1 - 2.02 (m, 2H), 1 .96 - 1 .87 (m, 2H). -(3,3-Difluoroazetidin-1 -yl)-2-f6-f 3.4.5·

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3,3-difluoroazetidin-1 - yl)ethanone (Intermediate 12) and (3,4,5-trifluorophenyl)boronic acid. MS (ESi): mass calcd. for C ₈ H ₁₂ F5N ₃ 0, 381 .1 ; m/z found, 382.1 [M+H] ⁺ . ^! H NMR (400 MHz, CD ₃ OD) δ 8.80 (d, J = 2.0 Hz, 1 H), 8.15 - 8.13 (m, 1 H), 7.60 (d, J = 3.3 Hz, 1 H), 7.58 - 7.49 (m, 2H), 8.69 (dd, J = 3.3, 0.9 Hz, 1 H), 5.13 (s, 2H), 4.68 (t, J = 1 1 .9 Hz, 2H), 4.41 (t, J = 12.2 Hz, 2H).

Example 125: 2-[6-(3,5-Difluorophenyl)pyrrolo[3.2-b pyridin-1 -yl]-1 - morphoiino-ethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo~1 H~pyrrolo[3,2~b]pyridin-1 ~yi)-1 -morpholinoethanone (Intermediate 1 1 ) and (3,5-difluorophenyl)boronic acid. MS (ES!): mass calcd. for Ci9H ₁₇ F2N302, 357.1 ; m/z found, 358.2 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.54 (d, J = 1 .9 Hz, 1 H), 8.06 - 8.02 (m, 1 H), 7,53 (d, J = 3.3 Hz, 1 H), 7.31 - 7.23 (m, 2H), 6.96 - 6.88 (m, 1 H), 6.65 (d, J = 3.2 Hz, 1 H), 5.20 (s, 2H), 3.77 - 3.73 (m, 2H), 3.89 - 3.64 (m, 2H), 3.63 - 3.53 (m, 4H). -Morpholino-2-r6-(2,3,4-trifluorophenyl)pyrrolof3,2-blpyridi n-1 ^■

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrroio[3,2-b]pyridin-1 -yl)-1 -morpholinoethanone (Intermediate 1 1 ) and (2,3 _! 4~trifluorophenyl)boronic acid. MS (ESI): mass caicd. for C ₉ H ₁₆ F3N ₃ 02, 375.1 ; m/z found, 376.2 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) δ 8.47 (t, J = 1 .8 Hz, 1 H), 8.04 - 7.99 (m, 1 H), 7.60 (d, J = 3.4 Hz, 1 H), 7.43 - 7.35 (m, 1 H), 7.30 - 7.20 (m, 1 H), 6.70 (dd, J = 3.3, 0.9 Hz, 1 H), 5.30 (s, 2H), 3.79 - 3.73 (m, 2H), 3,72 - 3.62 (m, 4H), 3.61 - 3.55 (m, 2H).

Example 127: 1 -Morpholino-2-[6-(3,4,5-trifluorophenyl)pyrrolof3,2-blpyridi n-1 - yilethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -morpholinoethanone (Intermediate 1 1 ) and (3,4,5-trifluorophenyl)boronic acid. MS (ESI): mass caicd. for Ci9H ₁₆ F3N ₃ 02, 375.1 ; m/z found, 376.2 [M+H] ⁺ . ¹ H NMR (400 MHz, CD3OD) δ 8.54 (d, J = 2.0 Hz, 1 H), 8.07 - 8.04 (m, 1 H), 7.55 (d, J = 3.3 Hz, 1 H), 7.52 - 7.41 (m, 2H), 6.66 (d, J = 3.3 Hz, 1 H), 5.24 (s, 2H), 3.80 - 3.74 (m, 2H), 3.71 - 3.66 (m, 2H), 3.66 - 3.60 (m, 2H), 3.60 - 3.53 (m, 2H). -[6-(3.4-Difluorophenyl)pyrrolof3,2-blpyridin-1 -yll-1 -(3

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1H-pyrrolo[3,2-b]pyridin-1-yl)-1-(3-fluoroazetidi n-1- yi)ethanone (Intermediate 13) and (3,4-difluorophenyi)boronic acid. MS (ESI): mass calcd, for C18H14F3N3O, 345.1; m/z found, 346.2 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.57 (d, J = 1.9 Hz, 1 H), 8.08 - 8.06 (m, 1 H), 7.67 - 7.60 (m, 1 H), 7.57 (d, J = 3.3 Hz, 1 H), 7.52 - 7.48 (m, 1 H), 7.40 - 7.33 (m, 1 H), 6.67 (dd, J= 3.4, 0,9 Hz, 1H), 5.47-5.30 (m, 1H), 5.05 (d, J = 3.4 Hz, 2H), 4.58- 4.48 (m, 1H), 4.40-4.27 (m, 2H), 4.16-4.03 (m, 1H). -i6-(3,5-Difluorophenyl)pyrroloi3,2-b]pyridin-1 -yll-1 -(3-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3 _! 2-b]pyridin-1 -yl)-1 -(3-fluoroazetidin-1 - yl)ethanone (Intermediate 13) and (3,5-difluorophenyl)boronic acid. MS (ESI): mass calcd. for Ci3H ₁₄ F ₃ N ₃ 0, 345.1; m/z found, 346.2 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.61 (d, J = 2.0 Hz, 1H), 8.13 (dd, J = 1.9, 0.9 Hz, 1H), 7.60 (d, J = 3.3 Hz, 1 H), 7.39 - 7.32 (m, 2H), 7.00 - 6.92 (m, 1 H), 6.69 (dd, J = 3.3, 0.9 Hz, 1 H), 5.48 - 5.31 (m, 1 H), 5.07 (d, J = 3.2 Hz, 2H), 4.60 - 4.50 (m, 1 H), 4.40-4.30 (m, 2H), 4.15-4.05 (m, 1H). Example 130: 6-(4-Methyl-2-thienyl)-1 -(pyridazin-3-ylmethyl)pyrrolof3,2-

Step A: 6-(4-Methylfhiophen-2-yl)-1 H-pyrrolof3,2-b]pyridine. The title compound was prepared in a manner analogous to Example 1 15, Step A substituting 4,4,5,5-tetramethyl-2-(4-methylthiophen-2-yl)-1 ,3,2-dioxaborolane for (3,4-difluorophenyl)boronic acid. MS (ES!): mass calcd. for C 2H10N2S, 214.1 ; m/z found, 215.1 [M+H] ⁺ .

Step B: 6-(4-Methyl-2-thienyl)-1 -(pyridazin-3-ylmethyl)pyrrolof3,2-blpyridine. The title compound was prepared in a manner analogous to Example 1 15, Step B, using 6-(4~methyithiophen-2~yi)-1 H-pyrrolo[3,2-b]pyridine and 3- (chioromethyl)pyridazine hydrochloride. MS (ESI): mass calcd. for C17H14N4S, 306.1 ; m/z found, 307.1 [M+Hf. ¹ H NMR (500 MHz, CD ₃ OD) δ 9.10 (dd, J = 5.0, 1 .6 Hz, 1 H), 8.58 (d, J = 1 .9 Hz, 1 H), 8.08 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.74 (d, J = 3.3 Hz, 1 H), 7.65 (dd, J = 8.6, 4.9 Hz, 1 H), 7.45 (dd, J = 8.5, 1 .6 Hz, 1 H), 7.25 (d, J = 1 .4 Hz, 1 H), 6.96 (s, 1 H), 6.69 (dd, J = 3.4, 1 .0 Hz, 1 H), 5.80 (s, 2H), 2.27 (s, 3H).

The title compound was prepared in a manner analogous to Example 1 15 substituting 3-(chloromethyl)pyridazine hydrochloride for (5-fluoropyrimidin-2- yi)methy! methanesulfonate (Intermediate 2). MS (ESI): mass calcd. for C 8H12F2N4, 322.1 ; m/z found, 323.1 [M+H] ⁺ . ¹ H N MR (500 MHz, CD ₃ OD) δ 9.10 (dd, J = 4.9, 1 .6 Hz, 1 H), 8.58 (d, J = 2.0 Hz, 1 H), 8.17 (dd, J = 2.0, 0.9 Hz, 1 H), 7.79 (d, J = 3.3 Hz, 1 H), 7.65 (dd, J = 8.5, 5.0 Hz, 1 H), 7.63 - 7.57 (m, 1 H), 7.51 - 7.43 (m, 2H), 7.38 - 7.31 (m, 1 H), 6.72 (dd, J = 3.3, 0.9 Hz, 1 H), 5.83 (s, 2H). Example 132: 2-f6-f4-Methyl-2-thienyl)pyrrolof3,2-blpyridin-1 -yll-1 - morphoiina-ethanone.

The title compound was prepared in a manner analogous to Example 85 substituting 4,4,5,5-tetramethyl-2~(4-methylthiophen~2-yl)~1 ,3,2-dioxaborolane for phenylboronic acid. MS (ESI): mass calcd. for C18H19 3O2S, 341 .1 ; m/z found, 342.2 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 8.00 - 7.97 (m, 1 H), 7.49 (d, J = 3.3 Hz, 1 H), 7.26 (d, J = 1 .4 Hz, 1 H), 6.98 - 6.96 (m, 1 H), 6.62 (dd, J = 3.3, 0.9 Hz, 1 H), 5.22 (s, 2H), 3.78 - 3.73 (m, 2H), 3.70 - 3.66 (m, 2H), 3.65 - 3.61 (m, 2H), 3.59 - 3.55 (m, 2H), 2.29 (d, J = 1 .1 Hz, 3H).

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)ethanone (Intermediate 14) and (2,4-difluorophenyl)boronic acid. MS (ESI): mass calcd. for 327.1 ; m/z found, 328.2 [M+H] ^{+ 1} H NMR (500 MHz, CD3OD) δ 8.46 (s, 1 H), 7.98 (s, 1 H), 7.63 - 7.55 (m, 2H), 7.14 - 7.07 (m, 2H), 6.68 (d, J = 3.2 Hz, 1 H), 4.98 (s, 2H), 4,24 (t, J = 7.7 Hz, 2H), 4.05 (t, J = 7.8 Hz, 2H), 2.39 - 2.30 (m, 2H).

Example 134: 1 -(Azetidin-1 -yl)-2-r6-(2,3-difluorophenyl)pyrrolof3 ₁ 2-blpyridin- -yilethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -y!)ethanone (Intermediate 14) and (2,3-difluorophenyl)boronic acid. MS (ESI): mass calcd. for Ci ₈ Hi5F ₂ N ₃ 0, 327.1 ; m/z found, 328.2 [M+H] ⁺ . ¹ H HMR (500 MHz,

CD ₃ OD) δ 8.52 - 8.49 (m, 1 H), 8.04 (s, 1 H), 7.61 (d, J = 3.3 Hz, 1 H), 7.40 - 7.35 (m, 1 H), 7.34 - 7.25 (m, 2H), 6.70 (dd, J = 3.4, 1 .0 Hz, 1 H), 5.00 (s, 2H), 4.26 (t, J = 7.7 Hz, 2H), 4.06 (t, J = 7.8 Hz, 2H), 2.40 - 2.31 (m, 2H). Example 135: 1 -(Azetidin-1 -yl)-2-f6-(2,5-difluorophenyl)pyrrolof3,2-blpyridin- -yi]ethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(azetidin-1 -yl)-2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)ethanone (Intermediate 14) and (2,5-difluorophenyi)boronic acid. MS (ESI): mass calcd. for C 8Hi5F ₂ N ₃ 0, 327.1 ; m/z found, 328.2 [M+H] ⁺ . Ή NMR (500 MHz, CD3OD) δ 8.53 - 8.51 (m, 1 H), 8.03 (s, 1 H), 7.61 (d, J = 3.3 Hz, 1 H), 7.41 - 7.34 (m, 1 H), 7.30 - 7.23 (m, 1 H), 7.18 - 7.12 (m, 1 H), 6.69 (d, J = 3.3 Hz, 1 H), 5.00 (s, 2H), 4.26 (t, J = 7.7 Hz, 2H), 4.06 (t, J = 7.8 Hz, 2H), 2.40 - 2.32 (m, 2H). Example 136: 1 -Cvclopropyl-2-f6-(3,4-difluorophenyl)-3-fluoro-pyrrolof3,2-

Step A: 2-(6-Bromo-3-fluoro-1 H-pyrrolor3,2-blpyridin-1 -yl)-1 - cyclopropylethanone. The title compound was prepared in a manner analogous to Intermediate 15, using 2-bromo-1 -cyclopropylethanone and 6- bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridine (Intermediate 6). MS (ESI): mass calcd. for C ₂ H ₁₀ BrFN ₂ G, 296.0; m/z found, 297.0 [M+H] ⁺ .

Step B: 1 -Cyclopropyl^-ie-iS^-difluorophenyn-S-fluoro-pyrroloiS^-blpy ridin- 1 -yl]ethanone. The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 - cyclopropylethanone and (3,4-difluorophenyl)boronic acid. MS (ESI): mass calcd. fGr C ₈ H ₁₃ F ₃ N ₂ 0, 330.1 ; m/z found, 331 .0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-de) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.28 - 8.24 (m, 1 H), 7.88 (ddd, J = 12,3, 7.7, 2.2 Hz, 1 H), 7.69 (d, J = 2,2 Hz, 1 H), 7.67 - 7.52 (m, 2H), 5.42 (s, 2H), 2.16 - 2.07 (m, 1 H), 1 .05 - 0.91 (m, 4H).

Example 137: 6-(4-Methyl-2-thienyl)-1 -[[5-(trifluoromethyl)-2- furyl1methyllpyrrolo[3,2-blpyridine.

The title compound was prepared in a manner analogous to Example 130. MS

(ES!): mass calcd. for C ₈ H ₁₃ F ₃ N ₂ 0S, 362.1 ; m/z found, 363.0 [M+H] ⁺ . Ή

NMR (400 MHz, CD ₃ OD) δ 8.60 (s, 1 H), 8.15 (s, 1 H), 7.65 (d, J = 3.3 Hz, 1 H),

7.29 (s, 1 H), 7.00 (s, 1 H), 6.93 - 6.90 (m, 1 H), 6.65 (d, J = 3.4 Hz, 1 H), 6.52 (d, J = 3.4 Hz, 1 H), 5.55 (s, 2H), 2.30 (s, 3H). furyl1methyllpyrrolo[3,2-blpyridine.

The title compound was prepared in a manner analogous to Example 1 15 substituting 2-(bromomethy!)-5-(trif!uoromethy!)furan for (5-fluoropyrimidin-2- yl)methyl methanesuifonate (Intermediate 2). MS (ESI): mass caicd. for C19H11 F5N2O, 378.1 ; m/z found, 379.0 [fVH-H] ^{÷ 1} H NMR (400 MHz, CD ₃ OD) δ 8.58 (d, J = 1 .9 Hz, 1 H), 8.23 - 8.20 (m, 1 H), 7.69 (d, J = 3.4 Hz, 1 H), 7.66 - 7.59 (m, 1 H), 7.52 - 7.46 (m, 1 H), 7.41 - 7.33 (m, 1 H), 6.92 - 6,89 (m, 1 H), 6.68 (d, J = 3.3 Hz, 1 H), 6.53 (d, J = 3.4 Hz, 1 H), 5.57 (s, 2H).

Example 139: N,N-Dimethyl-2-f6-(4-methyl-2-thienyl)pyrrolof3,2-blpyridin- 1 - yllacetamide.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2~(6~bromo-1 H-pyrroio[3,2-b]pyridin~1 -yl)~N,ISI~dimethylacetamide (Example 375, Intermediate from Step A) and 4,4,5,5-tetramethyl-2-(4- methylthiophen-2-yl)-1 ,3,2-dioxaborolane. MS (ESI): mass calcd. for

C 6H17N3OS, 299.1 ; m/z found, 300.1 [M+H] ⁺ . Ή NMR (500 MHz, CD ₃ OD) δ 8.55 (d, J = 1 .9 Hz, 1 H), 7.97 - 7,94 (m, 1 H), 7.47 (d, J = 3.3 Hz, 1 H), 7.25 (d, J = 1 .4 Hz, 1 H), 6.96 (s, 1 H), 6.61 (dd, J = 3.3, 0.9 Hz, 1 H), 5.19 (s, 2H), 3.17 (s, 3H), 2.97 (s, 3H), 2.28 (s, 3H). -[6-(3.4-Difluorophenyl)pyrrolof3,2-blpyridin-1 -νΠ-3.3·

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SStteepp BB:: 11 --[[66--((33,,44--DDiifflluuoorroopphheennyyll))ppyyrrrrooll oorr33,,22--bbllppyyrriiddiinn--11 --yyli]]--33,,33--ddiimmeetthhyyll--bbuuttaann-- 1100 22 --oonnee.. TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 11 ,, SStteepp AA,, uussiinngg 11 --((66--bbrroommoo--11 HH--ppyyrrrroolloo[[33,,22--bb]]ppyyrriiddiinn--11 --yyll))--33,,33--ddiimmeetthhyyllbbuuttaann--

22--oonnee aanndd ((33,,44--ddiiffiiuuoorroopphheennyyll))bboorroonniicc aacciidd.. MMSS ((EESSII)):: mmaassss ccaallccdd.. ffoorr

CC ₉₉ HHii ₈₈ FF ₂₂ NN ₂₂ 00,, 332288..11 ;; mm//zz ffoouunndd,, 332299..11 [[MM++HH]] ⁺⁺ .. ΉΉ NNMMRR ( (550000 MMHHzz,, CCDD ₃₃ OODD)) δδ 88..5544 ((ss,, 11 HH)),, 77..8899 ((ss,, 11 HH)),, 77..8633 -- 77..5566 ((mm,, 11 HH)),, 77..5500 -- 77..4433 ((mm,, 22HH)),, 77..3399 -- 1155 77..3322 ((mm,, 11 HH)),, 66..6666 ((dd,, JJ == 33..33 HHzz,, 11 HH)),, 55..4444 ((ss,, 22HH)),, 11 ..3322 ((ss,, 99HH))..

EExxaammppllee 114411 :: 11 --ff66--((44--FFlluuoorroo--33--mmeetthhyyll--pphheennyyll)) ppyyrrrroolloo[[33,,22--bbllppyyrriiddiinn--11 --yyllll--33,,33--

The title compound was prepared in a manner analogous to Example 140. MS (ESI): mass calcd. for C ₂₀ H ₂ FN ₂ G, 324.2; m/z found, 325.1 [M+H] ⁺ . Ή NMR (500 MHz, CD ₃ OD) δ 8.51 (d, J = 1 .9 Hz, 1 H), 7.82 (s, 1 H), 7.52 - 7,49 (m, 1 H), 7.47 - 7.42 (m, 2H), 7.14 - 7.09 (m, 1 H), 6.64 (dd, J = 3.3, 0.9 Hz, 1 H), 5.41 (s, 2H), 2.34 (d, J = 1 .9 Hz, 3H), 1 .31 (s, 9H).

25 -[6-(3.5-Difluorophenyl)pyrrolof3,2-blpyridin-1 -yll-3.3-

The title compound was prepared in a manner analogous to Example 140. S (ESI): mass calcd. for C19H18F2N2O, 328.1 ; m/z found, 329.1 [M+H] ⁺ . ¹ H NMR (500 MHz, CD3OD) δ 8.58 (d, J = 1 .9 Hz, 1 H), 7.96 - 7.94 (m, 1 H), 7.50 (d, J = 3.3 Hz, 1 H), 7.34 - 7.28 (m, 2H), 6.98 - 6.91 (m, 1 H), 6.67 (dd, J = 3.4, 0.9 Hz, 1 H), 5.45 (s, 2H), 1 .32 (s, 9H). -Dimethyl-1 -r6-(4-methyl-2-thienyl)pyrrolof3,2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 140 substituting 4,4,5,5-tetramethyl-2-(4-methylthiophen-2-yl)-1 ,3,2-dioxaboroiane for (3,4-difluorophenyl)boronic acid. MS (ESI): mass calcd. for C18H20N2OS, 312.1 ; m/z found, 313.1 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 7.82 - 7.79 (m, 1 H), 7.43 (d, J = 3.3 Hz, 1 H), 7.24 (d, J = 1 .4 Hz, 1 H), 6.98 - 6.95 (m, 1 H), 6.61 (dd, J = 3.3, 0.9 Hz, 1 H), 5.39 (s, 2H), 2.28 (d, J = 1 .1 Hz, 3H), 1 .32 (s, 9H).

Example 144: 1 -i6-i3-(Difluoromethyl)phenvnpyrrolo[3,2-b]pyridin-1 -yll-3.3- dimethyl-butan-2-one.

The title compound was prepared in a manner analogous to Example 140, MS (ES!): mass calcd. for C20H20F2N2O, 342.2; m/z found, 343.1 [M+H] ⁺ . ¹ H NMR (500 MHz, CD3OD) δ 8.58 (s, 1 H), 7.92 (s, 1 H), 7.83 - 7.77 (m, 2H), 7.62 - 7.53 (m, 2H), 7.48 (d, J = 3,3 Hz, 1 H), 6,84 (t, J = 56,2 Hz, 1 H), 6,66 (dd, J = 3.3, 0.9 Hz, 1 H), 5.43 (s, 2H), 1 .31 (s, 9H).

Example 145: 1 -i6-(3-Ethviphenyl)pyrroto[3,2-b1pyridin-1 -yl1-3,3-dimethyl- butan-2-one.

The title compound was prepared in a manner analogous to Example 140. MS (ESI): mass calcd. for C21 H24N2O, 320.2; m/z found, 321 .1 [M+H] ⁺ H NMR (500 MHz, CD3OD) δ 8.54 (d, J = 1 .9 Hz, 1 H), 7.84 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.49 - 7.41 (m, 3H), 7.37 (t, J = 7.6 Hz, 1 H), 7.21 (d, J = 7.6 Hz, 1 H), 6.64 (dd, J = 3.3, 0.9 Hz, 1 H), 5.42 (s, 2H), 2.72 (q, J = 7.6 Hz, 2H), 1 .31 (s, 9H), 1 .28 (t, J = 7.6 Hz, 3H).

Example 146: 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 -

Step A: 2-f6-Bromo-3-chloro-1 H-pyrrolof3,2-blpyridin-1 -yl)-N.N- dimethylacetamide. To a solution of 6-bromo~3-chloro~1 H~pyrroio[3,2- bjpyridine (Intermediate 5, 500 mg, 2.16 mmol) in DMF (60 mL) at 0 °C was added NaH (121 mg, 3.02 mmol, 60% dispersion in oil). The reaction mixture was stirred for 30 minutes at rt, then cooled to 0 °C and 2-bromo-N,N- dimethylacetamide (430 mg, 2.59 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. The reaction mixture was concentrated onto silica gel. Purification (FCC, SiOa, 0- 30% MeOH in DCM) gave the title compound (282 mg, 41 %). MS (ES!): mass caicd, for Cii Hn BrCIN ₃ 0, 315.0; m/z found, 316.0 [M÷ }

Step B: 2-f3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridi n-1 -yil- N. N-dimethyi-acetamide. To a solution 2-(6-bromo-3-chloro-1 H-pyrrolo[3,2- b]pyridin-1 -yl)-N, N-dimethylacetamide (100 mg, 0.31 mmoi) in dioxane (2.9 mL) was added (4-fluoro-3-methyiphenyi)boronic acid (73 mg, 0.47 mmoi), Pd(dppf)CI ₂ (16 mg, 0.02 mmoi), Cs ₂ C0 ₃ (205 mg, 0.63 mmoi) and water (0.6 mL). After 3 hours at 90 °C the reaction mixture cooled and NaHCOs (aq) was added. The reaction mixture was extracted with EtOAc (3 x 60 mL). The combined organics were dried ( gS04), filtered, and concentrated under reduced pressure. Purification (basic HPLC 5-95% ACN) afforded the title compound (36 mg, 33%). MS (ES!): mass caicd. for C13H17CIFIM3O, 345.1 ; m/z found, 346.1 [M+H] ⁺ H NMR (500 MHz, CDCI ₃ ) δ 8.69 (d, J = 1 .9 Hz, 1 H), 7.62 (d, J = 1 .9 Hz, 1 H), 7,41 - 7,33 (m, 2H), 7.31 (s, 1 H), 7.09 (t, J = 8.9 Hz, 1 H), 4.90 (s, 2H), 3.12 (s, 3H), 3.00 (s, 3H), 2.35 (d, J = 2.0 Hz, 3H).

Example 147: 2-[3-Chloro-6-(3,4-difluorophenyl)pyrrolof3,2-blpyridin-1 -yil- N. N-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass caicd. for C17H1 ₄ C 2N3O, 349.1 ; m/z found, 350,0 [M+Hf. H NMR (500 MHz, CDCI3) δ 8.71 (d, J = 1 .9 Hz, 1 H), 7.64 (d, J = 1 .8 Hz, 1 H), 7.43 - 7.38 (m, 1 H), 7.36 (s, 1 H), 7.35 - 7.30 (m, 1 H), 7.29 - 7.23 (m, 1 H), 4.93 (s, 2H), 3.15 (s, 3H), 3.02 (s, 3H). -[3-Chloro-6-(3.5-difluorophenyl)pyrrolof3,2-blpyridin-1 -vi]

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C17H14CIF2N3O, 349.1; m/z found, 350.0 [M+Hf. H NMR (500 MHz, CDCI3) δ 8.73 (d, J = 1.9 Hz, 1 H), 7.67 (d, J = 1.9 Hz, 1 H), 7.38 (s, 1H), 7.17-7.11 (m, 2H), 6.86-6.79 (m, 1H), 4.94 (s, 2H), 3.15 (s, 3H), 3.03 (s, 3H). Example 149: 2-i3-Chloro-6-(4-methyl-2-thienvnpyrrolo[3.2-b]pyridin-1 -yll- N,N~dimetbyi-acetamide.

The title compound was prepared in a manner analogous to Example 146 substituting4 ,4,5,5-tetramethyl-2-(4-methylthiophen-2-yl)-1,3,2-dioxaboro lane for (4-fluoro-3-methylphenyl)boronic acid. !VIS (ESI): mass calcd. for

Ci ₆ H ₁₆ CiN ₃ OS, 333.1; m/z found, 334.0 [M+H] ⁺ . ^! H NMR (500 MHz, CDCi ₃ ) δ 8.78 (d, J = 1.8 Hz, 1H), 7.63 (d, J = 1.8 Hz, 1H), 7.30 (s, 1H), 7.15 (d, J = 1.4 Hz, 1H), 6.90 (s, 1H), 4.88 (s, 2H), 3.12 (s, 3H), 3.01 (s, 3H), 2.30 (d, J= 1.1 Hz, 3H).

-[3-Chloro-6-f3-(difluoromethvnphenyllpyrrolof3,2-blpyrid in-

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci8H ₆ CIF2N ₃ O _l 363.1 ; m/z found, 364.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CDCI ₃ ) δ 8.76 (d, J = 1 .9 Hz, 1 H), 7.76 - 7.67 (m, 3H), 7.60 - 7.49 (m, 2H), 7.35 (s, 1 H), 6.73 (t, J = 56.4 Hz, 1 H), 4.93 (s, 2H), 3.14 (s, 3H), 3.01 (s, 3H). -r3-Chloro-6-(3-ethylphenyl)pyrrolof3,2-blpyridin-1 -vn-N.N

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for CI 9H ₂ QC!N ₃ 0, 341 .1 ; m/z found, 342.1 [M+H] ^{+ 1} H NMR (500 MHz, CD ₃ OD) 5 8.63 (s, 1 H), 8.10 (s, 1 H), 7.61 - 7.47 (m, 3H), 7.40 (t, J = 7.3 Hz, 1 H), 7.25 (d, J = 7.6 Hz, 1 H), 5.29 (s, 2H), 3.20 (s, 3H), 2.98 (s, 3H), 2.74 (q, J = 7.5 Hz, 2H), 1 .30 (t, J = 7.6 Hz, 3H).

The title compound was prepared in a manner analogous to Example 146, MS (ES!): mass calcd. for C17H13C 3N3O, 367.1 ; m/z found, 368.0 [M+H] ⁺ . H NMR (500 MHz, CDCI ₃ ) δ 8.68 (d, J = 1 .9 Hz, 1 H), 7.63 (d, J = 1 .9 Hz, 1 H), 7.38 (s, 1 H), 7.25 - 7.20 (m, 2H), 4,94 (s, 2H), 3, 16 (s, 3H), 3.03 (s, 3H).

Example 153: N-Cvclopropyl-2-i6-(4-methyl-2-thienyl)pyrrolo[3,2-blpyridin -1 - yllacetamide trifiuoroacetate salt.

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C17H17N3OS, 31 1 .1 ; m/z found, 312.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 8,88 (s, 1 H), 8,60 (s, 1 H), 8,41 (d, J = 4.3 Hz, 1 H), 8.00 (s, 1 H), 7.55 (s, 1 H), 7.27 (s, 1 H), 6.79 - 6.75 (m, 1 H), 5.04 (s, 2H), 2.69 - 2.62 (m, 1 H), 2.29 (t, J = 1 .3 Hz, 3H), 0.68 - 0.62 (m, 2H), 0.49 - 0.44 (m, 2H).

Example 154: N-Cvclopropyl-2-f6-(2,3-dimethylphenyl)pyrrolof3.2-blpyridin -1 - yllacetamide trifiuoroacetate salt.

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C20H21 N ₃ 0, 319.2; m/z found, 320.2 [M+H] ⁺ H NMR (500 MHz, DMSO-cfe) δ 8,67 (d, J = 1 ,5 Hz, 1 H), 8,56 (s, 1 H), 8.38 (d, J = 4.1 Hz, 1 H), 8.14 (d, J = 3.2 Hz, 1 H), 7.33 - 7.29 (m, 1 H), 7.25 (t, J = 7.5 Hz, 1 H), 7.21 - 7.18 (m, 1 H), 6.86 (dd, J = 3.3, 0.9 Hz, 1 H), 5.06 (s, 2H), 2.66 - 2.59 (m, 1 H), 2.35 (s, 3H), 2.16 (s, 3H), 0.66 - 0.60 (m, 2H), 0.45 - 0.40 (m, 2H). -Cvclopropyl-2-i8-(m-tolyl)pyrroloi3,2-b]pyridin-1

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for Ci ₉ H ₁₉ N ₃ 0, 305.2; m/z found, 306.2 [M÷ } H NMR (500 MHz, DMSO-cfe) δ 9.00 (s, 1 H), 8.92 (s, 1 H), 8.43 (d, J = 4.1 Hz, 1 H), 8.16 - 8.12 (m, 1 H), 7.69 (s, 1 H), 7.66 (d, J = 7.9 Hz, 1 H), 7.49 - 7.44 (m, 1 H), 7.31 (d, J = 7.5 Hz, 1 H), 6.87 - 6.83 (m, 1 H), 5.13 (s, 2H), 2.69 - 2.62 (m, 1 H), 2.43 (d, J = 1 .7 Hz, 3H), 0.68 - 0.61 (m, 2H), 0.49 - 0.43 (m, 2H).

EExxaammppllee 115566:: NN--CCvycclloopprrooppyyll^-2--ffe6--O(3^,4--ddiicchhlloorro opphheennyynnppyyrrrroollooffS3^,2--bbllppyyrriiddiinn--l1 --

The title compound was prepared in a manner analogous to Example /5. MS (ESI): mass calcd. for CisHisC NsO, 359.1 ; m/z found, 360.1 [M4-H] ^÷ H NMR (500 MHz, DMSO-cfe) δ 8.99 (d, J = 1 .8 Hz, 1 H), 8.80 (s, 1 H), 8.40 (d, J = 4.1 Hz, 1 H), 8.17 (d, J = 2.1 Hz, 1 H), 8.05 (d, J ^ 3.3 Hz, 1 H), 7.89 - 7.82 (m, 2H), 6.81 (dd, J = 3.3, 0.9 Hz, 1 H), 5.06 (s, 2H), 2.69 - 2.62 (m, 1 H), 0.67 - 0.62 (m, 2H), 0.48 - 0.44 (m, 2H).

-Cvclopropyl-2-i6-i2-niethvi-3-

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C20H18F3N3O, 373.1 ; m/z found, 374.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.67 - 8.64 (m, 1 H), 8.50 (s, 1 H), 8.37 - 8.33 (ni, 1 H),

8.08 - 8.04 (m, 1 H), 7,85 - 7,81 (m, 1 H), 7.66 (d, J = 7.7 Hz, 1 H), 7.56 (t, J =

7.9 Hz, 1 H), 6.84 - 6.81 (m, 1 H), 5.01 (s, 2H), 2.66 - 2.59 (m, 1 H), 2.34 (s, 3H), 0.65 - 0.59 (m, 2H), 0.45 - 0.39 (m, 2H).

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for Ci ₈ H ₁₇ N ₃ 0, 291 .1 ; m/z found, 292.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 9.03 (d, J = 1 .6 Hz, 1 H), 8.97 (s, 1 H), 8.42 (d, J = 4.1 Hz, 1 H), 8.16 (d, J = 3.3 Hz, H), 7.90 - 7.85 (m, 2H), 7.62 - 7.57 (m, 2H), 7.53 - 7.48 (m, 1 H), 6.87 (dd, J = 3.3, 0.8 Hz, 1 H), 5.13 (s, 2H), 2.68 - 2.62 (m, 1 H), 0.67 - 0.61 (m, 2H), 0.48 - 0.43 (m, 2H). -Cvclopropyl-2-f6-(4-fluoro-2,3-dimethyl-phenyl)pyrrolor3.2-

The title compound was prepared in a manner analogous to Example 75. MS (ES!): mass calcd. for 0 ₂ οΗ ₂ οΡΝ ₃ 0, 337.2; m/z found, 338.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-ds) δ 8.63 (d, J = 1 .5 Hz, 1 H), 8.50 (s, 1 H), 8.37 (d, J = 4.1 Hz, 1 H), 8.1 1 (d, J = 3.3 Hz, 1 H), 7.27 - 7.15 (m, 2H), 6.84 (d, J = 3.3 Hz, 1 H), 5.04 (s, 2H), 2.65 - 2.59 (m, 1 H), 2.25 (d, J = 2.1 Hz, 3H), 2.19 (s, 3H), 0.66 - 0.60 (m, 2H), 0.45 - 0.40 (m, 2H).

Example 160: N-Cvclopropyl-2-f6-(o-tolyl)pyrrolo[3,2-b]pyridin-1 - yilacetamide.

The title compound was prepared in a manner analogous to Example 75. MS (ES!): mass calcd. for 0 ₉ Η ₁₉ Ν ₃ 0, 305.2; m/z found, 306.2 [M+H] ⁺ . H NMR (500 MHz, DMSO-d ₆ ) δ 8.35 - 8.27 (m, 2H), 7.78 (s, 1 H), 7.67 - 7.58 (m, 1 H), 7.39 - 7.24 (m, 4H), 6,60 (d, J = 3.4 Hz, 1 H), 4.82 (s, 2H), 2.66 - 2.60 (m, 1 H), 2.27 (s, 3H), 0.66 - 0.58 (m, 2H), 0.45 - 0.37 (m, 2H). Example 161 : N-Cyclopropyl-2-r6-(4-fluoro-2-methyl-phenyl)pyrrolor3,2- b]pyridin-1 -yilacetamide trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 75. MS (ES!): mass calcd. for Ci ₉ Hi ₈ FN ₃ 0, 323.1 ; m/z found, 324.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ds) δ 8.72 (s, 1 H), 8.64 (s, 1 H), 8.38 (d, J = 4.4 Hz, 1 H), 8.16 (d, J = 3.2 Hz, 1 H), 7.42 (dd, J = 8.4, 5.9 Hz, 1 H), 7.30 (dd, J = 10.2, 3,0 5 Hz, 1 H), 7.27 - 7.18 (m, 1 H), 6.87 (d, 3.3 Hz, 1 H), 5.07 (s, 2H), 2.67 - 2.61 (m, 1 H), 2.30 (d, J = 2.2 Hz, 3H), 0.69 - 0.60 (m, 2H), 0.47 - 0.39 (m, 2H).

Example 162: 1 -(Azetidin-1 -yl)-2-r6-(o-tolyl)pyrrolo[3,2-blpyridin-1 -

10 yllethanone trifluoroacetate salt.

TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 7711 uussiinngg 11 --((aazzeettiiddiinn--11 --yyll))--22--((66--bbrroommoo--11 HH--ppyyrrrroolloo[[33,,22--bbj]ppyyrriiddiinn--11 --yyll))eetthhaannoonnee aanndd oo--ttooiiyyllbboorroonniicc aacciidd.. MMSS ((EESSII)):: mmaassss ccaallccdd.. ffoorr GC1199HH1199NN33OO,, 330055..22;; mm//zz ffoouunndd,, 1155 330066..22 [[MM++HH]] ⁺⁺ .. HH NNMMRR ((550000 MMHHzz,, DDMMSSOO--dd ₆₆ )) δδ 88..7722 ((ss,, 11 HH)),, 88..6666 ((ss,, 11 HH)),, 88..11 11 -- 88..0077 ((mm,, 11 HH)),, 77..4433 -- 77..3344 ((mm,, 44HH)),, 66..8888 -- 66,,8844 ((mm,, 11 HH)),, 55..1188 ((ss,, 22HH)),, 44,,3300 -- 44..2222 ((mm,, 22HH)),, 33..9944 -- 33..8866 ((mm,, 22HH)),, 22..3322 -- 22..2244 ((mm,, 55HH))..

EExxaammppllee 116633:: 11 --((AAzzeettiiddiinn--11 --yyll))--22--[[66--((44--fflluuoorroo--22--mmeetthhyyll--pp hheennyyll))ppyyrrrroollooff33,,22--

The title compound was prepared in a manner analogous to Example 71 . MS (ESI): mass calcd. for C ₉ Hi ₈ FIM ₃ 0, 323.1 ; m/z found, 324.2 [M+H] ⁺ . ¹ H NMR

(400 MHz, DMSO-cfe) δ 8,67 (d, J = 1 .6 Hz, 1 H), 8.59 (s, 1 H), 8.06 (d, J = 3.2 Hz, 1 H), 7.41 (dd, J = 8.5, 6.0 Hz, 1 H), 7.29 (dd, J = 10.1 , 2.8 Hz, 1 H), 7,21 (id, J = 8.5, 2.9 Hz, 1 H), 6.85 (dd, J = 3.3, 0.7 Hz, 1 H), 5.16 (s, 2H), 4.26 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.34 - 2.24 (m, 5H).

Example 164: 1 -(Azetidin- -yl)-2-f6-(4-fluoro-2,3-dimethyl-phenyl)pyrrolo[3 ₁ 2-

The title compound was prepared in a manner analogous to Example 71 . MS (ESI): mass calcd. for C ₂ oH ₂ oFN ₃ 0, 337.2; m/z found, 338.2 [M+H] ⁺ . Ή NMR (400 MHz, DMSO-ds) δ 8.57 (s, 1 H), 8.42 (s, 1 H), 7.99 (d, J = 3.4 Hz, 1 H), 7.25 - 7.13 (m, 2H), 6.81 (d, 3.3 Hz, 1 H), 5.12 (s, 2H), 4.24 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.31 - 2.22 (m, 5H), 2.17 (s, 3H).

Example 165: 1 -(Azetidin-1 -yl)-2-i6-(2,3-dimethylphenyl)pyrroloi3.2-blpyridin- 1 -yllethanone trifiuoroacetate salt.

The title compound was prepared in a manner analogous to Example 71 . MS (ESI): mass calcd. for C ₂₀ H ₂ i N ₃ 0, 319.2; m/z found, 320.2 [M+H] ⁺ . H NMR (400 MHz, DMSO-d ₆ ) δ 8.66 (d, J = 1 .6 Hz, 1 H), 8.59 (s, 1 H), 8.07 (d, J = 3.3 Hz, 1 H), 7.31 (dd, J = 7.6, 1 .5 Hz, 1 H), 7.25 (t, J = 7.5 Hz, 1 H), 7.19 (dd, J = 7.7, 1 .6 Hz, 1 H), 6.86 (d, J = 3, 1 Hz, 1 H), 5.17 (s, 2H), 4.26 (t, J = 7.6 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.35 (s, 3H), 2.33 - 2.24 (m, 2H), 2.15 (s, 3H). -(Azetidin-1 -yl)-2-f6-r3-(trifluoromethyl)phenyllpyrrolor3,2-

The title compound was prepared in a manner analogous to Example 71 . MS (ESi): mass calcd. for C ₉ H ₁₆ F ₃ N ₃ 0, 359.1 ; m/z found, 360.1 [M+H] ⁺ . ^! H NMR (400 MHz, DMSO-ofe) δ 9.05 (s, 1 H), 8.90 (s, 1 H), 8.19 (s, 1 H), 8.18 - 8.14 (m, 1 H), 8.05 (d, J = 3.3 Hz, 1 H), 7.88 - 7.79 (m, 2H), 6.85 (d, J = 3.3 Hz, 1 H), 5.21 (s, 2H), 4.28 (t, J = 7.7 Hz, 2H), 3.92 (t, J = 7.7 Hz, 2H), 2.36 - 2.25 (m, 2H).

Example 167: 1 -(Azetidin-1 -yl)-2-r6-r2-methyl-3-

The title compound was prepared in a manner analogous to Example 71 . MS (ESI): mass calcd. for C20H18F3N3O, 373.1 ; m/z found, 374.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-de) δ 8.71 (d, J = 1 .5 Hz, 1 H), 8.61 (s, 1 H), 8.07 (d, J = 3.3 Hz, 1 H), 7.85 (dd, J = 8.0, 1 .3 Hz, 1 H), 7.67 (d, J = 7.2 Hz, 1 H), 7.58 (t, J = 7.7 Hz, 1 H), 6.87 (d, J = 3.2 Hz, 1 H), 5.16 (s, 2H), 4.25 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.34 (d, J = .9 Hz, 3H), 2.33 - 2.24 (m, 2H).

Example 168: ISj-Cyclopropyl-2- 6-(4-fiuorophenyl)pyrrolo[3,2-b]pyridin-1 - yllacetamide.

The title compound was prepared in a manner analogous to Example 75. MS (ES!): mass calcd. for Ci ₈ Hi ₆ FN ₃ 0, 309.1 ; m/z found, 310.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-ds) δ 8.63 (d, J = 2.0 Hz, 1 H), 8.35 - 8.32 (m, 1 H), 8.07 - 8.05 (m, 1 H), 7.80 - 7,74 (m, 2H), 7.63 (d, J = 3.3 Hz, 1 H), 7.37 - 7.31 (m, 2H), 6.60 - 6.57 (m, 1 H), 4.86 (s, 2H), 2.68 - 2.65 (m, 1 H), 0.65 - 0.60 (m, 2H), 0.46 - 0.41 (m, 2H).

Example 169: 1 -(Azetidin-1 -yl)-2-f6-(4-fluoro-3-methyl-phenyl)-3-methyl- pyrroloi3.2-blpyridin-1 -yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C ₂ oH ₂ oFN ₃ G, 337.2; m/z found, 338.2 [M+H] ⁺ . Ή NMR (300 MHz, DMSO) δ 8.59 (s, 1 H), 8.01 (s, 1 H), 7.65 (d, J = 7.2 Hz, 1 H), 7.61 ^■ 7.51 (m, 1 H), 7.36 (s, 1 H), 7.32™ 7.19 (m, 1 H), 4.92 (s, 2H), 4.18 (t, J = 7.6 Hz, 2H), 3.89 (t, J = 7.6 Hz, 2H), 2.33 (s, 3H), 2.31 - 2.18 (m, 5H).

Example 170: 1 -Butyl-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-blpyridine trifluoroacetate salt.

To a solution of 6-(4-fluoro-3-methylphenyl)-1 H-pyrroio[3,2-b]pyridine (60 mg, 0.26 mmol) in DMF (1 .5 mL) at 0 °C was added NaH (14.8 mg, 0.37 mmol, 60% dispersion in oil). The reaction mixture was stirred for 30 minutes, then cooled to 0 °C and 1 -bromobutane (0.22 mL, 0.278 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 hours. The reaction was diluted with methanol to 3 mL, filtered, and purified via HPLC Method C. MS (ESI): mass calcd. for Ci ₈ H ₉ FN ₂ , 282.2; m/z found, 283.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.95 - 8.88 (m, 2H), 8.19 (d, J = 3.2 Hz, 1 H), 7.83 (dd, J = 7.6, 2.5 Hz, 1 H), 7.77 - 7.71 (m, 1 H), 7.35 (dd, J = 9.6, 8.5 Hz, 1 H), 6.80 (dd, J = 3.2, 0.9 Hz, 1 H), 4.43 (t, J = 7.1 Hz, 2H), 2.36 (d, J = 1 ,9 Hz, 3H), 1 ,86 - 1 .75 (m, 2H), 1 .33 - 1 .20 (m, 2H), 0.89 (t, J = 7,3 Hz, 3H).

Example 171 : 6-(4-Fluoro-3-methyl-phenyl)-1 -isopentyl-pyrrolo[3,2-blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 1 -bromo-3-methylbutane and 6-(4~fluoro-3~methylphenyl)~1 H~ pyrrolo[3,2-b]pyridine. MS (ESI): mass calcd. for C19H21 FN2, 296.2; m/z found 297.2 [M+Hf. ¹ H NMR (400 MHz, DMSO-cfe) δ 8.94 (d, J = 1 .6 Hz, 1 H), 8.92 (s, 1 H), 8.22 (d, J = 3.3 Hz, 1 H), 7.86 - 7.81 (m, 1 H), 7.78 - 7.72 (m, 1 H), 7.36 (dd, J = 9.6, 8.6 Hz, 1 H), 6.82 (dd, J = 3.3, 0.8 Hz, 1 H), 4.50 - 4.41 (m, 2H), 2.36 (d, J = 1 .9 Hz, 3H), 1 .78 - 1 .70 (m, 2H), 1 .58 - 1 .48 (m, 1 H), 0.94 (d, J = 6.6 Hz, 6H).

Example 172: 6- blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine and 3- (bromomethyl)pyridine. MS (ESI): mass calcd. for C2oHieFN _3! 317.1 ; m/z found, 318.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 9.03 (s, 1 H), 8.99 - 8.96 (m, 1 H), 8.72 - 8.69 (m, 1 H), 8.58 - 8.53 (m, 1 H), 8.32 (d, J = 3.4 Hz, 1 H), 7.86 - 7.79 (m, 2H), 7.75 - 7.69 (m, 1 H), 7.49 - 7.45 (m, 1 H), 7,38 - 7.32 (m, 1 H), 6.89 (d, J = 3.3 Hz, 1 H), 5.77 (s, 2H), 2.35 (s, 3H).

Example 173: 1 -(Cvclobutylmethyl)-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine and

(bromomethyl)cyclobutane. MS (ESI): mass caicd. for C19H19FN2, 294.2; m/z found, 295.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSG-d ₆ ) δ 8.98 (s, 1 H), 8.95 (d, J = 1 .6 Hz, 1 H), 8.20 (d, J = 3.3 Hz, 1 H), 7.84 (dd, J = 7.3, 2.5 Hz, 1 H), 7.78 - 7.72 (m, 1 H), 7.39 - 7.32 (m, 1 H), 6.81 (d, J = 3.2 Hz, 1 H), 4.47 (d, J = 7.5 Hz, 2H), 2.91 - 2.81 (m, 1 H), 2.36 (d, J = 1 .9 Hz, 3H), 1 .99 - 1 ,77 (m, 6H). Example 174: 1 -(Cyclopropylmethyl)-6-(4-fluoro-3-methyl-phenyl)pyrroioi3,2 - blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 6~(4-fluoro-3~methyiphenyl)~1 H~pyrrolo[3,2-b]pyridine and

(bromomethyi)cyciopropane. MS (ESI): mass calcd. for C18H17FN2, 280,1 ; m/z found, 281 .2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO~cfe) δ 8.95 - 8.90 (m, 2H), 8.22 (d, J = 3.2 Hz, 1 H), 7.84 (dd, J = 7.7, 2.5 Hz, 1 H), 7.77 - 7.71 (m, 1 H), 7.35 (dd, J = 9.6, 8,5 Hz, 1 H), 6.81 (d, J = 3.2 Hz, 1 H), 4.30 (d, J = 7.3 Hz, 2H), 2.36 (d, J = 1 .8 Hz, 3H), 1 .41 - 1 .33 (m, 1 H), 0.58 - 0.52 (m, 2H), 0.49 - 0.44 (m, 2H). -[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-

The title compound was prepared in a manner analogous to Example 375. S (ESI): mass calcd. for C ₈ Hi ₈ FN ₃ G, 31 1 .1 ; m/z found, 312.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-efe) δ 8.99 (s, 1 H), 8.93 (s, 1 H), 8.09 (d, J = 3.3 Hz, 1 H), 7.82 - 7.78 (m, 1 H), 7.74 - 7.68 (m, 1 H), 7.37 (t, J = 9.0 Hz, 1 H), 6.86 (d, J = 3.2 Hz, 1 H), 5.48 (s, 2H), 3.13 (s, 3H), 2.87 (s, 3H), 2.36 (s, 3H). Example 176: 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolof3 _l 2-blpyridin-1 - yij-N-cyclopropyi-acetamide trifluoroacetate salt.

Step A: 3-Chloro-6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-blpyridine. To a solution of 6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine (Example 66, intermediate of Step A, 500 mg, 2.2 mmoi) in DMF (5 mL) cooled at 0 °C was slowly added NCS (384 mg, 2.9 mmol). The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 12 hours. Water was added and it was allowed to stir for 20 minutes. The title

compound was collected via filtration and washed with water (472 mg, 82%). The crude was used without any further purification in the next step. ¹ H NMR (500 MHz, DMSO-cfe) δ 1 1.68 (s, 1 H), 8.67 (s, 1 H), 7.98 (s, 1 H), 7.88 - 7.81 (m, 1 H), 7.67 (d, J = 7.0 Hz, 1 H), 7.61 - 7.52 (m, 1 H), 7.26 (t, J = 9.2 Hz, 1 H), 2.33 (s, 3H).

Step B: 2-r3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolof3.2-blpyridi n-1 -yil-N- cyclopropyl-acetamide trifluoroacetate salt. The title compound was prepared in a manner analogous to Example 136, Step A substituting 2-bromo-N- cyc!opropylacetarnide for 2-bromo-1 -cyclopropylethanone. MS (ESI): mass caicd. for 357.1 ; m/z found, 358.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.74 - 8.71 (m, 1 H), 8.35 - 8.32 (m, 1 H), 8.22 - 8.20 (m, 1 H), 7.86 (d, J = 1 .6 Hz, 1 H), 7.70 (d, J = 7,6 Hz, 1 H), 7,63 - 7.57 (m, 1 H), 7.32 - 7.25 (m, 1 H), 4.90 (s, 2H), 2.68 - 2.62 (m, 1 H), 2.34 (s, 3H), 0.66 - 0.60 (m, 2H), 0.47 - 0.41 (m, 2H).

Example 177: 6-(4-Fluoro-3-methyl-phenyl)-1 -(2-pyridylmethyl)pyrroioi3.2- blpyridine trifiuoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 6-(4~fluoro~3-methyiphenyl)-1 H-pyrrolo[3,2~b]pyridine and 2- (bromomethyi)pyridine. MS (ESI): mass caicd. for C20H16FN3, 317.1 ; m/z found, 318.1 [M+Hf. ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.92 (s, 1 H), 8.89 - 8.85 (m, 1 H), 8.50 - 8.47 (m, 1 H), 8.21 (d, J = 2.4 Hz, 1 H), 7.81 - 7.75 (m, 2H), 7.70 - 7.65 (m, 1 H), 7.36 - 7.26 (m, 3H), 6.84 (d, J = 3.3 Hz, 1 H), 5,79 (s, 2H), 2.33 (d, J = 1 .8 Hz, 3H).

Example 178: (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 -(tetrahydrofuran-3- ylmethyl)pyrroio[3,2-blpyridine trifiuoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-methyiphenyl)-1 H-pyrrolo[3,2-b]pyridine and 3- (bromomethyl)tetrahydrofuran. MS (ESI): mass caicd. for C19H19FN2O, 310.1 ; m/z found, 31 1 .2 [M+Hf. H NMR (400 MHz, DMSO-d ₆ ) δ 8.97 - 8.92 (m, 2H), 8.22 (d, J = 3.3 Hz, 1 H), 7.83 (dd, J = 7.4, 2.5 Hz, 1 H), 7.78 - 7.72 (m, 1 H), 7.39 - 7.31 (m, 1 H), 6.83 (d, J = 3.2 Hz, 1 H), 4.50 - 4.37 (m, 2H), 3.88 3.80 (m, 1 H), 3.70 - 3.60 (m, 2H), 3,51 - 3.43 (m, 1 H), 2.92 - 2.81 (m, 1 H), 2.36 (d, J = 1 .8 Hz, 3H), 1 .94 - 1 .83 (m, 1 H), 1 .69 - 1 .56 (m, 1 H).

Example 179: 6-(4-Fluoro-3-methyl-phenyl)-1 -(4-pyridylmethyl)pyrrolof3,2- blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 2-(chloromethyl)pyridine and 6-(4-fluoro-3-methylphenyl)-1 H- pyrrolo[3,2~b]pyridine. MS (ESI): mass calcd. for C20H16FN3, 317.1 ; m/z found, 318.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.96 (d, J = 1 .7 Hz, 1 H), 8.85 (s, 1 H), 8.63 - 8.58 (m, 2H), 8.24 (d, J = 3.3 Hz, 1 H), 7.77 (dd, J = 7.5, 2.4 Hz, 1 H), 7.70 - 7.65 (m, 1 H), 7.36 - 7.29 (m, 3H), 6.91 (dd, J = 3.3, 0.9 Hz, 1 H), 5.84 (s, 2H), 2.33 (d, J = 1 .9 Hz, 3H). Example 180: (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 -foxiran-2- ylmethyl)pyrrolo[3,2-blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 170. MS (ESI): mass calcd. for C17H15FN2O, 282.1 ; m/z found, 283.1 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-de) δ 8.93 (d, J = 1 .7 Hz, 1 H), 8.84 (s, 1 H), 8.10 (d, J = 3.2 Hz, 1 H), 7.83 - 7.79 (m, 1 H), 7.74 - 7.69 (m, 1 H), 7.35 (t, J = 9.1 Hz, 1 H), 6.83 - 6.79 (m, 1 H), 4.54 (dd, J = 14.5, 3.5 Hz, 1 H), 4.42 - 4.36 (m, 1 H), 3.88 - 3.82 (m, 1 H), 3.41 (dd, J = 10.9, 5.2 Hz, 1 H), 3.27 (dd, J = 10.9, 6.4 Hz, 1 H), 2.36 (s, 3H). -(4-Fluoro-3-methyl-phenyl)-1 -(2-pyrazol-1 -yiethy0pyrrolQf3,2

The title compound was prepared in a manner analogous to Example 170 using 1 -(2-chloroethyl)-1 H-pyrazole and 6-(4-fiuoro-3-methylphenyi)-1 H- pyrrolo[3,2-b]pyridine. MS (ESI): mass caicd. for C19H17FN4, 320.1 ; m/z found, 321 ,2 [M+H] ⁺ . ^! H NMR (500 MHz, DfV SO-d ₆ ) δ 8.87 (d, J = 1 .7 Hz, 1 H), 8.50 (s, 1 H), 7.81 - 7.72 (m, 2H), 7.70 - 7.63 (m, 1 H), 7.42 (d, J = 2.3 Hz, 1 H), 7.39 - 7.32 (m, 2H), 6.73 (d, J = 3.2 Hz, 1 H), 6.08 (t, J = 2.1 Hz, 1 H), 4.85 (t, J = 5.6 Hz, 2H), 4.59 (dd, J = 6.5, 4.5 Hz, 2H), 2.36 (d, J = 1 .9 Hz, 3H).

Example 182: 1 -(Azetidin-1 -yl)-2-[6-(5-chloro-2-thienyl)-3-fluoro-pyrrolo[3,2- blpyridin-1 -yllethanone.

Step A: 1 -(Azetidin-1 -yl)-2-(6-bromo-3-fluoro-1 H-pyrrolof3,2-b]pyridin-1 - yQethanone. The title compound was prepared in a manner analogous to Example 29, Step A. Ή NMR (400 MHz, DMSO-c? ₆ ) δ 8.43 (d, J = 2.0 Hz, 1 H), 8.28 (t, J = 2.1 Hz, 1 H), 7.66 (d, J = 2.2 Hz, 1 H), 4.90 (s, 2H), 4.22 (t, J = 7.6 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.33 - 2.23 (m, 2H).

Step B: 1 -(Azetidin-1 -yl)-2-f6-f5-chloro-2-thienyl)-3-fluoro-pyrrolof3,2- title compound was prepared in a manner analogous to Example 29, Step B, substituting (5-chlorothiophen-2-yl)boronic acid for (3,4~difiuorophenyl)boronic acid. MS (ES!): mass caicd. for

C ieHiaCIFNsOS, 349.0; m/z found, 349.9 [!V1+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.59 (d, J = 1 .8 Hz, 1 H), 8.05 (s, 1 H), 7.49 (d, J = 2.3 Hz, 1 H), 7.33 (d, J = 3.9 Hz, 1 H), 7.04 (d, J = 3.9 Hz, 1 H), 4,94 (s, 2H), 4,36 - 4.28 (m, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.44 - 2.34 (m, 2H).

Example 183: 6-(4-Fluoro-3-methyl-phenyl)-1 -(pyrimidin-2-

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-methyiphenyl)-1 H-pyrrolo[3,2-b]pyridine and 2- (chloromethyl)pyrimidine. MS (ESI): mass calcd. for G19H15FN4, 318.1 ; m/z found, 319.2 [M+H] ^{+ 1} H N MR (500 MHz, CD ₃ OD) δ 8.86 - 8.82 (m, 2H), 8.73 (d, J = 5.0 Hz, 2H), 8.19 (d, J = 3.3 Hz, 1 H), 7.67 (dd, J = 7.2, 2.5 Hz, 1 H), 7.62 - 7.57 (m, 1 H), 7.39 (t, J = 4.9 Hz, 1 H), 7.21 (i, J = 9.0 Hz, 1 H), 6.92 (dd, J = 3.3, 0.9 Hz, 1 H), 5.93 (s, 2H), 2.37 (d, J = 2.0 Hz, 3H).

ylmethyl)pyrrolof3,2-blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Exampl

(ESI): mass calcd. for Ci ₈ H ₁₇ FN ₂ 0, 296.1 ; m/z found, 297.2 [M+H] ⁺ .

-(3,3-Difluoroazetidin-1 -yl)-2-f3-fluoro-6-(4-fluoro-3-methyl-

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3,3- difluoroazeiidin-1 -yl)ethanone (Intermediate 16) and (4-fluoro-3- methylphenyl)boronic acid.. !VIS (ES!): mass calcd, for C19H15F4N3O, 377.1 ; m/z found, 378.0 [M+H] ⁺ . H N MR (500 MHz, DMSO-cfe) δ 8.67 (d, J = 1 .8 Hz, 1 H), 8.16 (t, J = 2.2 Hz, 1 H), 7.70 - 7.65 (m, 1 H), 7.63 (d, J = 2.1 Hz, 1 H), 7.62 - 7.56 (m, 1 H), 7.32 - 7.21 (m, 1 H), 5.08 (s, 2H), 4.73 (t, J = 12.3 Hz, 2H), 4.37 (t, J = 12.6 Hz, 2H), 2.33 (d, J = 1 .9 Hz, 3H).

Example 186: 1 -Cvclopropyl-2-i6-(4-fluoro-3-niethyl-phenyl)pyrroloi3,2- blpyridin-l -yllethanQne trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-niethyiphenyl)-1 H-pyrrolo[3,2-b]pyridine and 2-bromo-1 - cyclopropylethanone. MS (ESI): mass calcd. for C19H17FN2O, 308.1 ; m/z found, 309.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 13.05 (s, 1 H), 9.05 (s, 1 H), 8.85 (s, 1 H), 8.33 - 8.28 (m, 1 H), 7.81 - 7.76 (m, 1 H), 7.72 - 7.66 (m, 1 H), 7.38 (t, J = 9.1 Hz, 1 H), 7.02 (s, 1 H), 6.12 (s, 2H), 2.41 - 2.31 (m, 4H), 1 .18 - 1 .1 1 (m, 2H), 1 .08 - 1 .00 (m, 2H). -[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-3-

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine and 1 -bromo-3- methylbutan-2-one. MS (ESI): mass calcd. for C19H19FN2O, 310,1; m/z found, 311.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 13.03 (s, 1H), 9.01 (d, J = 1.5 Hz, 1 H), 8.87 - 8.84 (m, 1 H), 8.32 (t, J = 3.1 Hz, 1 H), 7.78 (dd, J = 7.8, 2.4 Hz, 1 H), 7.73 - 7.66 (m, 1 H), 7.43 - 7.36 (m, 1 H), 7.00 - 6.96 (m, 1 H), 6.05 (s, 2H), 3.05-2,97 (m, 1H), 2.36 (d, J= 1.9 Hz, 3H), 1.21 (d, J = 6.9 Hz, 6H).

Example 188: 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-1 -(4- hydroxy-l-piperidyDethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C ₂ H ₂₂ F!M ₃ 0 ₂ , 367.2; m/z found, 368.2 [M+H] ⁺ . H NMR (500 MHz, DMSO-d ₆ ) δ 8.97 (d, J = 1.5 Hz, 1H), 8.91 (s, 1H), 8.11 (d, J = 3.3 Hz, 1H), 7.79 (dd, J = 7.4, 2.5 Hz, 1H), 7.73-7.68 (m, 1H), 7.37 (t, J = 9.1 Hz, 1H), 6.86 (d, J = 3.3 Hz, 1H), 5.51 (s, 2H), 3.87-3.74 (m, 4H), 3.12- 3.04 (m, 2H), 2.35 (d, J = 1 ,8 Hz, 3H), 1 ,92 - 1.85 (m, 1 H), 1.76 - 1.68 (m, 1 H), 1.58 - 1.50 (m, 1 H), 1.35 - 1.26 (m, 1 H). -(3-Azabicycloi3.1.01hexan-3-vn-2-r6-f4-fluoro-3-

The title compound was prepared in a manner analogous to Example 86. MS (ESI): mass calcd. for C21H20FN3O, 349.2; m/z found, 350.2 [M+H] ⁺ . 'H NMR (500 MHz, DMSO-cfe) δ 8.92 (s, 1 H), 8.79 (s, 1 H), 8.01 (d, J = 3.4 Hz, 1 H),

7.76 (dd, J = 7.2, 2.4 Hz, 1 H), 7.71 - 7.65 (m, 1 H), 7.35 (t, J = 9.1 Hz, 1 H), 6.81 (d, J = 3.2 Hz, 1H), 5.37 (d, J = 17,3 Hz, 1H), 5.24 (d, J= 17.2 Hz, 1H),

3.77 - 3.68 (m, 2H), 3.57 (d, J = 11.6 Hz, 2H), 2.35 (s, 3H), 1.77 - 1.70 (m, 1H), 1.62-1.55 (m, 1H), 0.81 -0.73 (m, 1H), 0.24 - 0.19 (m, 1H).

Example 190: 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-1 ~(4- methoxy-1-piperidyl)ethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C22H24FN3G2, 381.2; m/z found, 382.2 [M+H] ⁺ . ¹ H NMR (500 MHz, CDCI ₃ ) 8.81 (d, J = 1.7 Hz, 1H), 8.19 (s, 1H), 7.54 (d, J = 3.3 Hz, 1H), 7.38-7.35 (m, 1H), 7.34-7.29 (m, 1H), 7.10 (t, J= 8.8 Hz, 1H), 6.86 (dd, J = 3.3, 0,9 Hz, 1 H), 5.22 (d, J = 16.9 Hz, 1 H), 5.14 (d, J = 16.9 Hz, 1 H), 3.80 - 3.72 (m, 2H), 3.56 - 3.49 (m, 2H), 3.48 - 3.41 (m, 1 H), 3.38 (s, 3H), 2.34 (d, J = 1.9 Hz, 3H), 1.99 - 1 ,90 (m, 1 H), 1.88 - 1.80 (m, 1 H), 1.80 - 1.72 (m, 1H), 1.70-1.62 (m, 1H). -[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-1 -(4-

The title compound was prepared in a manner analogous to Example 86, MS (ESI): mass calcd. for C21H21F2N3O, 369.2; m/z found, 370.2 [M+H] ^{+ 1} H NMR (500 MHz, CDCI3) δ 8.66 (d, J = 1.6 Hz, 1 H), 8.20 (s, 1 H), 7.56 (d, J = 3,4 Hz, 1 H), 7.38 (dd, J = 7.0, 2.4 Hz, 1 H), 7.36 - 7.31 (m, 1 H), 7.12 (t, J = 8.7 Hz, 1 H), 6.94 - 6.91 (m, 1 H), 5.23 (d, J = 16.8 Hz, 1 H), 5.16 (d, J = 16.8 Hz, 1 H), 5.04 - 4.87 (m, 1 H), 4.04 - 3.96 (m, 1 H), 3.77 - 3.68 (m, 1 H), 3.67 - 3.59 (m, 1H), 3.50-3.40 (m, 1H), 2.35 (d, J = 1.9 Hz, 3H), 2.11 -2.02 (m, 1H), 2.01 - 1.87 (m, 2H), 1.86-1.78 (m, 1H).

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C22H23F2N3O, 383.2; m/z found, 384.2 [M+H] ⁺ . H NMR (500 MHz, CDCI3) δ 8.57 (s, 1 H), 8.25 (s, 1 H), 7.57 (d, J = 3.2 Hz, 1 H), 7.37 - 7.34 (m, 1H), 7.34-7.29 (m, 1H), 7.10 (t, J= 8,7 Hz, 1H), 6,82 (d, J = 3,2 Hz, 1 H), 5.24 (d, J ~ 17.0 Hz, 1 H), 5.19 (d, J = 17.0 Hz, 1 H), 4.58 (d, J = 13.5 Hz, 1H), 4.43-4.34 (m, 1H), 4.33-4.24 (m, 1H), 3.97 (d, J = 13.8 Hz, 1H), 3.33 - 3.23 (m, 1 H), 2.77 - 2.67 (m, 1 H), 2.33 (d, J = 1.9 Hz, 3H), 2.09 - 1.91 (m, 2H), 1.80 (d, J= 13.5 Hz, 1H), 1.49-1.38 (m, 1H), 1.37-1.26 (m, 1H),

The title compound was prepared in a manner analogous to Example 66. S (ESI): mass calcd. for C21 H22FN3G, 351 .2; m/z found, 352.2 [M+H] ⁺ . Analytical HPLC was obtained on a Agilent 1 100 Series using an !nertsil ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min

(Temperature = 50 °C). R _t = 0,95 min at 254 nm.

Example 194: (R/S)-2-f6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3 _l 2-b]pyridin-1 vn-1 -(2-methylmorpholin-4-yl)ethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C21 H22FN3O2, 367.2; m/z found, 368.2 [M+H] ⁺ .

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsii ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C). R _t = 0.89 min. at 254 nm. -2-r6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 88. MS (ESI): mass calcd. for C ₂₂ H ₂ i F ₄ N ₃ 0, 41 9.2; m/z found, 420.2 [M+H] ⁺ .

Analytical H P LC was obtained on a Agilent 1 1 00 Series using an Inertsii ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C). F¾ = 1 .03 min at 254 nm.

Example 1 96: (R/S)-1 -(2-Ethylpyrrolidin-1 -yl)-2-f6-(4-fluoro-3-methyl- phenv0pyrrolof3,2-blpyridin-1 -yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 88. MS (ES!): mass calcd. for C22H24FN3O, 365.2; m/z found, 368.2 [!V1H-H] ^÷ . Analytical H PLC was obtained on a Agilent 1 1 00 Series using an Inertsii ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min

(Temperature = 50 °C). Rt = 0.99 min at 254 nm. -(2,2-Dimethylmorpholin-4-yl)-2-f6-(4-fluoro-3-methyl'

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C22H24FN3O2, 381 .2; m/z found, 382.2 [M+H] ⁺

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsii ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 niL/min (Temperature = 50 °C). F¾ = 0.91 min at 254 nm.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C21 H22FN3O2, 367.2; m/z found, 368.2 [M+H] ⁺ .

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsii ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 niL/min (Temperature = 50 °C). F¾ = 0.88 min at 254 nm. -2-r6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C21 H21 F2N3O, 369.2; m/z found, 370.2 [M+H] ⁺

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 rnL/min (Temperature = 50 °C). F¾ = 0.92 min at 254 nm.

Example 200: 1 -(2,2-Dimethylpyrrolidin-1 -yl)-2-f6-(4-fluoro-3-methyl- phenyl)pyrroioi3,2-blpyridin-1 -yllethanone trifiuoroacetate salt.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C22H24FN3O, 365.2; m/z found, 366.2 [M+H] ⁺ . Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min

(Temperature = 50 °C). Rt = 1 .00 min at 254 nm. Example 201 : 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-1 ^■

The title compound was prepared in a manner analogous to Example 86, MS (ESI): mass calcd. for C20H19F2N3O, 355.1 ; m/z found, 356.2 [M+H] ⁺

Analytical HPLC was obtained on a Agilent 1 100 Series using an !nertsii ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C). f¾ = 1 .31 min at 254 nm.

Exam le 202: 2-i6-(4-Fluorophenyl)pyrroloi3,2-b]pyridin-1 -yll-1 -(3-hydroxy-3-

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for Ci ₉ Hi ₈ F ₃ 02, 339.1 ; m/z found, 340.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.64 (d, J = 2.0 Hz, 1 H), 8.1 1 - 8.08 (m, 1 H), 7.82 - 7.75 (m, 2H), 7.61 (d, J = 3,3 Hz, 1 H), 7.39 - 7.30 (m, 2H), 6.61 (dd, J = 3,2, 1 .0 Hz, 1 H), 5.69 (s, 1 H), 5.04 (s, 2H), 4.07 - 3.99 (m, 2H), 3.80 - 3.69 (m, 2H), 1 .40 (s, 3H). -[6-(4-Fluorophenyl)pyrrolof3,2-blpyridin-1 -yll-1 -i3-hvdroxy-3-

The title compound was prepared in a manner analogous to Example 86. MS (ESi): mass calcd. for C19H15F4N3O2, 393.1; m/z found, 394.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-de) δ 8.64 (d, J ^2.0 Hz, 1H), 8.11 -8.08 (m, 1H), 7.80- 7.74 (m, 2H), 7.63 (d, J = 3.3 Hz, 1 H), 7.51 (s, 1 H), 7.38 - 7.30 (m, 2H), 6.62 (dd, J= 3.3, 0.9 Hz, 1H), 5.12 (s, 2H), 4.47 (d, J = 10.0 Hz, 1H), 4.24 (d, J = 9.9 Hz, 1H), 4.14 (d, J = 10.8 Hz, 1H), 3.91 (d, J = 10.8 Hz, 1H).

Exam le 204: 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(4-fluorophenyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C18H15F2N3O, 327.1; m/z found, 328.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.64 (d, J = 1.9 Hz, 1H), 8.12-8.08 (m, 1H), 7.81 - 7.74 (m, 2H), 7.60 (d, J = 3.3 Hz, 1 H), 7.38 - 7.30 (m, 2H), 6.61 (dd, J = 3.2, 0.9 Hz, 1 H), 5.55 - 5.35 (m, 1 H), 5.07 (d, J = 2.3 Hz, 2H), 4.61 - 4.45 (m, 1 H), 4.38-4.17 (m, 2H), 4.04-3.88 (m, 1H). -Cvclopropyl-2-f6-(4-fluorophenyl)pyrrolor3,2-blpyridin-1 -yl

The title compound was prepared in a manner analogous to Example 88. MS (ESi): mass calcd. for C19H18FN3O, 323.1 ; m/z found, 324.2 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-de) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.09 (s, 1 H), 7.82 - 7.74 (m, 2H), 7.62 (d, J = 3.2 Hz, 1 H), 7.37 - 7.29 (m, 2H), 8.58 (d, J = 3.3 Hz, 1 H), 5.35 (s, 2H), 3.00 - 2.95 (m, 1 H), 2.83 (s, 3H), 1 .02 - 0.95 (m, 2H), 0.93 (dd, J = 7.0, 4.8 Hz, 2H).

Exam le 208: 2-[6-(4-Fluorophenyl)pyrrolo[3,2-blpyridin-1 -yil-1 -[3-

The title compound was prepared in a manner analogous to Example 86. MS (ESI): mass calcd. for C ₉ Hi ₈ FfM ₃ 0 ₂ , 339.1 ; m/z found, 340.2 [M+H] ⁺ . H !MMR (500 MHz, DMSO-cfe) δ 8,65 - 8.61 (m, 1 H), 8.10 - 8.06 (m, 1 H), 7.81 - 7.75 (m, 2H), 7.61 - 7.58 (m, 1 H), 7.37 - 7.30 (m, 2H), 6.59 (d, J = 3.3 Hz, 1 H), 5.01 (s, 2H), 4.83 (t, J = 5.1 Hz, 1 H), 4.20 (t, J = 8.3 Hz, 1 H), 3.98 - 3.86 (m, 2H), 3.65 - 3.60 (m, 1 H), 3.57 - 3.51 (m, 2H), 2.77 - 2.67 (m, 1 H). -[6-(4-Fluorophenyl)pyrrolof3,2-blpyridin-1 -yll-1 -(3

The title compound was prepared in a manner analogous to Example 86. MS (ES!): mass calcd. for Ci ₉ Hi ₈ F ₃ 02, 339.1 ; m/z found, 340.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ofe) δ 8.65 - 8.61 (m, 1 H), 8.1 1 - 8.06 (m, 1 H), 7.82 - 7.74 (m, 2H), 7,62 - 7.57 (m, 1 H), 7.37 - 7.30 (m, 2H), 6.61 - 6.58 (m, 1 H), 5.04 (s, 2H), 4.41 - 4.34 (m, 1 H), 4.29 - 4.22 (m, 1 H), 4.1 1 - 4.02 (m, 2H), 3.75 - 3.68 (m, 1 H), 3.23 (s, 3H).

Example 208: 1 -(5-Azaspiro[2.3]hexan-5-yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolof3,2-blpyridin-1 -yllethanone frifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C ₂ H ₂ oFfM ₃ 0, 349.2; m/z found, 350.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 9,00 (s, 1 H), 8,96 (s, 1 H), 8.1 1 (d, J = 3.2 Hz, 1 H), 7.83 - 7.79 (m, 1 H), 7.75 - 7.69 (m, 1 H), 7.38 (t, J = 9.1 Hz, 1 H), 6.87 (d, J = 3.3 Hz, 1 H), 5.29 (s, 2H), 4.35 (s, 2H), 3.99 (s, 2H), 2.36 (s, 3H), 0.74 - 0.65 (m, 4H), -[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-1 -(4-

The title compound was prepared in a manner analogous to Example 86, MS (ESI): mass calcd. for C22H24FN3G2, 381 .2; m/z found, 382.2 [M+H] ⁺ -2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C21 H22FN3G2, 367.2; m/z found, 368.2 [M+H] ⁺ .

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsii ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 niL/min (Temperature = 50 °C). R _t = 0.88 min at 254 nm.

Example 21 1 : 2-[6-(4-Fluorophenyl)pyrrolo 3,2-b]pyridin-1 -yi]-1 -(3- hydroxyazetidin-1 -vQethanone.

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for Ci ₈ Hi ₆ F ₃ 02, 325.1 ; m/z found, 326.2 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 8.63 (d, J = 2.0 Hz, 1 H), 8.10 - 8.08 (m, 1 H), 7.80 - 7.76 (m, 2H), 7.60 (d, J = 3,3 Hz, 1 H), 7.36 - 7.31 (m, 2H), 6.61 - 6.59 (m, 1 H), 5.78 (d, J = 5.7 Hz, 1 H), 5.03 (d, J = 2.8 Hz, 2H), 4.55 - 4.47 (m, 1 H), 4.38 - 4.33 (m, 1 H), 4.12 - 4.07 (m, 1 H), 3.96 - 3.91 (m, 1 H), 3,65 - 3.61 (m, 1 H).

Example 212: 1 -[2-f6-(4-Fluorophenyl)pyrrolo[3,2-blpyridin-1

yllacetyllazetidine-3-carbonitrile.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for Ci ₉ H ₁₅ FN ₄ G, 334.1 ; m/z found, 335.1 [M+H] ⁺ . Ή NMR (400 MHz, DMSO-d ₆ ) δ 8.64 (d, J = 2.0 Hz, 1 H), 8.1 1 - 8.08 (m, 1 H), 7.81 - 7.75 (m, 2H), 7.59 (d, J = 3,3 Hz, 1 H), 7.37 - 7.31 (m, 2H), 6.61 (dd, J = 3,3, 0.9 Hz, 1 H), 5.05 (s, 2H), 4.52 - 4.36 (m, 1 H), 4.23 - 4.16 (m, 1 H), 4.12 - 4.01 (m, 2H), 3.91 - 3.81 (m, 1 H).

b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for C18H14F3N3O, 345.1 ; m/z found, 346.2 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-cfe) δ 8.64 (d, J = 2.0 Hz, 1 H), 8.12 - 8.10 (m, 1 H), 7.80 - 7.75 (m, 2H), 7.59 (d, J = 3.3 Hz, 1 H), 7.37 - 7.31 (m, 2H), 6.62 (dd, J = 3.3, 0.9 Hz, 1 H), 5.14 (s, 2H), 4.75 - 4.68 (m, 2H), 4.41 - 4.33 (m, 2H). Example 214: 2-[6-(4-Fluorophenyl)pyrrolo[3,2-blpyridin-1 -yl]-1 -(3-

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for C19H18FN3O, 323.1 ; m/z found, 324.2 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-cfe) δ 8.63 (d, J = 2.0 Hz, 1 H), 8.10 - 8.08 (m, 1 H), 7.80 - 7.76 (m, 2H), 7.60 (d, J = 3.3 Hz, 1 H), 7.37 - 7.31 (m, 2H), 6.60 (dd, J = 3.3, 0.9 Hz, 1 H), 5.00 (s, 2H), 4.30 (t, J = 8.4 Hz, 1 H), 4.01 (t, J = 8.9 Hz, 1 H), 3.76 (dd, J = 8.4, 5.6 Hz, 1 H), 3.46 (dd, J = 9.5, 5.6 Hz, 1 H), 2.77 - 2.68 (m, 1 H), 1 .21 (d, J = 6.9 Hz, 3H).

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C20H20FN3O, 337.2; m/z found, 338.2 [M+H] ⁺ . Ή NMR (500 MHz, DMSO-ds) δ 8.64 (d, J = 2.0 Hz, 1 H), 8.12 (s, 1 H), 7.81 - 7.75 (m, 2H), 7.62 (d, J = 3.3 Hz, 1 H), 7.37 - 7.30 (m, 2H), 6.60 (d, J = 3.3 Hz, 1 H), 5.02 (s, 2H), 3.88 (s, 2H), 3.59 (s, 2H), 1 ,25 (s, 6H). -[2-f6-(4-Fluorophenyl)pyrrolor3,2-blpyridin-1

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C19H16F 3O2, 337.1 ; m/z found, 338.1 [M+H] ⁺ .

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0,4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C). F¾ = 0.75 min at 254 nm.

Example 217: 1 -(3,3-Difiuoropyrroiidin-1 -yl)-2-[6-(4-fluorophenyl)pyrrolo 3,2- blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C19H16F3N3O, 359.1 ; m/z found, 360.1 [M+H] ⁺ . H !MMR (500 MHz, DMSO-cfe) δ 8,63 (s, 1 H), 8.1 1 (s, 1 H), 7.80 - 7.73 (m, 2H), 7.60 - 7.56 (m, 1 H), 7.37 - 7.30 (m, 2H), 6.62 - 6.58 (m, 1 H), 5.26 (s, 1 H), 5.19 (s, 1 H), 4.13 (t, J = 13.2 Hz, 1 H), 3.90 (t, J = 7.4 Hz, 1 H), 3.74 (t, J = 13.2 Hz, 1 H), 3.57 (t, J = 7.4 Hz, 1 H), 2.64 - 2.53 (m, 1 H), 2,46 - 2,38 (m, 1 H). -2-f6-(4-Fluorophenyl)pyrrolof3.2-blpyridin-1 -yll-1 -(3-

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for dgHigFNaOa, 339.1 ; m/z found, 340.2 [M+H] ⁺ .

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 rnL/min (Temperature = 50 °C). F¾ = 0.72 min at 254 nm.

Example 219: 1 -Cvclopropyl-2-f6-(m-tolyl)pyrrolof3,2-blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 75. MS (ES!): mass calcd. for Ci ₉ Hi ₈ N ₂ 0, 290.1 ; m/z found, 291 .2 [M+H] ⁺ . H NMR (400 MHz, DMSO-de) δ 8.64 (d, J = 1 .9 Hz, 1 H), 8.08 - 8.05 (m, 1 H), 7.60 (d, J = 3.3 Hz, 1 H), 7,55 (s, 1 H), 7.52 (d, J = 7.6 Hz, 1 H), 7.37 (t, J = 7.6 Hz, 1 H), 7.19 (d, 7.7 Hz, 1 H), 6.60 (dd, J = 3.2, 0.9 Hz, 1 H), 5.48 (s, 2H), 2.40 (s, 3H), 2.13 - 2.06 (m, 1 H), 1 .01 - 0.91 (m, 4H). Example 220: 1 -Cyclopropyl-2-(6-phenylpyrrolo[3,2-b]pyridin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 75. MS (ES!): mass calcd. for Ci ₈ Hi ₆ N ₂ 0, 276.1; m/z found, 277.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.66 (d, J = 2.0 Hz, 1H), 8.10-8.08 (m, 1H), 7.77- 7.71 (m, 2H), 7.61 (d, J = 3,3 Hz, 1 H), 7,53 - 7.47 (m, 2H), 7.41 - 7.35 (m, 1 H), 6.61 (dd, J = 3.3, 0.9 Hz, 1 H), 5.48 (s, 2H), 2.14 - 2.06 (m, 1 H), 1.02 - 0.91 (m, 4H).

Example 221 : 1 -Cyclopropyl-2-r6-(3-fluorophenyl)pyrrolof3,2-blpyridin-1 - yllethanone.

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for Ci ₈ Hi ₅ FN ₂ 0, 294.1; m/z found, 295.1 [M+H] ⁺ . Ή NMR (500 MHz, DMSO-cfe) δ 8.70 (d, J = 2.0 Hz, 1H), 8.19-8.17 (m, 1H), 7.65- 7.59 (m, 3H), 7.56-7.50 (m, 1H), 7.23-7.17 (m, 1H), 6.62 (dd, J = 3.2, 0.9 Hz, 1H), 5.48 (s, 2H), 2.14-2.07 (m, 1H), 1.02-0.96 (m, 2H), 0.96-0.91 (m, 2H).

Example 222: 1 -Cvclopropyl-2-f6-(4-fluorophenyl)pyrrolof3,2-blpyridin-1 - yllethanone.

The title compound was prepared in a manner analogous to Example /5. MS (ES!): mass calcd. for CisHisFNaO, 294.1; m/z found, 295.1 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-cfe) δ 8.63 (d, J ^2.0 Hz, 1H), 8.10-8.07 (m, 1H), 7.80- 7.74 (m, 2H), 7.61 (d, J = 3.3 Hz, 1 H), 7.35 - 7.30 (m, 2H), 6.61 (dd, J = 3.3, 0.9 Hz, 1H), 5.47 (s, 2H), 2.13-2.06 (m, 1H), 1.01 -0.96 (m, 2H), 0.96- 0.92 (m, 2H). methyl-butan-2-one.

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C ₂ oH ₂ i FN ₂ G, 324.2; m/z found, 325.2 [M+H] ⁺ . Ή !MIV!R (400 MHz, DMSO-cfe) δ 8.24 (d, J = 1 .9 Hz, 1 H), 7.70 - 7.67 (m, 1 H), 7.57 (d, J = 3.3 Hz, 1 H), 7.15 - 7.05 (m, 2H), 6.62 (dd, J = 3.3, 0.9 Hz, 1 H), 5.36 (s, 2H), 2.84 - 2.75 (m, 1 H), 2.22 (d, J = 2.1 Hz, 3H), 2.15 (s, 3H), 1 .10 (d, J = 7.0 Hz, 6H).

Example 224: 1 -[6-(3-Ethylphenyl)pyrrolof3,2-blpyridin-1 -yll-3-methyl-butan-

2~one.

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C20H22N2O, 306.2; m/z found, 307.2 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-d ₆ ) δ 8.64 (d, J = 2.0 Hz, 1 H), 8.02 - 8.00 (m, 1 H), 7.57 (d, J = 3.3 Hz, 1 H), 7.56 - 7.54 (m, 1 H), 7.54 - 7.50 (m, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.24 - 7.20 (m, 1 H), 6.61 (dd, J = 3.3, 0.9 Hz, 1 H), 5.42 (s, 2H), 2.88 - 2.79 (m, 1 H), 2.69 (q, J = 7.6 Hz, 2H), 1 .24 (t, J = 7.6 Hz, 3H), 1 .13 (d, J = 6.9 Hz, 6H). Example 225: 1 -i6-(2.3-Dimethviphenyl)pyrroioi3,2-blpyridin-1 -νΙΙ-3-methyl· buian-2~one.

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C20H22N2O, 306.2; m/z found, 307.2 [M+H] ⁺ H NMR (400 MHz, DMSO-de) δ 8.28 (d, J = 1 .8 Hz, 1 H), 7.75 (s, 1 H), 7.60 (d, J = 3.3 Hz, 1 H), 7.23 - 7.14 (m, 2H), 7.09 (dd, J = 7.3, 1 .8 Hz, 1 H), 6.64 - 6.62 (m, 1 H), 5.38 (s, 2H), 2.84 - 2.75 (m, 1 H), 2.31 (s, 3H), 2.12 (s, 3H), 1 .10 (d, J = 6.9 Hz, 6H).

ethanone.

a solution a 6-bromo- 1 H-pyrrolo[3,2-b]pyridine (5 g, 25 mmoi) in dioxane (100 mL) was added 4- fluorophenyiboronic acid (4.26 g, 30.5 mmoi), Pd(dppf)CI ₂ (1 .86 g, 2.54 mmol), CS2CO3 (24,8 g, 76.1 mmoi) and water (10 mL). After 16 hours at 90 °C the reaction mixture cooled and was concentrated under reduced pressure. Purification (FCC, S1O2, 0-100% EtOAc in hexanes) afforded the title compound (5.3 g, 98%). MS (ES!): mass calcd. for C13H9FN2, 212.1 ; m/z found, 213.1 [M+H] ⁺ .

Step B: 2-i6-(4-Fluorophenyl)pyrroloi3,2-b]pyridin-1 -yll-1 -phenyl-ethanone.

To a solution of 6-(4-fluorophenyl)-1 H-pyrroio[3,2-b]pyridine (100 mg, 0.471 mmol) in anhydrous DMF (5 mL) was added NaH (60% dispersion, 26 mg, 0.66 mmol) at 0 °C in small portions under argon. The reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was cooled to 0 °C and to the mixture was added 2-bronioacetophenone (98 mg, 0.495 mmol) in small portions. The reaction mixture was warmed to room temperature and the stirring was continued for 12 h. Water was added to the reaction mixture and the reaction extracted with EtOAc. The organic layers were combined, dried, filtered, and concentrated. Purification by HPLC Method C provided the title compound. MS (ESI): mass calcd. for C21 H15FN2O, 330.1 ; m/z found, 331 .2 [ +H] ⁺ , ¹ H NMR (500 MHz, D SO-d ₆ ) δ

8.70 - 8.60 (s, 1 H), 8.28 - 8.18 (s, 1 H), 8.14 - 7.98 (m, 2H), 7.83 - 7.70 (m, 3H), 7.70 - 7.57 (m, 3H), 7.36 - 7.19 (m, 2H), 6.72 - 6.57 (d, J = 3.4 Hz, 1 H), 6.1 1 - 5.94 (s, 1 H).

Example 227: 1 -(4-Fluorophenyl)-2-[6-(4-fluorophenyl)pyrrolof3,2-blpyridin -1 -

The title compound was prepared in a manner analogous to Example 226. MS (ES!): mass calcd. for C21 H14F2N2O, 348.1 ; m/z found, 349.1 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.66 (d, J = 2.0 Hz, 1 H), 8.22 - 8.20 (m, 1 H), 8.20 - 8.17 (m, 2H), 7.79 - 7.75 (m, 2H), 7.65 (d, J = 3.3 Hz, 1 H), 7.49 - 7.44 (m, 2H), 7.32 - 7.27 (m, 2H), 6.65 (dd, J = 3.2, 0.9 Hz, 1 H), 6.02 (s, 2H).

Example 228: (R/S)-6-(4-Fluorophenyl)-1 -(tetrahydropyran-2- ylmethyl)pyrrolof3,2-blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 226. MS (ESI): mass calcd. for C19H19FN2O, 310.1 ; m/z found, 31 1 .2 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 9.01 (br. s, 1 H), 8.86 (s, 1 H), 8.06 (s, 1 H), 7.95 - 7.89 (m, 2H), 7.47 - 7.39 (m, 2H), 6.80 (s, 1H), 4.50 (dd, J = 14.6, 3.5 Hz, 1 H), 4.41 (dd, J = 14.6, 7.8 Hz, 1 H), 3.84 - 3.79 (m, 1 H), 3.70 - 3.63 (m, 1 H), 3.30 -3.22 (m, 1H), 1.78 (d, J = 12.2 Hz, 1H), 1.70-1.64 (m, 1H), 1,52-1.36 (m, 3H), 1.25-1.13 (m, 1H).

Example 229: 2-f6-(4-Fluarophenyl)pyrrQlQ[3,2~b]pyridin-1 -yll-N-isopropyi- acetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for 311.1; m/z found, 312.2 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-cfe) δ 8.63 (s, 1H), 8.16 (d, J = 7.8 Hz, 1H), 8.07 (s, 1H), 7.81 - 7.72 (m, 2H), 7.63 (s, 1 H), 7.34 (t, J = 8.4 Hz, 2H), 6.59 (s, 1 H), 4.87 (s, 2H), 3.88 - 3.79 (m, 1 H), 1.08 (d, J = 6.6 Hz, 6H).

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for 311.1; m/z found, 312.2 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-cfe) δ 8.64 (d, J ^2.0 Hz, 1H), 8.18 (t, J = 5.6 Hz, 1H), 8.08 - 8.06 (m, 1 H), 7.80 - 7.73 (m, 2H), 7.64 (d, J = 3.3 Hz, 1 H), 7.37 - 7.31 (m, 2H), 6.59 (d, J = 3.2, 0.9 Hz, 1 H), 4.91 (s, 2H), 3.05 (q, J = 6.6 Hz, 2H), 1.47 - 1.38 (m, 2H), 0.83 (t, J = 7.4 Hz, 3H). -2-f6-(4-Fluorophenyl)pyrrolof3.2-blpyridin-1 -yl1-N-(2.2.2-

The title compound was prepared in a manner analogous to Example 86. MS (ESI): mass calcd. for C18H15F4N3O, 365.1 ; m/z found, 366.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.91 (d, J = 8.8 Hz, 1 H), 8.64 (d, J = 2.0 Hz, 1 H), 8.05 - 8.03 (m, 1 H), 7.79 - 7.73 (m, 2H), 7.65 (d, J = 3.3 Hz, 1 H), 7.38 - 7.30 (m, 2H), 6.60 (dd, J = 3.3, 0.8 Hz, 1 H), 5.02 (s, 2H), 4.65 - 4.53 (m, 1 H), 1 .28 (d, J = 7.0 Hz, 3H).

Exam le 232: 2-f6-(4-Fluorophenyl)pyrrolo[3,2-blpyridin-1 -yll-N-( 1 -

The title compound was prepared in a manner analogous to Example 66. MS

(ESI): mass calcd. for Ci ₉ Hi ₈ FN ₃ 0, 323.1 ; m/z found, 324.2 [M+H] ⁺ . Ή !MIV!R (500 MHz, DMSO-cfe) δ 8.63 (d, J = 2.0 Hz, 1 H), 8.50 (s, 1 H), 8.05 - 8.02 (m, 1 H), 7.79 - 7.73 (m, 2H), 7.62 (d, J = 3.2 Hz, 1 H), 7.38 - 7.31 (m, 2H), 6.59 (dd, J = 3.3, 0.9 Hz, 1 H), 4.82 (s, 2H), 1 .26 (s, 3H), 0.65 - 0.60 (m, 2H), 0.55 - 0.51 (m, 2H). -(2-Fluoroethyl)-2-f6-(4-fluorophenyl)pyrrolor3,2-blpyridin- 1 -

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C17H15F2N3O, 315.1 ; m/z found, 316.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.64 (s, 1 H), 8.50 (t, J = 5.7 Hz, 1 H), 8.10 - 8.06 (m, 1 H), 7.81 - 7.74 (m, 2H), 7.65 (d, J = 3.3 Hz, 1 H), 7.37 - 7.30 (m, 2H), 6.62 - 6.59 (m, 1 H), 4.97 (s, 2H), 4.50 (t, J = 5.0 Hz, 1 H), 4.39 (t, J = 4.9 Hz, 1 H), 3.47 - 3.41 (m, 2H).

Example 234: 2-i6-(4-Fluorophenyl)pyrroloi3.2-b]pyridin-1 -yll-N-isobutyl acetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for 325.2; m/z found, 326.2 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-C ) δ 8.63 (d, J = 2.0 Hz, 1 H), 8.19 (t, J = 5.8 Hz, 1 H), 8.07 (dd, J = 1 .9, 0.8 Hz, 1 H), 7.80 - 7.73 (m, 2H), 7.65 (d, J = 3.3 Hz, 1 H), 7.38 - 7.30 (m, 2H), 6.59 (dd, J = 3.2, 0.9 Hz, 1 H), 4.93 (s, 2H), 2.92 (t, J = 6.3 Hz, 2H), 1 .75 - 1 .63 (m, 1 H), 0.83 (d, J = 6.7 Hz, 6H).

-ii6-(4-Fluoro-3-methvi-phenyl)pyrroloi3,2-blpyridin-1

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fiuoro-3-methylphenyi)-1 H-pyrrolo[3,2-b]pyridine and 5- (chioromethyl)-3-methyl-1 ,2,4-oxadiazoie, MS (ESI): mass calcd. for

Ci ₈ Hi ₅ FN ₄ 0, 322.1 ; m/z found, 323.1 [M+H] ⁺ . ¹ H N MR (400 MHz, DMSO-d ₆ ) δ 8.68 (d, J = 2.0 Hz, 1 H), 8.29 - 8.25 (m, 1 H), 7.79 (d, J = 3.5 Hz, 1 H), 7.71 - 7.66 (m, 1 H), 7.62 - 7.55 (m, 1 H), 7.26 (dd, J = 9.7, 8.5 Hz, 1 H), 6.68 (dd, J = 3.3, 0.9 Hz, 1 H), 5.96 (s, 2H), 2.32 (d, J = 1 .9 Hz, 3H), 2.27 (s, 3H).

Example 236: 6-(4-Fiuoro-3-methyi-phenyi)-1 -methylpyrazol-4- yl)niethyl]pyrroloi3,2-blpyridine.

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine and 4- (chloromethyl)-1 ~methyi-1 H-pyrazole. MS (ESI): mass calcd. for C19H17FN4, 320.1 ; m/z found, 321 .2 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-d ₆ ) δ 8.61 (d, J = 2.0 Hz, 1 H), 8.22 - 8.19 (m, 1 H), 7,72 (d, J = 3.2 Hz, 1 H), 7.70 - 7.66 (m, 1 H), 7.61 - 7.55 (m, 2H), 7.26 (dd, J = 9.7, 8.5 Hz, 1 H), 6.57 (dd, J = 3.3, 0.9 Hz, 1 H), 6.14 (d, J = 2.1 Hz, 1 H), 5,41 (s, 2H), 3,77 (s, 3H), 2,33 (d, J = 2.0 Hz, 3H). -(Cvclopropylmethyl)-2-[6-(4-fluorophenyl)pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 86. MS (ESI): mass calcd. for Ci ₉ Hi ₈ FN ₃ 0, 323.1 ; m/z found, 324.2 [M+H] ⁺ . Ή HMR (500 MHz, DMSO-cfe) δ 8.65 - 8.62 (m, 1 H), 8.31 (t, J = 5.8 Hz, 1 H), 8.08 (s, 1 H), 7.81 - 7.74 (m, 2H), 7.66 - 7.63 (m, 1 H), 7.37 - 7.30 (m, 2H), 6.61 - 6.58 (m, 1 H), 4.93 (s, 2H), 3.00 - 2.95 (m, 2H), 0.95 - 0.86 (m, 1 H), 0.42 - 0.36 (m, 2H), 0.17 - 0.12 (m, 2H).

Example 238: 6-(4-Fluoro-3-methyl-phenyl)-1 -id -methyltriazol-4- yl)methyl]pyrrolo 3,2-b]pyridine.

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine and 4- (chloromethyl)-1 -methyl-1 H-1 ,2,3-triazole. MS (ESI): mass calcd. for

Ci ₈ Hi ₆ FN ₅ , 321 .1 ; m/z found, 322.2 [ +Hf. H NMR (400 MHz, DMSO-efe) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.29 - 8.26 (m, 1 H), 8.01 (s, 1 H), 7.75 (d, J = 3.3 Hz, 1 H), 7.72 - 7.67 (m, 1 H), 7.63 - 7.57 (m, 1 H), 7.27 (dd, J = 9.7, 8.5 Hz, 1 H), 6.59 (dd, J = 3.2, 0.9 Hz, 1 H), 5.56 (s, 2H), 3.97 (s, 3H), 2.34 (d, J = 1 .9 Hz, 3H). Example 239: 5-ii3-Chioro-6-(4-fluoro-3-niethvi-phenyl)pyrroloi3,2-blpyri din-

The title compound was prepared in a manner analogous to Example 176. M! (ESI): mass calcd. for C18H14CIFN4O, 356.1 ; m/z found, 357.1 [M+H] ⁺ . Ή N R (400 MHz, DMSO-d ₆ ) δ 8.77 (d, J = 1 .8 Hz, 1 H), 8.39 (d, J = 2.0 Hz, 1 H), 8.00 (s, 1 H), 7.73 - 7.69 (m, 1 H), 7.64 - 7.57 (m, 1 H), 7.28 (dd, J = 9.7, 8.5 Hz, 1 H), 5.96 (s, 2H), 2.33 (d, J = 1 .9 Hz, 3H), 2.26 (s, 3H). Example 240: 3-Chloro-6-(4-fluoro-3-methy ienyl)-1 -id -methylpyrazol-4-

The title compound was prepared in a manner analogous to Example 176. MS (ES!): mass calcd. for Ci ₉ H ₆ CIFN _4l 354.1 ; m/z found, 355.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.69 (d, J = 1 .9 Hz, 1 H), 8.31 (d, J = 2.0 Hz, 1 H), 7.91 (s, 1 H), 7.72 - 7,68 (m, 1 H), 7.63 - 7.57 (m, 2H), 7.28 (t, J = 9.7, 8,5 Hz, 1 H), 6.19 (d, J = 2.2 Hz, 1 H), 5.41 (s, 2H), 3.77 (s, 3H), 2.34 (d, J = 2.0 Hz, 3H). -i3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrroloi3.2-b]pyridin -1 -

The title compound was prepared in a manner analogous to Example 176, MS (ES!): mass calcd. for C ₂ oHi ₈ CiFN ₂ 0, 356.1 ; m/z found, 357.1 [M+H] ⁺ .

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C). R _t = 1 .28 min at 254 nm. -Cyclobutyl-2-[6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 170 using 6~(4-fluoro-3~methyiphenyl)~1 H~pyrrolo[3,2-b]pyridine and 2-bromo-1 - cyclobutylethanone. MS (ESI): mass calcd. for C20H19FN2O, 322.1 ; m/z found, 323.2 [M+H] ⁺ Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C). Rt = 0.99 min at 254 nm.

Example 2^ -6-f5~(trifluoromethyl)-3~

Pyridvnpyrrolo[3,2-blpyridin-1 -yilefhanone trifluoroacetate sal

Step A: 3-ChiQro-6-(5-(trifluoromethyi)pyridin-3-yl)-1 H-pyrroiQ[3,2-blpyridine.

The title compound was prepared in a manner analogous to Example 27 _: Step A, substituting (5-(trifluoromethyl)pyridin-3-yl)boronic acid for (4- fluorophenyl)boronic acid, ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 1 1 .87 (s, 1 H) _; ((dd,, JJ == 22,,22 HHzz,, 11 HH)),, 99,,0011 -- 88,,9977 ((mm,, 11 HH)),, 88..8844 ((dd,, JJ == 22..00 HHzz,, 11 HH)),, 88..6600 -- 88..5566 ((mm,, 11 HH)),, 88..2266 ((dd,, JJ == 22..00 HHzz,, 11 HH)),, 77..9955 ((ss,, 11 HH))..

SStteepp BB:: 11 --((AAzzeettiiddiinn--11 --vynl)--22--ii33--cchhiloorroo--86--ii55--((ttrriifflluuoor roormneetthhvynn--33--ppyyrriiddvynnppyyrrrroolloo[[33,,22-- bbllppyyrriiddiinn--11 --yylllleetthhaannoonnee ttrriifflluuoorrooaacceettaattee ssaalltt.. TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 6688,, sstteepp BB.. MMSS ((EESSII)):: mmaassss ccaallccdd,, ffoorr CC ₁₁₈₈ HHii ₄₄ CCI!FF ₃₃ NN ₄₄ O0,, 339944..11 ;; mm//zz ffoouunndd,, 339955..11 [[MM++HH]f ⁺ .. HH IIMMMMRR ( (440000 MMHHzz,, DDMMSSOO-- ccfefe)) δδ 99,,3333 ((ss,, 11 HH)),, 99,,0011 ((ss,, 11 HH)),, 88..9900 ((dd,, JJ == 11 ..99 HHzz,, 11 HH)),, 88..5599 ((tt,, JJ == 22..22 HHzz,, 11 HH)),, 88..4488 ((dd,, JJ == 11 ..99 HHzz,, 11 HH)),, 77..8888 ((ss,, 11 HH)),, 55..0044 ((ss,, 22HH)),, 44..2255 ((tt,, JJ == 77,,77 HHzz,, 22HH)),, 33..9911 ((tt,, JJ == 77..77 HHzz,, 22HH)),, 22..3344 -- 22..2255 ((mm,, 22HH))..

EExxaammppllee 224444:: 22--ff33--CChhlloorroo--66--ff55--((ttrriifflluuoorroommeett hhvyll))--33--ppyyrriiddyyllllppyyrrrroolloo[[33,,22--bbllpp yyrriiddiinn--

The title compound was prepared in a manner analogous to Example 243. MS (ESI): mass calcd. for Ci8Hi ₄ CiF ₃ N ₄ 0, 394,1 ; m/z found, 395, 1 [M+Hf. H IMMR (400 MHz, DMSO-cfe) δ 9.33 (s, 1 H), 9.01 (s, 1 H), 8.92 (d, J = 1 .9 Hz, 1 H), 8.61 - 8.57 (m, 1 H), 8.49 (d, J = 1 .9 Hz, 1 H), 8.34 (d, J = 4.2 Hz, 1 H), 7.94 (s, 1 H), 4.93 (s, 2H), 2.69 - 2.61 (m, 1 H), 0.67 - 0.60 (m, 2H), 0.49 - 0.41 (m, 2H). -(Azetidin-1 -yl)-2-[3-chloro-6-r6-(trifluoromethyl)-2-

The title compound was prepared in a manner analogous to Example 243, substituting 2-(4,4,5,5~tetramethyi~1 ,3,2~dioxaborolan~2-yi)~6- (trifluoromethyl)pyridine for (5-(trifluoromethyl)pyridin-3-yl)boronic acid, MS (ESI): mass calcd. for 394.1 ; m/z found, 395.1 [M+H] ⁺ H NMR (400 MHz, DMSO-d ₆ ) δ 9.17 (d, J = 1 .8 Hz, 1 H), 8.59 (d, J = 1 .8 Hz, 1 H), 8.40 (d, J = 8.1 Hz, 1 H), 8,24 (t, J = 7.9 Hz, 1 H), 7.90 (s, 2H), 5.07 (s, 2H), 4.28 (t, J = 7.7 Hz, 2H), 3.92 (t, J = 7.7 Hz, 2H), 2.35 - 2.25 (m, 2H).

Example 246: 2-r3-Chloro-6-f6-(trifluoromethyl)-2-pyridyllpyrrolo[3.2-blp yridin-

1 -yl]-N-cyclopropyl-acetamide.

The title compound was prepared in a manner analogous to Example 243 substituting 2-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-6- (trifluoromethyl)pyridine for (5-(trifiuoromethyl)pyridin-3~yi)boronic acid. MS (ESI): mass calcd. for 394.1 ; m/z found, 395, 1 [M+Hf. H NMR (400 MHz, DMSO-cfe) δ 9.18 (d, J = 1 .8 Hz, 1 H), 8.55 (d, J = 1 .9 Hz, 1 H), 8.44 - 8.39 (m, 2H), 8.23 (t, J = 7.9 Hz, 1 H), 7.95 (s, 1 H), 7.89 (d, J = 7 Hz, 1 H), 4.93 (s, 2H), 2.69 - 2,61 (m, 1 H), 0,67 - 0.60 (m, 2H), 0.49 - 0.43 (m, 2H).

EExxaammppllee 224477:: 22--[[33--CChhlloorroo--66--ff66--((ttrriifflluuoorroommeett hhvyll))--22--ppyyrriiddvyllllppyyrrrroollooff33,,22--bb]]pp yyrriiddiinn--

The title compound was prepared in a manner analogous to Example 243 substituting 2-(4,4 _! 5,5~tetramethyi~1 ,3,2~dioxaborolan~2-yi)~6- (trifluoromeihyl)pyridine for (5-(trifluoromethyl)pyridin-3-yl)boronic acid, MS (ESI): mass calcd. for CieHi3CIF ₄ N ₄ 0, 412.1 ; m/z found, 413.1 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) δ 9.16 (d, J = 1 .8 Hz, 1 H), 8.60 (d, J = 1 .8 Hz, 1 H), 8.25 (d, J = 8.0 Hz, 1 H), 8.12 (t, J = 7.9 Hz, 1 H), 7.76 (d, J = 7,7 Hz, 1 H), 7,71 (s, 1 H), 5.54 - 5.32 (m, 1 H), 5.1 1 (s, 2H), 4.70 - 4.56 (m, 1 H), 4.51 - 4.27 (m, 2H), 4.19 - 4.04 (m, 1 H).

Example 248: N-Cvclopropyl-2-i6-(3,4.5-trifluorophenyl)pyrroloi3.2-blpyri din- 1 -yllacetamide.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N-cyclopropylacetamide (intermediate of Step A, Example 75) and (3,4,5~trifiuorophenyi)boronic acid. MS (ESI): mass calcd. for C 8H14F3N3G, 345.1 ; m/z found, 346.1 [M+H] ⁺ . Ή NMR (400 MHz, DMSO-d ₆ ) δ 8.73 (d, J = 2.0 Hz, 1 H), 8.32 (d, J = 4.3 Hz, 1 H), 8.23 - 8.20 (m, 1 H), 7.84 - 7.76 (m, 2H), 7.68 (d, J = 3.3 Hz, 1 H), 6.61 (dd, J = 3.2, 0.9 Hz, 1 H), 4.88 (s, 2H), 2.69 - 2.61 (m, 1 H), 0.67 - 0.60 (m, 2H), 0.47 - 0.41 (m, 2H).

Example 249: N-Cvclopropyl-2-[6-(2,3,4-trifluorophenyl)pyrroloi3,2-blpyri din

1 -yi]acetamide.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N-cyclopropylacetamide (intermediate of Step A, Example 75) and (2,3,4-trifluorophenyl)boronic acid. MS (ESI): mass calcd. for C 8H14F3N3O, 345.1 ; m/z found, 346.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-cfe) δ 8.50 (t, J = 2.0 Hz, 1 H), 8.34 (d, J = 4.1 Hz, 1 H), 8.01 - 7.98 (m, 1 H), 7.70 (d, J = 3.3 Hz, 1 H), 7.51 - 7.45 (m, 2H), 6.63 (dd, J = 3.2, 0.9 Hz, 1 H), 4.86 (s, 2H), 2.67 - 2.60 (m, 1 H), 0.63 (td, J = 7.0, 4.7 Hz, 2H), 0.46 - 0.40 (m, 2H).

Example 250: N-Cvclopropyl-2-f6-[3-(difluoromethyl)phenvnpyrrolof3,2- b]pyridin-1 -yllacetamide.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo~1 H~pyrrolo[3,2-b]pyridin-1 ~yi)-N~cyciopropyiacetamide (intermediate of Step A, Example 75) and (3-(difluoromethyl)phenyl)boronic acid. MS (ESI): mass calcd. for G19H17F2N3O, 341.1 ; m/z found, 342.1 [M+H] ⁺ H NMR (400 MHz, DMSO-de) δ 8.69 (d, J = 2.0 Hz, 1 H), 8.35 (d, J = 4.2 Hz, 1 H), 8.15 - 8.13 (m, 1 H), 7.95 - 7.90 (m, 2H), 7.69 - 7.63 (m, 2H), 7.61 - 7.56 (m, 1 H), 7.12 (t, J = 55.8 Hz, 1 H), 6.61 (dd, J = 3.3, 0.8 Hz, 1 H), 4.89 (s, 2H), 2.70 - 2.61 (m, 1 H), 0.66 - 0.60 (m, 2H), 0.47 - 0.42 (m, 2H).

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C22H18FN3O, 359.1 ; m/z found, 360.2 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-cfe) δ 8,70 (t, J = 5.9 Hz, 1 H), 8.64 (d, J = 2.0 Hz, 1 H), 8.07 (dd, J = 2.0, 0.9 Hz, 1 H), 7.77 - 7.71 (m, 2H), 7.68 (d, J = 3,2 Hz, 1 H), 7.37 -

7.30 (m, 2H), 7.28 - 7.19 (m, 5H), 6.60 (dd, J = 3.2, 0.9 Hz, 1 H), 5.01 (s, 2H),

4.31 (d, J = 5.9 Hz, 2H). Example 252: 2-[[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-blpyridin-1 - yllmethynoxazole.

The title compound was prepared in a manner analogous to Example 170 using 6-(4~fluoro~3-methylphenyl)-1 H-pyrrolo[3,2~b]pyridine and 2- (chloromethyl)oxazole. MS (ESI): mass calcd. for C18H14FN3O, 307, 1 ; m/z found, 308.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 2.0 Hz, 1 H), 8.21 (dd, J = 2.1 , 0.9 Hz, 1 H), 8.06 (d, J = 1 .0 Hz, 1 H), 7.77 (d, J = 3.3 Hz, 1 H), 7.69 - 7.65 (m, 1 H), 7.60 - 7.54 (m, 1 H), 7.26 (dd, J = 9.7, 8.5 Hz, 1 H), 7.17 (d, J = 0.9 Hz, 1 H), 6.64 (dd, J = 3.3, 0.9 Hz, 1 H), 5.74 (s, 2H), 2.33 (d, J = 1 .9 Hz, 3H).

Example 253: 2-f6-(4-Fluorophenyl)pyrrolor3,2-blpyridin-1 -νΠ-Ν-(2- hydroxyethvDacetam ide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for Ci ₇ H ₁₆ FN ₃ 0 _2l 313.1 ; m/z found, 314.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.64 (d, J = 2.0 Hz, 1 H), 8.25 - 8.20 (m, 1 H), 8.12 - 8.09 (m, 1 H), 7.81 - 7.76 (m, 2H), 7.66 (d, J = 3.3 Hz, 1 H), 7.37 - 7.30 (m, 2H), 6.60 (dd, J = 3.2, 0.9 Hz, 1 H), 4.94 (s, 2H), 4.74 - 4.70 (m, 1 H), 3.46 - 3.40 (m, 2H), 3.19 - 3.13 (m, 2H). -[6-(4-Fluorophenyl)pyrrolof3,2-blpyridin-1 -yl1-N-(2-

The title compound was prepared in a manner analogous to Example 88. MS (ESI): mass calcd. for Ci ₈ Hi ₈ FN ₃ G2, 327.1 ; m/z found, 328.2 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.64 (d, J = 2.0 Hz, 1 H), 8.32 (t, J = 5.5 Hz, 1 H), 8.09 - 8.07 (m, 1 H), 7.81 - 7.74 (m, 2H), 7.65 (d, J = 3.3 Hz, 1 H), 7.37 - 7.30 (m, 2H), 6.59 (dd, J = 3.4, 0.8 Hz, 1 H), 4.94 (s, 2H), 3.38 - 3.31 (m, 2H), 3.28 - 3.23 (m, 2H), 3.21 (s, 3H).

Example 255: 1 -(3,3-Difluoroazetidin-1 -vn-2-f6-r2-fluoro-3-

(trifluoromethyl)phenyl]pyrrolQ[3,2-b]pyridin-1 -yl]ethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 106. MS (ESI): mass calcd. for C19H13F6N3O, 413.1 ; m/z found, 414.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-ds) δ 8.82 (s, 1 H), 8.63 (s, 1 H), 8.04 - 7.98 (m, 2H), 7.92 (t, J = 8.8 Hz, 1 H), 7.62 (t, J = 7.8 Hz, 1 H), 6.85 (d, J = 3.4 Hz, 1 H), 5.29 (s, 2H), 4.76 (t, J = 12.3 Hz, 2H), 4.38 (t, J = 12.5 Hz, 2H). -(3,3-Difluoroazetidin-1 -yl)-2-r6-(3-fluorophenyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 106, MS (ES!): mass calcd. for dsH ^i^G, 345.1 ; m/z found, 346.1 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 9.01 - 8.93 (m, 2H), 8.09 (d, J = 3,3 Hz, 1 H), 7.68 - 7.57 (m, 3H), 7.30 - 7.23 (m, 1 H), 6,94 (dd, J = 3.3, 1 .0 Hz, 1 H), 5.38 (s, 2H), 4.84 - 4.77 (m, 2H), 4.50 - 4.39 (m, 2H). Example 257: 1 -(3,3-Difluoroazetidin-1 -yl)-2-(6-phenylpyrrolo[3,2-blpyridin-1

The title compound was prepared in a manner analogous to Example 106. MS (ESI): mass calcd. for Ci ₈ H ₁₅ F2N ₃ 0, 327.1 ; m/z found, 328.1 [M+H] ⁺ . ¹ H NMR (400 MHz, CD3OD) δ 8.97 (s, 1 H), 8.91 (s, 1 H), 8.07 (d, J = 3.3 Hz, 1 H), 7.85 - 7.79 (m, 2H), 7.62 - 7.55 (m, 2H), 7.54 - 7.49 (m, 1 H), 6.94 (d, J = 3.3 Hz, 1 H), 5.38 (s, 2H), 4.81 (t, J = 1 1 .9 Hz, 2H), 4.45 (t, J = 12.1 Hz, 2H).

-(3,3-Difluoroazetidin-1 -yl)-2-f6-(3-ethylphenyl)pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 106. S (ESI): mass calcd. for C20H19F2N3O, 355.1 ; m/z found, 356.2 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.96 - 8.94 (m, 1 H), 8.90 (d, J = 1 .5 Hz, 1 H), 8.06 (d, J = 3.4 Hz, 1 H), 7.67 - 7.65 (m, 1 H), 7.63 - 7.58 (m, 1 H), 7.49 (t, J = 7.7 Hz, 1 H), 7.39 - 7.35 (m, 1 H), 6,93 (dd, J = 3.3, 0.8 Hz, 1 H), 5.39 (s, 2H), 4.81 (t, J = 12.0 Hz, 2H), 4.45 (t, J = 12.1 Hz, 2H), 2.78 (q, J = 7.6 Hz, 2H), 1 .32 (t, J = 7.6 Hz, 3H).

Example 259: 1 -(3,3-Difluoroazetidin-1 -yl)-2-f6-(4-fluoro-3-methyl- phenyl spyrrolQi3,2-blpyridin-1 -yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 106. MS (ESI): mass calcd. for Ci ₉ H ₁₆ F3 ₃ 0, 359.1 ; m/z found, 360.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.99 (s, 1 H), 8.87 (s, 1 H), 8.06 (d, J = 3.2 Hz, 1 H), 7.79 (dd, J = 7.3, 2.4 Hz, 1 H), 7.73 - 7.67 (m, 1 H), 7.41 - 7.34 (m, 1 H), 6.87 (d, J = 3,3 Hz, 1 H), 5,35 (s, 2H), 4.79 (t, J = 12,4 Hz, 2H), 4.39 (t, J = 12,5 Hz, 2H), 2.36 (d, J = 1 .9 Hz, 3H). -(3,3-Difluoroazetidin-1-yl)-2-f6-f3-

The title compound was prepared in a manner analogous to Example 106. S (ESI): massca!cd. for Ci9Hi ₄ F ₅ N ₃ 0, 395,1; m/z found, 396,1 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD)58,97 (s, 2H), 8,15 (s, 1H), 8.10-8.09 (m, 1H), 8.08 (d, J = 3.4 Hz, 1 H), 7.85 - 7.76 (m, 2H), 6.94 (d, J = 3,3 Hz, 1 H), 5,38 (s, 2H), 4,80 (t, J= 11.8 Hz, 2H), 4,45 (t, J = 12,1 Hz, 2H). Example 261 : 1 -(3,3-Difluoroazetidin-1 -yl)-2-r6-(4-fluoro-2-methyl- phenyl)pyrrolof3,2-blpyridin-1 -yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 106. MS (ESI): mass calcd. for C19H16F3N3O, 359,1; m/z found, 360,2 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.68 - 8.65 (m, 1 H), 8.63 - 8.60 (m, 1 H), 8.09 (d, J = 3.4 Hz, 1H), 7.39 (dd, J = 8.5, 5.8 Hz, 1H), 7.17 (dd, J= 9.8, 2.7 Hz, 1H), 7.13 - 7.07 (m, 1 H), 6.96 (dd, J = 3.4, 1.0 Hz, 1 H), 5.33 (s, 2H), 4.77 (t, J = 11.9 Hz, 2H), 4.42 (t, J = 12.1 Hz, 2H), 2.31 (s, 3H). -(3-Fluoroazetidin-1 -yl)-2-[6-i4-fiuoro-3-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3-fluoroazetidin-1 - yl)ethanone (Intermediate 13) and (4-fiuoro-3~(trifiuoromethyi)phenyi)boronic acid. MS (ESI): mass calcd. for C19H14F5N3O, 395.1 ; m/z found, 396.0 [M+H] ⁺ . Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsii ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 niL/min (Temperature = 50 °C). F¾ = 0.93 min at 254 nm.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3 _! 2-b]pyridin-1 -yl)-1 -(3-fiuoroazefidin-1 - yl)ethanone (Intermediate 13) and (4-fiuorophenyl)boronic acid. MS (ESI): mass calcd. for 327.1 ; m/z found, 328.0 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.96 - 8.91 (m, 2H), 8.08 (d, J = 3.4 Hz, 1 H), 7.69 - 7.56 (m, 3H), 7.29 - 7.21 (m, 1 H), 6.93 (dd, J = 3.4, 0.9 Hz, 1 H), 5.57 - 5.37 (m, 1 H), 5.32 (d, J = 3.5 Hz, 2H), 4.78 - 4.64 (m, 1 H), 4.56 - 4.44 (m, 1 H), 4.44 - 4.32 (m, 1 H), 4.20 - 4.07 (m, 1 H). -(3-Fluoroazetidin-1-yl)-2-r6-(4-fluoro-2-methv

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1H-pyrrolo[3,2-b]pyridin-1-yl)-1-(3-fluoroazetidi n-1- yl)ethanone (Intermediate 13) and (4-fluoro-2-methylphenyl)boronic acid. MS (ESI): masscalcd. for C19H17F2N3O, 341.1; m/z found, 342.1 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.65 (t, J = 1.2 Hz, 1 H), 8.61 (d, J = 1.5 Hz, 1 H), 8.09 (d, J= 3.3 Hz, 1H), 7.39 (dd, J = 8.5, 5.7 Hz, 1H), 7.17 (dd, J = 9.8, 2.7 Hz, 1H), 7.13- 7.06 (m, 1 H), 6.95 (dd, J = 3.4, 0.9 Hz, 1H), 5.54 - 5.34 (m, 1H), 5,28 (d, J = 4.2 Hz, 2H), 4.74 - 4.62 (m, 1 H), 4.53 - 4.41 (m, 1 H), 4.41 - 4.30 (m, 1H), 4.17-4.05 (m, 1H), 2.32 (s, 3H).

Example 265: 1-(3-Fluoroazetidin-1-yl)-2-[6-[3- (trifluoromethyl)phenyllpyrrolof3,2-blpyridin-1 -yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yi)-1 -(3-fluoroazetidin-1 - yi)ethanone (Intermediate 13) and (3-(trifluoromethyl)phenyl)boronic acid. MS (ESI): mass calcd. for 377.1; m/z found, 378.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 9.04 (s, 1H), 8.85 (s, 1H), 8.21 - 8.12 (m, 2H), 8.03 (d, J = 3.4 Hz, 1 H), 7.88 - 7.79 (m, 2H), 6.85 (d, J = 3.3 Hz, 1 H), 5.58 - 5.41 (m, 1 H), 5.27 (s, 2H), 4.67 - 4.56 (m, 1 H), 4.43 - 4.32 (m, 1 H), 4.31 - 4.21 (m, 1H), 4,04-3,93 (m, 1H).

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2~(6~bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3-fluoroazetidin-1 - yl)ethanone (Intermediate 13) and m-toiyiboronic acid, MS (ESI): mass calcd. for CigHisFNaO, 323.1 ; m/z found, 324.1 [M+H] ^{+ 1} H N MR (400 MHz, DMSO- cfe) δ 9.00 (d, J = 1 .6 Hz, 1 H), 8.93 - 8.91 (m, 1 H), 8.08 (d, J = 3.3 Hz, 1 H), 7.68 (s, 1 H), 7.67 - 7.63 (m, 1 H), 7,51 - 7,44 (m, 1 H), 7.35 - 7.28 (m, 1 H), 6.89 - 6.86 (m, 1 H), 5.61 - 5.40 (m, 1 H), 5.30 (s, 2H), 4.70 - 4.56 (m, 1 H), 4.46 - 4.33 (m, 1 H), 4.32 - 4.20 (m, 1 H), 4.07 - 3.92 (m, 1 H), 2,44 (s, 3H),

Example 267: 1 -(3-Fluoroazetidin-1 -yl)-2-r6-f2-fluoro-3- (trifluoromethyl)phenyllpyrrolof3,2-blpyridin-1 -yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3-f!uoroazetidin-1 - yi)ethanone (Intermediate 13) and (2-fluoro-3-(trifluoromethyl)phenyl)boronic acid. MS (ESI): mass calcd, for C 19H14F5N3O, 395.1 ; m/z found, 396.2 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-d ₆ ) δ 8.77 (s, 1 H), 8.54 (s, 1 H), 8.04 - 7.97 (m, 1 H), 7.95 (d, J = 3.2 Hz, 1 H), 7.93 - 7.87 (m, 1 H), 7.61 (t, J = 7.8 Hz, 1 H), 6.81 (d, J = 3.3 Hz, 1 H), 5.59 - 5,37 (m, 1 H), 5,20 (d, J = 2.6 Hz, 2H), 4.66 - 4.52 (m, 1 H), 4.42 - 4.30 (m, 1 H), 4.30 - 4.18 (m, 1 H), 4.03 - 3.91 (m, 1 H).

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2~(6~bromo-1 H-pyrrolo[3,2~bjjpyridin~1 -yl)-1 -(3-fluoroazetidin-1 - yl)ethanone (Intermediate 13) and (3-ethyiphenyl)boronic acid, MS (ESI): mass calcd. for C ₂ oH ₂ oFN ₃ 0, 337.2; m/z found, 338.1 [M+H] ⁺ . ¹ H IMMR (400 MHz, DMSO-de) δ 8.96 (d, J = 1 .7 Hz, 1 H), 8.80 (s, 1 H), 8.02 (d, J = 3.3 Hz, 1 H), 7.72 - 7.61 (m, 2H), 7.49 (t, J = 7.6 Hz, 1 H), 7.34 (d, J = 7.7 Hz, 1 H), 6.84 (d, J = 3.2 Hz, 1 H), 5.61 - 5.39 (m, 1 H), 5.27 (d, J = 1 .9 Hz, 2H), 4.68 - 4.54 (m, 1 H), 4.47 - 4.32 (m, 1 H), 4.33 - 4.20 (m, 1 H), 4.04 - 3,91 (m, 1 H), 2.73 (q, J = 7.6 Hz, 2H), 1 .27 (t, J = 7.6 Hz, 3H). -(3,3-Difluoroazetidin-1 -yl)-2-[6-(m-tolyl)pyrrolo[3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-brorno-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3,3-difluoroazetidin-1 - yl)ethanone (Intermediate 12) and m-tolylboronic acid. MS (ESI): mass calcd. for Ci ₉ Hi ₇ F2N ₃ 0 _! 341 .1 ; m/z found, 342.1 [Mn-H] ^÷ . Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1.6 min and then hold at 99% ACN for 0.4 rn n, at a flow rate of 2.2 mL/min (Temperature = 50 °C). Rt = 0.88 min at 254 nm.

Example 270: 1 -(3-Fluoroazetidin-1 -yl)-2-(6-phenylpyrrolof3,2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo~1 H~pyrrolo[3 _! 2-b]pyridin-1 ~yi)-1 ~(3~fluoroazetidin~1 - yl)ethanone (Intermediate 13) and phenyl boronic acid. MS (ESI): mass calcd. for dsH ieFNsO, 309.1 ; m/z found, 310.1 [M+H] ⁺ . -(3,3-Difluoroazetidin-1 -yl)-2-f6-(2,4-difluoro-3-methyl-

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3,3- difiuoroazetidin-1 -yi)ethanone (Intermediate 16) and (2,4-difluoro-3- methylphenyl)boronic acid. MS (ESI): mass calcd. for C19H14F5N3O, 395.1 ; m/z found, 396.0 [M+H] ⁺ H IMMR (500 MHz, DMSO~cf ₆ ) δ 8.52 - 8.47 (m, 1 H), 8.08 (s, 1 H), 7.68 (d, J = 2.1 Hz, 1 H), 7.50 - 7.42 (m, 1 H), 7.27 - 7.18 (m, 1 H), 5.07 (s, 2H), 4.72 (t, J = 12.3 Hz, 2H), 4.42 - 4.30 (m, 2H), 2.25 (s, 3H). Example 272: (R/SV1 -r6-(3,5-Difluorophenyl)pyrrolof3,2-blpyridin-1 -yll-3-

To a solution of compound of 1 -[6-(3,5-difluorophenyl)pyrrolo[3,2-b]pyridin-1 - yl]-3-methy!-butan-2-one (Example 364, 60 mg, 0.19 mmoi) in a mixture of THF (2.5 mL) and MeOH (2.5 mL) cooled at 0 °C was added IMaBH ₄ (14 mg, 0.38 mmol). The reaction mixture was stirred at 0 °C for 30 minutes. The volatiles were evaporated and the residue was taken up in EtOAc and water. The aqueous phase was extracted 2 times with EtOAc. The combined organic layers were washed with water, dried (MgSO ), filtered and evaporated to afford the title compound (39 mg, 64%). MS (ES!): mass calcd. for

316.1 ; m/z found, 317.1 [M+H] ⁺ . Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C). ί¾ = 0.93 min at 254 nm.

Example 273: 246- hvdroxyazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for α ₁₉ Η ₁₈ ΡΝ ₃ Ο ₂ , 339.1 ; m/z found, 340.1 [M+H] ⁺ . H NMR (500 MHz, CDCI ₃ ) δ 8.61 (d, J = 1 .9 Hz, 1 H), 7.70 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.42 - 7.38 (m, 1 H), 7.39 - 7.34 (m, 1 H), 7.28 (d, J = 3.3 Hz, 1 H), 7.08 (t, J = 8.9 Hz, 1 H), 6.70 (dd, J = 3.3, 0.9 Hz, 1 H), 4.76 (s, 2H), 4.59 - 4.53 (m, 4.28 - 4.20 (m, 1 H), 3.94 - 3,85 (m, 2H), 3.69 - 3.64 (m, 1 H), 2.35 (d, J = 1 .9 Hz, 3H), 2.16 (br. s, 1 H).

Example 274: (R/S)-1 -Cyctopropyl-2-i6-(4-fluorQ-3-methyl-phenyl)pyrroloi3,2- b]pyridin-1 -yilethanol.

The title compound was prepared in a manner analogous to Example 272. MS (ES!): mass calcd. for Ci ₉ Hi ₉ FN ₂ 0, 310.1 ; m/z found, 31 1 .1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.59 (d, J = 2.0 Hz, 1 H), 8.13 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.71 - 7.65 (m, 2H), 7.62 - 7.55 (m, 1 H), 7.29 - 7.22 (m, 1 H), 6.55 (dd, J = 3.2, 0.9 Hz, 1 H), 4.92 (d, J = 5.0 Hz, 1 H), 4.33 (dd, J = 14.2, 4.3 Hz, 1 H), 4.24 (dd, J = 14.3, 7.1 Hz, 1 H), 3.29 - 3.24 (m, 1 H), 2.33 (d, J = 1 .9 Hz, 3H), 0.84 - 0.75 (m, 1 H), 0.37 - 0.22 (m, 3H), 0.18 - 0.1 1 (m, 1 H). Example 275: (R/S)-2-Cyclopropyl-1 -[6-(4-fluoro-3-methyl-phenyl)pyrrolor3,2- blpyridin-1 -yllpropan-2-ol trifluoroacetate salt.

To a solution of compound of 1 -cyclopropyl-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone (Example 186, 35 mg, 0.1 1 mmol) in THF (4 ml_) cooled at 0 °C was slowly added a solution of 3M CH ₃ MgBr in

Et ₂ 0 (1 14 μΙ_, 0.34 mmol). The reaction mixture was stirred at 0 °C for 3 hours and water was added. The aqueous phase was extracted 2 times with EtOAc.

The combined organic layers were dried (MgS0 ₄ ), filtered and evaporated.

Purification by HPLC Method C gave the title compound (4 mg, 8%). MS (ESI): mass calcd. for C ₂ oH ₂ i FN ₂ 0, 324.2; m/z found, 325.1 [M+H] ⁺ . ¹ H NMR

(400 MHz, DMSO-C/B) Π8.90 (s, 2H), 8.08 - 8.02 (m, 1 H), 7.81 - 7.75 (m, 1 H), 7.73 - 7.66 (m, 1 H), 7.35 (t, 7= 9.1 Hz, 1 H), 6.79 (d, 7= 3.3 Hz, 1 H), 4.44 (s, 2H), 2.35 (s, 3H), 1 .09 (s, 3H), 0.94 - 0.84 (m, 1 H), 0.29 - 0.14 (m, 2H), 0.06 - -0.09 (m, 2H). Example 276: 1 -Cvclopropyl-2-f6-(4-fluoro-3-methyl-phenyl)pyrrolof3,2-

To a solution of compound of 1 -cyc!opropyi-2-[6-(4~fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone (Example 186, 35 mg, 0.1 1 mmol) in EtOH (5.7 ml_) was added O-methylhydroxylamine hydrochloride (19 mg, 0.23 mmol). The reaction mixture was stirred at room temperature for 10 minutes and NaHC0 ₃ (19 mg, 0.23 mmol) was added. After 2 hours, water was added and the aqueous phase was extracted with EtOAc. The organic phase was then dried over MgS0 ₄ , filtered and evaporated. Purification (FCC, SiO ₂ ,0-100% EtOAc in hexanes) gave the title compound (6 mg, 15%). MS (ESI): mass calcd. for C ₂ oH ₂ oFfM ₃ 0, 337.2; m/z found, 338.1 [M+H] ⁺ . ¹ H HMR (500 MHz, DMSO-cfe) δ 8,66 (d, J = 2.0 Hz, 1 H), 8.15 - 8.1 1 (m, 1 H), 7.73 (d, J = 3.3 Hz, 1 H), 7.71 - 7.68 (m, 1 H), 7.63 - 7.58 (m, 1 H), 7,30 - 7.22 (m, 1 H), 6.65 (dd, J = 3.3, 0.9 Hz, 1 H), 5.24 (s, 2H), 3.84 (s, 3H), 2.33 (d, J = 1 .9 Hz, 3H), 0.88 - 0.83 (m, 1 H), 0.56 - 0.50 (m, 2H), 0.40 - 0.34 (m, 2H).

Example 277: 1 ~(3~Fluoroazetidin~1 -yl)-2-[6-(2-thienyl)pyrrolof3,2-b]pyridin-1 - yilethanone.

The title compound was prepared in a manner analogous to Example 128, MS (ES!): mass calcd. for Ci ₆ H _i4 FN ₃ OS, 315.1 ; m/z found, 316.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-ds) δ 8.67 (d, J = 1 .9 Hz, 1 H), 8.07 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.59 (d, J = 3.3 Hz, 1 H), 7.58 - 7,53 (m, 2H), 7, 18 (dd, J = 5.1 , 3,7 Hz, 1 H), 6.60 (dd, J = 3.2, 1 .0 Hz, 1 H), 5.57 - 5.36 (m, 1 H), 5.06 (d, J = 2.5 Hz, 2H), 4.61 - 4.49 (m, 1 H), 4.37 - 4.20 (m, 2H), 4.04 - 3.91 (m, 1 H),

Example 278: 1 -Pyrrolidin-1 -yl-2-i6-(2-thienyl)pyrroloi3,2-blpyridin-1 - yllethanone.

The title compound was prepared in a manner analogous to Example 105. MS (ES!): mass calcd. for Ci ₇ H _{i 7} N ₃ OS, 31 1 .1 ; m/z found, 312.0 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.61 (d, J = 1 .9 Hz, 1 H), 8.08 - 8.06 (m, 1 H), 7.54 (d, J = 3,3 Hz, 1 H), 7,47 (dd, J = 3.6, 1 .2 Hz, 1 H), 7.42 (dd, J = 5.1 , 1 .2 Hz, 1 H), 7.13 (dd, J = 5.1 , 3.6 Hz, 1 H), 6.64 (dd, J = 3.4, 0.9 Hz, 1 H), 5.18 (s, 2H), 3.66 (t, J = 6.8 Hz, 2H), 3.47 (t, J = 6,9 Hz, 2H), 2.13 - 2.04 (m, 2H), 1 .98 - 1 .89 (m, 2H).

Example 279: 1 -(3,3-Difluoroazetidin-1 -yl)-2 6-(5-methyl-2- thienyl)pyrrolo[3,2-blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 106 substituting 4,4,5,5-tetramethyl-2-(5-methylthiophen-2-yl)-1 ,3,2-dioxaborolane for (4-fluoro~3-(trifluoromethyi)phenyi)boronic acid. MS (ES!): mass calcd. for C ₁₇ H ₁₅ F ₂ N ₃ OS, 347.1 ; m/z found, 348.0 [M+H] ⁺ , Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (3um, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mlJmin (Temperature = 50 °C).

Example 280: 1 -(3-Fiuoroazetidin-1 -yi)~2-i8~(5-methyi~2-thieny0pyrrQiQf3,2- blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 128 substituting 4,4,5,5-tetramethyl-2-(5-methylthiophen-2-yl)-1 ,3,2-dioxaborolane for (3,4-difluorophenyl)boronic acid. MS (ESI): mass calcd. for C 7H16FN3OS, 329.1 ; m/z found, 330.0 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 8.01 - 7.97 (m, 1 H), 7,52 (d, J = 3.3 Hz, 1 H), 7.25 (d, J = 3.5 Hz, 1 H), 6.82 - 6.77 (m, 1 H), 6.64 (dd, J = 3.3, 0.9 Hz, 1 H), 5.49 - 5.28 (m, 1 H), 5.04 (d, J = 2.0 Hz, 2H), 4.58 - 4.46 (m, 1 H), 4.42 - 4.26 (m, 2H), 4.17 - 4,03 (m, 1 H), 2.52 (d, J = 1 .1 Hz, 3H).

Example 281 : 2-r6-f5-Ethyl-2-thienyl)pyrrolof3.2-blpyridin-1 -yll-1 -(3- fluoroazetidin-1 -yQethanone.

The title compound was prepared in a manner analogous to Example 128 substituting 5-ethylthiophene-2-boronic acid for (4-fluoro-3- (trifluoromethyl)phenyl)boronic acid. MS (ESI): mass calcd. for dsHisFNaOS, 343.1 ; m/z found, 344.0 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.58 (d, J = 1 .8 Hz, 1 H), 8.01 - 7.99 (m, 1 H), 7,52 (d, J = 3.3 Hz, 1 H), 7.27 (d, J = 3.7 Hz, 1 H), 6.83 (dd, J = 3.7, 1 .0 Hz, 1 H), 6.66 - 6.62 (m, 1 H), 5.48 - 5.28 (m, 1 H), 5.04 (d, J = 1 .8 Hz, 2H), 4.59 - 4.45 (m, 1 H), 4.41 - 4.26 (m, 2H), 4.1 1 (dd, J = 24.7, 1 1 .6 Hz, 1 H), 2.89 (q, J = 7.5 Hz, 2H), 1.38 - 1 .31 (m, 3H).

Example 282: 2-[6-(5-Ethyl-2-thienyl)pyrrolof3,2-blpyridin-1 -yll-1 -pyrrolidin-1 - yl-ethanone.

The title compound was prepared in a manner analogous to Example 105 substituting 5-ethyithiophene-2-boronic acid for (3,4-difluorophenyl)boronic acid. MS (ESI): mass calcd. for C19H21 N3OS, 339.1 ; m/z found, 340.1 [M+H] ⁺ H N R (400 MHz, CD ₃ OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 8.01 - 7.99 (m, 1 H), 7.52 (d, J = 3.4 Hz, 1 H), 7.26 (d, J = 3.6 Hz, 1 H), 6.85 - 6.81 (m, 1 H), 6.63 (dd, J = 3.3, 0.9 Hz, 1 H), 5.16 (s, 2H), 3.66 (t, J = 6.9 Hz, 2H), 3.47 (t, J = 6.9 Hz, 2H), 2.93 - 2.84 (m, 2H), 2.13 - 2.03 (m, 2H), 1 .97 - 1 ,89 (m, 2H), 1 .34 (t, J = 7.5 Hz, 3H). -[6-(5-Methyl-2-thienyl)pyrrolo[3,2-blpyridin-1 -yll-1 -pyrrolidin-

The title compound was prepared in a manner analogous to Example 105 substituting 4,4,5,5-tetramethyl-2-(5-methylthiophen-2-yl)-1 ,3,2-dioxaborolan for (4-fluoro-3-(trifluoromethyl)phenyi)boronic acid. ¹ H NMR (400 MHz, CD3OD) δ 8.54 (d, J = 1 .9 Hz, 1 H), 8.00 - 7.97 (m, 1 H), 7.51 (d, J = 3.4 Hz, 1 H), 7.24 (d, J = 3.5 Hz, 1 H), 6.81 - 6.77 (m, 1 H), 6.62 (dd, J = 3.3, 0.9 Hz, 1 H), 5.15 (s, 2H), 3.66 (t, J = 6.8 Hz, 2H), 3.47 (t, J = 6.9 Hz, 2H), 2.51 (s, 3H), 2.12 - 2.03 (m, 2H), 1 .99 - 1 .89 (m, 2H).

Example 284: 1 -(3,3-Difluoroazetidin-l -yl)-2-f6-(5-ethyl-2-thienyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 106. MS (ES!): mass calcd. for dsH-r^NaOS, 361 .1 ; m/z found, 362.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.02 - 7.99 (m, 1 H), 7.56 (d, J = 3.3 Hz, 1 H), 7.35 (d, J = 3,5 Hz, 1 H), 6,89 (d, J = 3.5 Hz, 1 H), 6.59 (dd, J = 3.3, 0.9 Hz, 1 H), 5.12 (s, 2H), 4.72 (t, J = 1 1 .5 Hz, 2H), 4.42 - 4.34 (m, 2H), 2.89 - 2.81 (m, 2H), 1 .28 (t, J = 7.5 Hz, 3H).

Example 285: 2-[6-(4-Chloro-2-thienyl)pyrrolo[3,2-blpyridin-1 -yll- -{3- fluoroazetidin-1 -yQethanone.

The title compound was prepared in a manner analogous to Example 128 substituting 2-(4-chlorothiophen-2-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane for (3,4-difluorophenyl)boronic acid. MS (ESI): mass calcd. for

Ci ₆ H ₁₃ CIFN ₃ OS, 349.0; m/z found, 350.0 [M+H] ⁺ . H NMR (500 MHz, CD ₃ OD) 6 8.61 (d, J = 1 .9 Hz, 1 H), 8.12 - 8.10 (m, 1 H), 7.58 (d, J = 3.4 Hz, 1 H), 7.42 (d, J = 1 .5 Hz, 1 H), 7.31 (d, J = 1 .5 Hz, 1 H), 6.67 (dd, J = 3.3, 0.9 Hz, 1 H), 5.49 - 5.32 (m, 1 H), 5.07 (d, J = 3.2 Hz, 2H), 4.62 - 4.52 (m, 1 H), 4.41 - 4.31 (m, 2H), 4,16 - 4,05 (m, 1 H).

The title compound was prepared in a manner analogous to Example 278 substituting hydroxy lam ine hydrochloride for O-methylhydroxylamine hydrochloride. !VIS (ESI): mass calcd. for C- _! 9H ₁₈ FN ₃ 0, 323.1 ; m/z found, 324.1 [M+H] ⁺ H MR (400 MHz, CD ₃ OD) δ 8.89 - 8.85 (m, 2H), 8.17 (d, J = 3.3 Hz, 1 H), 7.71 - 7.67 (m, 1 H), 7.65 - 7.58 (m, 1 H), 7.29 - 7.18 (m, 1 H), 6.91 (dd, J = 3.3, 0.9 Hz, 1 H), 5.43 (s, 2H), 2.39 (d, J = 2.1 Hz, 3H), 1 .23 - 1 .14 (m, 1 H), 0.60 - 0.47 (m, 4H).

Example 287: 2-i6-(5-Chioro-2-thienyl)pyrroloi3,2-b]pyridin-1 -νΠ-1 -pyrroiidin- -yl-ethanone.

The title compound was prepared in a manner analogous to Example 105 substituting 5-chlorothiophene-2-boronic acid for (4-fluoro-3- (trifluoromethyl)phenyl)boronic acid. MS (ESI): mass calcd. for Ci ₇ Hi ₆ CilM ₃ OS, 345.1 ; m/z found, 346.0 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) δ 8.54 (d, J = 1 .9 Hz, 1 H), 8.04 - 8.00 (m, 1 H), 7,56 (d, J = 3.3 Hz, 1 H), 7.28 (d, J = 3.9 Hz, 1 H), 7.01 (d, J = 3.9 Hz, 1 H), 6.65 (dd, J = 3.3, 0.9 Hz, 1 H), 5.17 (s, 2H), 3.66 (t, J = 6.8 Hz, 2H), 3.47 (t, J = 6.9 Hz, 2H), 2.13 - 2.03 (m, 2H), 1 .98 - 1 .88 (m, 2H). -[6-(4-Chioro-2-thienyl)pyrroloi3,2-b]pyridin-1 -yll-1 -pyrrolidin-

The title compound was prepared in a manner analogous to Example 105 substituting 2-(4-cbiorothiophen-2-yi)-4,4,5 _i 5-tetramethyl-1 ,3,2-dioxaborolane for (4-fluoro~3-(trifluoromethyl)phenyl)boronic acid. MS (ES!): mass calcd. for CiyHieCINsOS, 345.1; m/z found, 346.0 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) 58.59 (d, J = 1.9 Hz, 1H), 8.10 (s, 1H), 7.58 (d, J = 3.4 Hz, 1H), 7.40 (s, 1H), 7.30 (s, 1H), 6.66 (d, J= 3.4 Hz, 1H), 5.18 (s, 2H), 3.67 (t, J = 6.8 Hz, 2H), 3.47 (t, J = 6.9 Hz, 2H), 2.13 -2.04 (m, 2H), 1 ,98 - 1 ,89 (m, 2H).

Example 289: (R/S)-1 -(2-Cyclopropyl-2-fluoro-ethyl)-6-(4-fluoro-3-methyl phenyl)pyrroioi3,2-b]pyridine.

To a solution of compound of (R/S)-1 ~cyciopropyl-2~[6-(4~fluoro~3-methyl~ phenyl)pyrroio[3,2-b]pyridin-1-yl]ethanoi (Example 274, 14 mg, 0.05 mmol) in DCM (1 mL) cooled at 0 °C was added DAST (29 μΐ_, 0.22 mmol). The reaction mixture was warmed to room temperature and after 30 minutes a saturated aqueous solution of NaHCOa was added. The organic phase was separated, dried over MgS0 ₄ , filtered and evaporated to afford the title compound (6.5 mg, 47%). MS (ESI): mass calcd. for C ₉ H ₁₈ F2N ₂ , 312.1; m/z found, 313.1 [M+Hf. H NMR (500 MHz, DMSO-d ₆ ) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.19- 8.15 (m, 1H), 7.72-7.66 (m, 2H), 7.62-7.56 (m, 1H), 7.26 (dd, J = 9.7, 8.5 Hz, 1 H), 6.61 (dd, J = 3.2, 0.8 Hz, 1 H), 4.66 - 4.56 (m, 2H), 4.32 - 4.15 (m, 1H), 2.33 (d, J= 1.9 Hz, 3H), 1.05-0.96 (m, 1H), 0.57-0.48 (m, 2H), 0.45-0.34 (m, 2H). rnethoxyazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 86. MS (ESI): mass calcd. for C20H20FN3O2, 353.2; m/z found, 354.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.64 - 8.60 (m, 1 H), 8.07 (s, 1 H), 7.66 (dd, J = 7.7, 2.4 Hz, 1 H), 7.61 - 7.54 (m, 2H), 7.26 (t, J = 9.1 Hz, 1 H), 6.59 (d, J = 3.3 Hz, 1 H), 5.04 (s, 2H), 4.41 - 4,35 (m, 1 H), 4.31 - 4.22 (m, 1 H), 4.13 - 4.00 (m, 2H), 3.75 - 3.68 (m, 1 H), 3.23 (s, 3H), 2.33 (s, 3H).

Example 291 : 6-(4-Fluoro-3-methyl-phenyl)-1 -(2-methoxyethyl)pyrrolor3,2- blpyridine trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 170 using 6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2-b]pyridine and 1 -bromo-2- methoxyethane. MS (ES!): mass calcd. for C17H17FN2O, 284.1 ; m/z found, 285.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.88 (s, 1 H), 8.76 (s, 1 H), 8.04 (d, J = 3,3 Hz, 1 H), 7,81 (dd, J = 7.6, 2.4 Hz, 1 H), 7.74 - 7,68 (m, 1 H), 7.38 - 7.30 (m, 1 H), 6.76 (d, J = 3.3 Hz, 1 H), 4.58 (t, J = 5.1 Hz, 2H), 3.71 (t, J = 5.1 Hz, 2H), 3.22 (s, 3H), 2.35 (d, J = 1 .9 Hz, 3H). -Cvclobutyl-2-r6-(3-fluorophenyl)pyrrolor3,2-blpyridin-1 ^■

The title compound was prepared in a manner analogous to Example 170 using 6-(3-fluoro-phenyl)-1 H-pyrrolo[3,2-b]pyridine and 2-bromo-1 - cyclobutyiethanone. MS (ESI): mass calcd. for C 9H17F 2O, 308.1; m/z found, 309.1 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) δ 8.61 (d, J = 1.9 Hz, 1 H), 8.01 (s, 1H), 7.58-7.42 (m, 4H), 7.15-7.08 (m, 1H), 6.69 (d, J = 3.3 Hz, 1H), 5,21 (s, 2H), 3.58-3.45 (m, 1H), 2.38-2.25 (m, 2H), 2.24-2.13 (m, 2H), 2.10- 1.97 (m, 1H), 1.92- 1.80 (m, 1H).

Example 293: 2-f6-(4-Fluorophenyl)pyrrolor3,2-blpyridin-1 -yll- -f(3R)-3-

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C19H17F2N3O, 341.1; m/z found, 342.1 [M+H] ⁺ .

Analytical HPLC was obtained on a Agilent 1100 Series using a XBridge C18 column (4.6 x 100mm, δμπη), mobile phase of 10 - 100% ACN in 20mM NH4OH over 8 min and then hold at 100% ACN for 3 min, at a flow rate of 1 mL/min (Temperature = 45 °C). R _t = 5.62 min at 254 nm. -r6-f4-Fluorophenyl)pyrrolof3.2-blpyridin-1 -νΠ-1 (3S)-3-

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass ca!cd. for C19H17F2N3O, 341 , 1 ; m/z found, 342, 1 [M+H] ⁺ . f.

Analytical HPLC was obtained on a Agilent 1 100 Series using a XBridge C18 column (4.6 x 100mm, δμιτι), mobile phase of 10 - 100% ACN in 20mM NH ₄ OH over 8 min and then hold at 100% ACN for 3 min, at a flow rate of 1 mL/min (Temperature = 45 °C). R _t = 5.63 min at 254 nm.

Example 285: 1 -[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yllbutan-

2-one frifiuoroacetafe salt.

The title compound was prepared in a manner analogous to Example 170 using 6-(4~fluoro~3-methyiphenyl)-1 H-pyrrolo[3,2~b]pyridine and 1 - bromobutan-2-one. MS (ESI): mass calcd, for C-isH-iyFNaO, 296, 1 ; m/z found, 297.1 [M+Hf. H NMR (500 MHz, CD ₃ OD) δ 8.86 (d, J = 1 .7 Hz, 1 H), 8.81 (s, 1 H), 8.00 (d, J = 3.3 Hz, 1 H), 7.72 - 7.67 (m, 1 H), 7.65 - 7.59 (m, 1 H), 7.26 - 7.20 (m, 1 H), 6.91 (dd, J = 3.3, 0.9 Hz, 1 H), 5.49 (s, 2H), 2.72 (q, J = 7.3 Hz, 2H), 2.39 (d, J = 2.1 Hz, 3H), 1 .13 (t, J = 7.3 Hz, 3H). -Ethyl-2-i6-(4-fluoro-3-methyl-phenvnpyrrolo[3.2-b]pyridiri- 1 -

TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 6666,. MMSS ((EESSII)):: mmaassss ccaallccdd.. ffoorr CC1199HH2200FFNN33OO,, 332255..22;; mm//zz ffoouunndd,, 332266..11 [[MM++HH]] ^11"" .. AAnnaallyyttiiccaall HHPPLLCC wwaass oobbttaaiinneedd oonn aa AAggiilleenntt 11 110000 SSeerriieess uussiinngg aa XXBBrriiddggee CC1188 ccoolluummnn ((44..66 xx 110000mmmm,, 55μμηηιι)),, mmoobbiillee pphhaassee ooff 1100 -- 110000%% AACCNN iinn 2200mmMM NNHH ₄₄ OOHH oovveerr 88 mmiinn aanndd tthheenn hhoolldd aatt 110000%% AACCNN ffoorr 33 mmiinn,, aatt aa ffllooww rraattee ooff 11 mmLL//mmiinn

((TTeemmppeerraattuurree == 4455 °°CC)).. FF¾¾ == 66..1122 mmiinn aatt 225544 nnmm..

EExxaammppllee 229977:: NN,,NN--DDiieetthhvyll--22--[[66--((44--fflluuoorroo--33--mm eetthhvyll--pphheennyyll))ppyyrrrroollooff33,,22--

The title compound was prepared in a manner analogous to Example 66. MS (ES!): mass calcd. for C20H22FN3O, 339.2; m/z found, 340.1 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-C ) δ 8.60 (d, J = 2.0 Hz, 1 H), 8.02 - 8.00 (m, 1 H), 7.65 (dd, J = 7.6, 2.4 Hz, 1 H), 7.60 (d, J = 3.2 Hz, 1 H), 7.58 - 7.53 (m, 1 H), 7.28 - 7.23 (m, 1 H), 6.57 (dd, J = 3.2, 0.9 Hz, 1 H), 5.25 (s, 2H), 3.47 (q, J = 7.1 Hz, 2H), 3.30 - 3.26 (m, 2H), 2.33 (d, J = 1 .9 Hz, 3H), 1 .24 (t, J = 7.1 Hz, 3H), 1 .03 (t, J = 7.1 Hz, 3H). -(Azetidin-1 -vn-2 3-chioro-8 3

TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 2299.. MMSS ((EESSII)):: mmaassss ccaallccdd.. ffoorr CCiiggHHiissCC!!FFssNNssOO,, 339933..11 ;; mm//zz ffoouunndd,, 339944..00 [[MM++HH]] ⁺⁺ . HH NNMMRR ((440000 MMHHzz,, DDMMSSOO--ccfefe)) δδ 88..8800 ((dd,, JJ == 22..00 HHzz,, 11 HH)),, 88..3344 ((dd,, JJ == 22..00 HHzz,, 11 HH)),, 88..1122 -- 88..0066 ((mm,, 22HH)),, 77..8833 ((ss,, 11 HH)),, 77..7799 -- 77..7755 ((mm,, 22HH)),, 55..0044 ((ss,, 22HH)),, 44..2255 ((tt,, JJ == 77..77 HHzz,, 22HH)),, 33..9911 ((tt,, JJ == 77..77 HHzz,, 22HH)),, 22..3344 -- 22..2244 ((mm,, 22HH))..

ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ES!): mass calcd. for Ci ₉ Hi ₇ ClN ₂ 0, 324.1 ; m/z found, 325.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-C ) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.19 (d, J = 1 .9 Hz, 1 H), 7.79 (s, 1 H), 7.57 (s, 1 H), 7.54 (d, J = 7.8 Hz, 1 H), 7.39 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 H), 5.50 (s, 2H), 2.41 (s, 3H), 2.16 - 2.09 (m, 1 H), 1 .04 - 0.98 (m, 2H), 0.97 - 0.92 (m, 2H).

Example 300: 2-(3-Chloro-6-phenyl-pyrroloi3,2-b]pyridin-1 -vD-1 -cyclopropyi- ethanone.

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for C18H15CIN2O, 310.1 ; m/z found, 31 1 .0 [M+H] ⁺ . ¹ H IMMR (400 MHz, DMSO-cfe) δ 8,74 (d, J = 1 .8 Hz, 1 H), 8.22 (d, J = 1 .9 Hz, 1 H), 7.80 (s, 1 H), 7.78 - 7.73 (m, 2H), 7.55 - 7.47 (m, 2H), 7,45 - 7,37 (m, 1 H), 5.50 (s, 2H), 2.18 - 2.09 (m, 1 H), 1 .04 - 0.97 (m, 2H), 0.97 - 0.92 (m, 2H). Example 301 : 1 -(Azetidin-1 -vn-2-f3-chloro-6-(3,4.5- trifluorophenyl)pyrrolof3.2-blpyridin-1 -yl1ethanone.

The title compound was prepared in a manner analogous to Example 29. MS (ESI): mass calcd. for C18H13CIF3N3O, 379.1 ; m/z found, 380.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.80 (d, J = 2.0 Hz, 1 H), 8.33 (d, J = 1 .9 Hz,

1 H), 7.87 - 7.79 (m, 3H), 5.01 (s, 2H), 4.25 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.6 Hz, 2H), 2.33 - 2.24 (m, 2H).

Exam le 302: 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(4-fluorophenyl)pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 182, MS (ES!): mass calcd. for Ci ₈ Hi ₅ F ₂ IM ₃ 0, 327.1 ; m/z found, 328.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-cfe) δ 8.68 (d, J = 1 .9 Hz, 1 H), 8.18 - 8.16 (m, 1 H), 7.83 - 7.77 (m, 2H), 7.65 (d, J = 2,2 Hz, 1 H), 7,39 - 7.33 (m, 2H), 4.95 (s, 2H), 4.22 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.32 - 2.23 (m, 2H).

Example 303: 1 -(Azetidin-1 -yl)-2-f3-chloro-6-(3,5-dimethylphenyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 29. MS (ESI): mass calcd. for C ₂ oH ₂ oClN ₃ 0, 353.1 ; m/z found, 354.1 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.61 (d, J = 1 .8 Hz, 1 H), 8.05 (d, J = 1 .8 Hz, 1 H), 7,59 (s, 1 H), 7.29 (s, 2H), 7.04 (s, 1 H), 4.98 (s, 2H), 4,30 (t, J = 7.8 Hz, 2H), 4.09 - 4.01 (m, 2H), 2.44 - 2.31 (m, 8H).

Exam le 304: 2-f3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolor3,2-blpyridi n-1 -

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 - morphoiinoethanone (Intermediate 19) and (4-fluoro-3-methylphenyl)boronic acid. MS (ES!): mass calcd. for C20H19F2N3O2, 371 .1 ; m/z found, 372.1

[M+H] ⁺ . Ή NMR (500 MHz, DMSG-d ₆ ) δ 8.65 (d, J = 1 .9 Hz, 1 H), 8.15 (s, 1 H), 7.69 - 7.66 (m, 1 H), 7.63 (d, J = 2.1 Hz, 1 H), 7.61 - 7.55 (m, 1 H), 7.31 - 7.24 (m, 1 H), 5,24 (s, 2H), 3.72 - 3,67 (m, 2H), 3.62 - 3.53 (m, 4H), 3.45 - 3.40 (m, 2H), 2.33 (s, 3H).

Example 305: 2-i3-FluQro-6-(4-fluorophenyl)pyrroloi3 _l 2-blpyriclin-1 -yll-1 - morpholino-ethanone.

F

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 - morpholinoethanone (Intermediate 19) and (4-fluorophenyl)boronic acid. MS (ESi): mass calcd. for C19H17F2N3O2, 357.1 ; m/z found, 358.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-de) δ 8.67 (d, J = 1 .9 Hz, 1 H), 8.19 - 8.16 (m, 1 H), 7.81 - 7.76 (m, 2H), 7.63 (d, J = 2.1 Hz, 1 H), 7.38 - 7.32 (m, 2H), 5.24 (s, 2H), 3.72 - 3.67 (m, 2H), 3.61 - 3.53 (m, 4H), 3.45 - 3.41 (m, 2H).

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fiuoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3-fluoroazetidin-1 - yl)ethanone (Intermediate 17) and (3,4,5~trifiuorophenyi)boronic acid. MS

(ESI): mass calcd. for C18H12F5N3O, 381 .1 ; m/z found, 382.0 [M+H] ⁺ . H NMR (500 MHz, CDC ) δ 8.66 (d, J = 1 .9 Hz, 1 H), 7.64 (t, J = 2.0 Hz, 1 H), 7.25 - 7.20 (m, 3H), 5.40 - 5.19 (m, 1H), 4,73 (s, 2H), 4.42-4.29 (m, 1H), 4.27 4.03 (m, 3H).

Example 307: 1 -(3-Fluoroazetidin-1 -yl)-2-f3-fluoro-6-(4-fluoro-3-methyl-

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3~f!uoro-1 H-pyrrolo[3 _! 2-b]pyridin-1 -yl)-1 -(3-fluoroazetidin-1 - yl)ethanone (Intermediate 17) and (4-fluoro-3-methylphenyl)boronic acid. MS (ESI): masscalcd. for C19H16F3N3O, 359.1; m/z found, 380.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 8.67 (d, J = 1.9 Hz, 1H), 8.15 (t, J = 2.1 Hz, 1H), 7.68 (dd, J = 7.5, 2.4 Hz, 1 H), 7.64 (d, J = 2.1 Hz, 1 H), 7.62 - 7.56 (m, 1 H), 7.31 - 7.25 (m, 1 H), 5.55 - 5.38 (m, 1 H), 5.01 (d, J = 3.4 Hz, 2H), 4.60 - 4.49 (m, 1H), 4.38-4.18 (m, 2H), 4.03-3.91 (m, 1H), 2.33 (d, J = 1.9 Hz, 3H),

Example 308: 1-(3-Fluoroazetidin-1-yl)-2-f3-fluoro-6-(4-

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fluoro-1 H-pyrro!o[3,2-b]pyridin-1 -yl)-1 -(3-f!uoroazetidin-1 - yl)ethanone (Intermediate 17) and (4-fiuorophenyl)boronic acid. MS (ESI): mass calcd. for C18H14F3N3O, 345.1; m/z found, 346.0 [M+H] ⁺ . H IMMR (500 MHz, DMSO-cfe) δ 8.68 (d, J= 1.9 Hz, 1H), 8.17 (t, J = 2.2 Hz, 1H), 7.82- 7.77 (m, 2H), 7.65 (d, J = 2,2 Hz, 1 H), 7.38 - 7.32 (m, 2H), 5.54 - 5.38 (m, 1H), 5.01 (d, J = 3.1 Hz, 2H), 4.60-4.50 (m, 1H), 4.37-4.19 (m, 2H), 4.02- 3.91 (m, 1H). Example 309: 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(4-methyl-2-

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(3-fluoroazeiidin-1 - yi)ethanone (Intermediate 17) and 4,4,5,5-tetramethyl-2-(4-methyithiophen~2- yl)-1,3,2-dioxaborolane. MS (ESI): mass calcd. for Ci7H ₅ F2N ₃ OS, 347.1; m/z found, 348.0 [M+H] ^{+ 1} H NMR (400 MHz, D SO-cfe) δ 8.66 (s, 1H), 8.11 (s, 1H), 7.63 (s, 1H), 7.42 (s, 1H), 7.17 (s, 1H), 5.58-5.37 (m, 1H), 5.00 (s, 2H), 4.63-4.50 (m, 1H), 4,40-4.18 (m, 2H), 4.04-3.90 (m, 1H), 2.26 (s, 3H).

Example 310: 2-[6-f3-(Difluoromethyl)phenyll-3-fluoro-pyrrolo[3 ₁ 2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 92, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 ~(3-fluoroazetidin-1 - yijethanone (Intermediate 17) and (3-(difiuoromethyl)phenyl)boronic acid. MS (ESI): mass calcd. for C19H15F4N3O, 377.1; m/z found, 378.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-de) δ 8.73 (d, J = 1.8 Hz, 1 H), 8.25 (t, J = 2.2 Hz, 1 H), 7.96 -7.91 (ni, 2H), 7,72-7.57 (m, 3H), 7.12 (t, J = 55.8 Hz, 1H), 5.58-5.36 (m, 1H), 5.04 (s, 2H), 4.62-4.49 (m, 1H), 4.39-4.18 (m, 2H), 4.04-3.87 (m, 1H). Example 311 : 2-[6-{3.4-Difluorophenyl)-3-fluoro-pyrroloi3.2-blpyridir¾-1 -yll-1 - -fluoroazetidin-1-yl)ethanone.

The title compound was prepared in a manner analogous to Example 92, using 2~(6-bromo-3~fluoro-1 H-pyrroio[3 _! 2-b]pyridin~1 -yl)-1 ~(3-fluoroazetidin-1 - yl)ethanone (Intermediate 17) and (3,4-difluorophenyl)boronic acid,. MS (ESI): mass calcd. for C ₈ H ₃ F ₄ N ₃ 0, 363.1; m/z found, 364.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-de) δ 8.72 (d, J = 1.9 Hz, 1 H), 8,24 (t, J = 2.2 Hz, 1 H), 7.92 - 7.85 (m, 1 H), 7.68 (d, J = 2.2 Hz, 1 H), 7.65 - 7.54 (m, 2H), 5.57 - 5.36 (m, 1H), 5.02 (s, 2H), 4.62-4.48 (m, 1H), 4.39-4.19 (m, 2H), 4.03-3.90 (m, 1H).

Example 312: 1-(Azetidin-1-yl)-2-i3-chloro-6-i ^' 2,3,4- trifluorophenyl)pyrrolor3,2-blpyridin-1-yllethanone.

The title compound was prepared in a manner analogous to Example 29. MS (ES!): mass calcd. for Ci ₈ H _i3 ClF ₃ N ₃ 0, 379.1 ; m/z found, 379.9 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.55 (s, 1 H), 8.08 (s, 1 H), 7.69 (s, 1 H), 7.46 - 7.35 (m, 1 H), 7,33 - 7,22 (m, 1 H), 5.01 (s, 2H), 4.33 (t, J = 7.8 Hz, 2H), 4.06 (t, J = 7.8 Hz, 2H), 2.47-2.31 (m, 2H). yll-1 -pyrrolidin-1 -yl-ethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(pyrrolidin-1 - yljethanone (Intermediate 18) and (4-fluoro-3-methylphenyl)boronic acid, MS (ESI): mass ca!cd. for C20H19F2N3O, 355, 1 ; m/z found, 356, 1 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8,57 (d, J = 1 .9 Hz, 1 H), 8.09 - 8.04 (m, 1 H), 7.61 - 7.56 (m, 1 H), 7.54 - 7.48 (m, 1 H), 7.46 (d, J = 2.4 Hz, 1 H), 7.14 (t, J = 9.0 Hz, 1 H), 5.13 (s, 2H), 3.65 (t, J = 6.7 Hz, 2H), 3.51 - 3.42 (m, 2H), 2.35 (s, 3H), 2.13 - 2.02 (m, 2H), 1 .98 - 1 .87 (m, 2H).

Example 314: 2-f3-Fluoro-6-(4-fluorophenyl)pyrrolof3,2-b]pyridin-1 -yll-1 - pyrrolidin-1 -yl-ethanone.

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(pyrrolidin-1 - yi)ethanone (Intermediate 18) and (4~fiuorophenyi)boronic acid. MS (ESI): mass calcd, for Ci ₉ H ₁₇ F ₂ N ₃ 0, 341.1 ; m/z found, 342.1 [M+H] ⁺ . Analytical HPLC was obtained on a Agilent 1 100 Series using a XBridge C18 column (4.6 x 100mm, 5μιη), mobile phase of 10 - 100% ACN in 20mM NH ₄ OH over 8 min and then hold at 100% ACN for 3 min, at a flow rate of 1 mL/min

(Temperature = 45 °C). R _t = 5.92 min at 254 nm. -i3-Fiuoro-6-(3,4,5-tnfluorophenyl)pyrroloi3,2-blpyridin-1 -vil-1 ^■

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-1 -(pyrrolidin-1 - yi)ethanone (Intermediate 18) and (3,4,5-trifluorophenyl)boronic acid. MS (ESi): mass calcd. for Ci9H ₅ F4N ₃ 0, 377,1; m/z found, 378,0 [M+H] ⁺ . ^! H NMR (400 MHz, DMSO-ofe) δ 8.61 (d, J = 1.8 Hz, 1H), 8.15 (s, 1H), 7.59- 7.49 (m, 3H), 5.14 (s, 2H), 3.65 (t, J = 6.8 Hz, 2H), 3.45 (t, J = 6.9 Hz, 2H), 2.13 - 2.02 (m,2H), 1.92 (p, J = 6.9 Hz, 2H).

Example 316: 1-Cvclopropyl-2-[3-fluoro-6-(4-fluoro-3-methyl-

The title compound was prepared in a manner analogous to Example 136. MS (ESI): mass calcd. for C ₉ H ₁₆ F ₂ N ₂ 0, 326.1; m/z found, 327.0 [M+H] ⁺ . H NMR (600 MHz, DMSO-fe) δ 8.67 (d, J = 1.9 Hz, 1H), 8.14 (t, J = 2.2 Hz, 1H), 7.69 - 7.66 (m, 1 H), 7.65 (d, J = 2.1 Hz, 1 H), 7.60 - 7.56 (m, 1 H), 7.26 (dd, J = 9.7, 8.5 Hz, 1H), 5.41 (s, 2H), 2.33 (d, J = 1.9 Hz, 3H), 2.12-2.07 (m, 1H), 1.01 - 0.97 (m, 2H), 0.95-0.91 (m, 2H). -Cvclopropyl-2-f3-fluoro-6-(4-methyl-2-thienvnpyrrolor3.2-

The title compound was prepared in a manner analogous to Example 136 substituting 4,4,5,5-tetramethyl-2-(4-methylthiophen-2-yl)-1 ,3,2-dioxaborolane for (3,4-difluorophenyl)boronic acid. MS (ES!): mass calcd. for C17H15FIM2OS, 314.1 ; m/z found, 315.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1 .9 Hz, 1 H), 8.1 1 (s, 1 H), 7.64 (s, 1 H), 7,42 (s, 1 H), 7, 16 (s, 1 H), 5.41 (s, 2H), 2.26 (s, 3H), 2.16 - 2.06 (m, 1 H), 1 .09 - 0.90 (m, 4H).

Example 318: 2-[6-(5-Chloro-2-thienyl)-3-fluoro-pyrrolo[3,2-blpyridin-1 -yll-1 -

The title compound was prepared in a manner analogous to Example 136. MS (ES!): mass calcd. for C16H12CIFN2OS, 334.0; m/z found, 335.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1 .9 Hz, 1 H), 8.14 (t, J = 2.2 Hz, 1 H), 7.68 (d, J = 2.2 Hz, 1 H), 7.47 (d, J = 3.9 Hz, 1 H), 7.21 (d, J = 3.9 Hz, 1 H), 5.41 (s, 2H), 2.15 - 2.06 (m, 1 H), 1 .04 - 0.97 (m, 2H), 0.97 - 0.90 (m, 2H).

The title compound was prepared in a manner analogous to Example 136, MS (ES!): mass calcd. for Ci ₈ H _i4 F ₂ jM ₂ 0, 312.1 ; m/z found, 313.0 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.59 (d, J = 1 .8 Hz, 1 H), 7.99 (t, J = 2.1 Hz, 1 H), 7.73 - 7.67 (m, 2H), 7.46 (d, J = 2,3 Hz, 1 H), 7.27 - 7.19 (m, 2H), 5.35 (s, 2H), 2.16 - 2.08 (m, 1 H), 1 .08 - 1 .02 (m, 4H).

Example 320: 1 -Cyclopropyl-2-i3-fluoro-6-(3,4,5-trifluorophenyl)pyrrQto[3, 2-

The title compound was prepared in a manner analogous to Example 136. MS (ESi): mass calcd. for Ci ₈ H ₁₂ F ₄ N ₂ 0, 348.1 ; m/z found, 349.0 [M+H] ⁺ .

Example 32' ^clopropyl-2-f6-r3-(difluoromethyl)phenyll-3-fluoro-

Pyrrolo[3,2-b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 136. Mi (ESI): mass calcd. for C19H15F3N2O, 344.1 ; m/z found, 345.0 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.65 (d, J = 1 .8 Hz, 1 H), 8.08 (t, J = 2.1 Hz, 1 H), 7.87 - 7.83 (m, 2H), 7.65 - 7.56 (m, 2H), 7.49 (d, J = 2.3 Hz, 1 H), 6.86 (t, J = 56.2 Hz, 1 H), 5.38 (s, 2H), 2.16 - 2.10 (m, 1 H), 1 .08 - 1 .02 (m, -(Azetidin-1 -yl)-2-f3-fluoro-6-(4-methyl-2-thienyl)pyrrolor3.2-

The title compound was prepared in a manner analogous to Example 182 substituting 4,4,5,5-tetramethyl-2-(4-niethyithiophen-2-yl)-1 ,3,2-dioxaborolane for (5~chlorothiophen~2-yl)boronic acid. MS (ESI): mass calcd. for

C iyHieFNaOS, 329.1 ; m/z found, 330.0 [M+H] ⁺ . H NMR (500 MHz, CD ₃ OD) δ 8.61 (d, J = 1 .8 Hz, 1 H), 8.03 (t, J = 2.1 Hz, 1 H), 7.44 (d, J = 2,3 Hz, 1 H), 7,32 (d, J = 1 .3 Hz, 1 H), 7.02 (t, J = 1 .2 Hz, 1 H), 4.92 (s, 2H), 4.32 - 4.28 (m, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.42 - 2.34 (m, 2H), 2.30 (d, J = 1 .1 Hz, 3H).

Example 323: 1 -(Azetidin-1 -yl)-2-r6-r3-(difluoromethyl)phenyl1-3-fluoro-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C19H16F3N3O, 359.1 ; m/z found, 360.1 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.65 (d, J = 1 .8 Hz, 1 H), 8.15 (t, J = 2.1 Hz, 1 H), 7.90 - 7.85 (m, 2H), 7.66 - 7.57 (m, 2H), 7.51 (d, J = 2.3 Hz, 1 H), 6.87 (t, J = 56.2 Hz, 1 H), 4.97 (s, 2H), 4.31 (t, J = 7.8 Hz, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.43 - 2.34 (m, 2H). -[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolor3.2-blpyridin -1 ^■

Step A: 1 -(8-Bromo-3-fiuoro-1 H-pyrroloi3,2-b1pyridin-1 -yl)-3-methylbutan-2- one. The title compound was prepared in a manner analogous to

Intermediate 15, using 6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridine

(Intermediate 6) and 1 -bromo-3-methylbutan-2-one.

Step B: 1 -i3-Fluoro-6-(4-fluoro-3-methyl-phenynpyrrolo[3.2-b]pyridin- 1 -yll-3- methyl-butan-2-one. The title compound was prepared in a manner analogous to Example 92, using 1 -(6-bromo-3-fluoro-1 H-pynOlo[3,2-b]pyridin-1 -yl)-3- methylbutan~2-one and (4-fluoro~3-methylphenyl)boronic acid. MS (ESI): mass calcd, for Ci ₃ H ₁₈ F ₂ N ₂ 0, 328.1 ; m/z found, 329.0 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.57 (d, J = 1 .8 Hz, 1 H), 7.92 (t, J = 2.1 Hz, 1 H), 7.57 - 7.52 (m, 1 H), 7.50 - 7.45 (m, 1 H), 7.41 (d, J = 2.3 Hz, 1 H), 7.14 (dd, J = 9.6, 8.4 Hz, 1 H), 5.27 (s, 2H), 2.90 - 2.82 (m, 1 H), 2.35 (d, J = 2.0 Hz, 3H), 1 .20 (d, J = 6.9 Hz, 6H). -[6-(3-Ethviphenyl)-3-fluoro-pyrroloi3.2-b]pyridin-1 -yll-3

The title compound was prepared in a manner analogous to Example 324. MS (ESI): mass calcd. for C ₂₀ H ₂ FN ₂ G, 324.2; m/z found, 325.1 [M+H] ⁺ . Ή NMR (400 MHz, CD3OD) δ 8.59 (d, J = 1 .8 Hz, 1 H), 7.96 - 7.92 (m, 1 H), 7.51 - 7.48 (m, 1 H), 7.48 - 7.44 (m, 1 H), 7.41 (d, J = 2.4 Hz, 1 H), 7.39 - 7.35 (m, 1 H), 7.26 - 7.22 (m, 1 H), 5.28 (s, 2H), 2.92 - 2.81 (m, 1 H), 2.73 (q, J = 7,6 Hz, 2H), 1 .29 (t, J = 7.5 Hz, 3H), 1 .20 (d, J = 7.2 Hz, 6H).

Example 326: 1 -i6-(3,4-Difluorophenyl)-3-fiuoro-pyrroloi3,2-blpyridin-1 -yll-3- methyl-butan-2-one.

The title compound was prepared in a manner analogous to Example 324. MS (ESI): mass calcd. for C18H15F3N2O, 332.1 ; m/z found, 333.0 [M+H] ⁺ . H !MMR (400 MHz, CD3OD) δ 8.60 (d, J = 1 .8 Hz, 1 H), 7.99 (t, J = 2.1 Hz, 1 H), 7.67 - 7.59 (m, 1 H), 7.52 - 7.47 (m, 1 H), 7.45 (d, J = 2.3 Hz, 1 H), 7.43 - 7,33 (m, 1 H), 5.29 (s, 2H), 2.92 - 2.83 (m, 1 H), 1 .21 (d, J = 6.9 Hz, 6H).

Example 327: 1 -[3-Fluoro-6-(3-fluorophenyl)pyrrolo[3,2-blpyridin-1 -yll-3- methyl-butan-2-one.

The title compound was prepared in a manner analogous to Example 324. MS (ESI): mass calcd. for deH^^O, 314.1 ; m/z found, 315.1 [M+H] ⁺ . ¹ H NMR (400 MHz, CD3OD) δ 8.62 (d, J = 1 .8 Hz, 1 H), 8.00 (s, 1 H), 7.54 - 7.47 (m, 2H), 7.48 - 7.40 (m, 2H), 7.18 - 7.08 (m, 1 H), 5.29 (s, 2H), 2.93 - 2.81 (m, 1 H), 1 .21 (d, J = 7.0 Hz, 6H). -[3-Fluoro-6-r3-(trifluoromethyl)phenyllpyrrolor3,2-blpyridi n-1 ^■

The title compound was prepared in a manner analogous to Example 324. MS (ES!): mass calcd. for Ci ₉ H ₆ F ₄ N ₂ 0 _l 364.1 ; m/z found, 365.0 [M+H] ⁺ . ¹ H NMR

(400 MHz, CD ₃ OD) δ 8.65 (d, J = 1 .8 Hz, 1 H), 8.09 - 8.05 (m, 1 H), 8,01 - 7.93 (m, 2H), 7.73 - 7,68 (m, 2H), 7.47 (d, J = 2.4 Hz, 1 H), 5.32 (s, 2H), 2.93 - 2.82 (m, 1 H), 1 .21 (d, J = 6.8 Hz, 6H).

Example 329: 1 -i3-Fluoro-6-(m-tolyl)pyrroloi3.2-b]pyridin-1 -νΙΙ-3-methyl· butan-2-one.

The title compound was prepared in a manner analogous to Example 324. MS (ESI): mass calcd. for Ci ₉ Hi ₉ FN ₂ 0, 310.1 ; m/z found, 31 1 .1 [M+H] ^{+ 1} H NMR (400 MHz, CD3OD) δ 8.59 (d, J = 1 .8 Hz, 1 H), 7.94 (t, J = 2.1 Hz, 1 H), 7.50 - 7.48 (m, 1 H), 7.47 - 7.43 (m, 1 H), 7.42 (d, J = 2.3 Hz, 1 H), 7.36 (t, J = 7.6 Hz, 1 H), 7.21 (d, J = 7.6 Hz, 1 H), 5.28 (s, 2H), 2.92 - 2.81 (m, 1 H), 2.43 (s, 3H), 1 .20 (d, J = 7.0 Hz, 6H).

The title compound was prepared in a manner analogous to Example 170 using 8~(4-fluoro-3~methyiphenyl)~1 H~pyrrolo[3,2-b]pyridine and chioromethyi methyl sulfide. MS (ESI): mass caicd. for C16H-15FN2S, 288.1 ; m/z found, 287.1 [M+Hf. ¹ H IMMR (500 MHz, DMSO-cfe) δ 8.66 (d, J = 2.0 Hz, 1 H), 8.30 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.78 (d, J = 3.3 Hz, 1 H), 7.71 - 7.68 (m, 1 H), 7.63 - 7.58 (m, 1 H), 7.26 (dd, J = 9,7, 8.5 Hz, 1 H), 6.61 (dd, J = 3.3, 0,9 Hz, 1 H), 5.49 (s, 2H), 3.17 (s, 3H), 2.33 (d, J = 1 .9 Hz, 3H).

Example 331 : (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 - (methylsulfinylmethyl)pyrrolor3,2-blpyridine.

To a solution of compound of 6~(4~fiuoro-3~methyi-phenyi)~1 - (methyisulfanyimethyl)pyrrolo[3,2-b]pyridine (Example 330, 155 mg, 0.54 mmol) in DCM (3 mL) cooled at 0 °C was added HCI 4M (0.16 mL, 0.65 mmol). After 5 minutes, MCPBA (140 mg, 0.81 mmol) was added and the reaction mixture was stirred at 0 °C for 10 minutes. Aqueous saturated solution of NaHCC»3 was added to the mixture and the aqueous phase was extracted 2 times with DCM. The combined organic layers were dried

(MgS0 ₄ ), filtered and evaporated. Purification by HPLC Method A gave the title compound (24 mg, 14%) along with the compound of 6-(4-fluoro-3- methyl~phenyl)-1 ~(methyisuifonylmethyi)pyrrolo[3,2-b]pyridine (Example 332) (14 mg, 8%). MS (ESI): mass calcd. for C 6H15FN2OS, 302.1 ; m/z found, 303.0 [M+Hf. H NMR (500 MHz, D SO-efe) δ 8.68 (d, J = 2.0 Hz, 1 H), 8.34 (dd, J = 2.0, 0.9 Hz, 1 H), 7.71 (d, J = 3.3 Hz, 1 H), 7.69 - 7.66 (m, 1 H), 7.61 - 7.56 (m, 1 H), 7.27 (dd, J = 9.7, 8.5 Hz, 1 H), 6.70 (dd, J = 3.3, 0.9 Hz, 1 H), 5.69 (d, J = 13.5 Hz, 1 H), 5.45 (d, J = 13.5 Hz, 1 H), 2.57 (s, 3H), 2.33 (d, J = 1 .8 Hz, 3H). -(4-Fluoro-3-methyl-phenyl)-1

The title compound was prepared as described in Example 331 . MS (ESI): mass calcd. for C16H15FN2O2S, 318, 1 ; m/z found, 319,0 [M+H] ⁺ . ^! H N!VfR (500 MHz, DMSO-de) δ 8.70 (d, J = 2.0 Hz, 1 H), 8.39 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.75 (d, J = 3.4 Hz, 1 H), 7.69 (dd, J = 7.8, 2.4 Hz, 1 H), 7.62 - 7.57 (m, 1 H), 7.31 - 7.25 (m, 1 H), 6.75 (dd, J = 3.4, 0.9 Hz, 1 H), 5.91 (s, 2H), 2.95 (s, 3H), 2.33 (d, J = 1 .8 Hz, 3H).

Example 333: 1 -i3-Fluoro-8-(4-fluorophenyl)pyrrolo[3,2-blpyridin-1 -yllbutan-2 one.

Step A: 1 -(8-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -vQbutan-2-one. The title compound was prepared in a manner analogous to Intermediate 15, using 6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridine (Intermediate 6) and 1 - bromobutan~2-one.

Step B: 1 -i3-Fluoro-8-(4-fluorophenyl)pyrroloi3,2-blpyridin-1 -yl]butan-2-one. The title compound was prepared in a manner analogous to Example 1 , Step A, using 1 -(6-bromo-3-fluoro-1 H-pyrrolo[3,2-b]pyridin-1 -yl)butan-2-one and (4- fluorophenyl)boronic acid. MS (ESI): mass calcd. for C17H14F2N2O, 300.1 ; m/z found, 301 .0 [M+H] ⁺ . H NMR (400 MHz, DMSO-d ₆ ) δ 8.68 (d, J = 1 .9 Hz, 1 H), 8.16 (t, J = 2.2 Hz, 1 H), 7.81 - 7.75 (m, 2H), 7.61 (d, J = 2,2 Hz, 1 H), 7,38 - 7.30 (m, 2H), 5.22 (s, 2H), 2.60 - 2.53 (m, 2H), 0.98 (t, J = 7.3 Hz, 3H). -i3-Fluoro-6-(3,4,5-trifluorophenyl)pyrroloi3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 333. MS (ESI): mass calcd. for Ci ₇ H ₁₂ F ₄ N ₂ 0, 336.1 ; m/z found, 337.0 [M+H] ⁺ H NMR (500 MHz, DMSO-ds) δ 8.77 (d, J = 1 .9 Hz, 1 H), 8.28 (t, J = 2.2 Hz, 1 H), 7.84 - 7.77 (m, 2H), 7.68 (d, J = 2.2 Hz, 1 H), 5.22 (s, 2H), 2.56 (q, J = 7.3 Hz, 2H), 0.99 (t, J = 7.3 Hz, 3H). Example 335: 1 -i3-Fluoro-6-(4-fluoro-3-niethyl-phenyl)pyrroloi3,2-blpyridi n-1 -

The title compound was prepared in a manner analogous to Example 333. MS (ESI): mass calcd. for 314.1 ; m/z found, 315.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-cfe) δ 8.67 (d, J = 1 .8 Hz, 1 H), 8.16 - 8.13 (m, 1 H), 7.67 (dd, J = 7.8, 2.1 Hz, 1 H), 7.63 - 7.54 (m, 2H), 7.27 (t, J = 9.1 Hz, 1 H), 5.22 (s, 2H), 2.55 (q, J = 7.3 Hz, 2H), 2.33 (s, 3H), 0.98 (t, J = 7.3 Hz, 3H).

Example 336: 1 -i6-(3,4-Difluorophenyl)-3-fluoro-pyrroloi3,2-blpyridin-1 - yl]butan-2-one.

The title compound was prepared in a manner analogous to Example 333. MS (ESI): mass calcd. for Ci7Hi ₃ F ₃ IM ₂ 0, 318.1 ; m/z found, 319.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ds) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.22 (t, J = 2.2 Hz, 1 H), 7.90 - 7.84 (m, 1 H), 7.64 (d, J = 2.1 Hz, 1 H), 7.63 - 7.60 (m, 1 H), 7.60 - 7.53 (m, 1 H), 5.22 (s, 2H), 2.56 (q, J = 7.3 Hz, 2H), 0.98 (t, J = 7.3 Hz, 3H).

Example 337: 1 -[6-f3-(Difluoromethyl)phenyl1-3-fluoro-pyrrolof3,2-blpyridi n-1 - vnbutan-2-one.

The title compound was prepared in a manner analogous to Example 333. MS (ESI): mass calcd. for C18H15F3N2O, 332.1 ; m/z found, 333.1 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.65 (d, J = 1 .8 Hz, 1 H), 8.09 (t, J = 2.1 Hz, 1 H), 7.88 - 7.82 (m, 2H), 7.65 - 7.55 (m, 2H), 7.46 (d, J = 2.3 Hz, 1 H), 6.85 (t, J = 56.2 Hz, 1 H), 5.19 (s, 2H), 2.62 (q, J = 7.3 Hz, 2H), 1 .09 (t, J = 7.3 Hz, 3H).

Example 338: 1 -[6-(5-Chloro-2-thienyl)-3-fluoro-pyrrolo[3,2-blpyridin-1 - yllbutan-2-one.

The title compound was prepared in a manner analogous to Example 333. MS (ESI): mass calcd. for Ci5H ₂ CIFN ₂ OS, 322.0; m/z found, 323.0 [M+Hf. ¹ H NMR (500 MHz, CD ₃ OD) δ 8.57 (d, J = 1 .8 Hz, 1 H), 7.98 (t, J = 2.1 Hz, 1 H), 7.43 (d, J = 2.3 Hz, 1 H), 7.30 (d, J = 3.9 Hz, 1 H), 7.02 (d, J = 3.9 Hz, 1 H), 5.16 (s, 2H), 2.61 (q, J = 7.3 Hz, 2H), 1 .10 (t, J = 7.3 Hz, 3H). -[3-Fluoro-6-(4-methyl-2-thienyl)pyrrolor3,2-blpyridin-1 ^■

The title compound was prepared in a manner analogous to Example 333. MS (ESI): mass calcd. for Ci ₆ H ₁₅ FN ₂ OS, 302.1 ; m/z found, 303.0 [M÷ } H NMR (500 MHz, CD3OD) δ 8.61 (d, J = 1 .8 Hz, 1 H), 7.97 (t, J = 2.1 Hz, 1 H), 7.40 (d, J = 2.3 Hz, 1 H), 7.31 (d, J = 1 .4 Hz, 1 H), 7.03 - 6.99 (m, 1 H), 5.15 (s, 2H), 2.61 (q, J = 7.3 Hz, 2H), 2.29 (d, J = 1 .1 Hz, 3H), 1 .09 (t, J = 7.3 Hz, 3H). -f6-(4-Fluorophenyl)pyrrolof3,2-blpyridin-1 -yllbutan-2-one.

To a solution of compound of 6-(4-fluorophenyl)-1 H-pyrrolo[3,2-b]pyridine (Example 27, step a, 30 mg, 0.14 mmol), gold (HI) chloride (2 mg, 0.007 mmol) and silver trifluoromethanesulfonate (4 mg, 0.014 mmol) in DCE (1 .5 mL) was added methyl vinyl ketone (35 μΙ_, 0.42 mmol). The reaction mixture was heated to 100 °C. After 1 hour the reaction mixture was cooled to room temperature and solids were filtered. Solvent was then evaporated and the crude was purified by HPLC Method A to afford the title compound (1 mg, 2%). MS (ESI): mass caicd. for C17H15FN2O, 282.1 ; m/z found, 283.1 [M+H] ⁺ . H !MMR (500 IV1Hz, CD ₃ OD) δ 8.54 (d, J = 1 .9 Hz, 1 H), 8.16 - 8.14 (m, 1 H), 7.76 - 7.72 (m, 2H), 7.61 (d, J = 3.3 Hz, 1 H), 7.26 - 7.21 (m, 2H), 6.60 (d, J = 3.2 Hz, 1 H), 4.52 (t, J = 6.5 Hz, 2H), 3.09 (t, J = 6.4 Hz, 2H), 2.12 (s, 3H). -[3-Fluoro-6-(4-fluorophenyl)pyrrolor3,2-blpyridin-1 -yll-3-

The title compound was prepared in a manner analogous to Example 324. MS (ES!): mass calcd. for C18H16F2N2O, 314.1; m/z found, 315.0 [M+H] ⁺ . ^! H NMR (400 MHz, DMSO-C ) δ 8.68 (d, J = 1.9 Hz, 1 H), 8.12 (t, J = 2.2 Hz, 1 H), 7.81 - 7.75 (m, 2H), 7.63 (d, J = 2.2 Hz, 1 H), 7.38 - 7.32 (m, 2H), 5.36 (s, 2H), 2.86 - 2.78 (m, 1 H), 1.12 (d, J = 6.9 Hz, 6H).

The title compound was prepared in a manner analogous to Example 324. MS (ESI): mass calcd. for C19H17F3N2O, 346.1; m/z found, 347.1 [M+H] ⁺ . H N R (400 MHz, DMSO-cfe) δ 8.72 (d, J = 1.9 Hz, 1H), 8.19 (t, J = 2.2 Hz, 1H), 7.94 -7.89 (m, 2H), 7.69-7.63 (m, 2H), 7.62-7.58 (m, 1H), 7.11 (t, J = 55.8 Hz, 1 H), 5.38 (s, 2H), 2.87 - 2.77 (m, 1 H), 1.12 (d, J = 6.9 Hz, 6H).

The title compound was prepared in a manner analogous to Example 324. MS (ES!): mass calcd. for Ci ₇ H _{i 7} FN ₂ OS, 316.1 ; m/z found, 317.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-ds) δ 8.65 (d, J = 1 .8 Hz, 1 H), 8.04 (s, 1 H), 7.61 (d, J = 2.2 Hz, 1 H), 7.40 (s, 1 H), 7.16 (s, 1 H), 5.35 (s, 2H), 2.87 - 2.78 (m, 1 H), 2.26 (s, 3H), 1 .13 (d, J = 6.9 Hz, 6H).

Example 344: 1 -[3-Fluoro-6-(3,4,5-trifluorophenyl)pyrrolor3,2-blpyridin-1 ~yl]-3~ methyl-butan-2-one.

The title compound was prepared in a manner analogous to Example 324. MS (ESI): mass calcd. for Ci ₈ H ₁ F ₄ N ₂ 0, 350.1 ; m/z found, 351 .0 [M+H] ⁺ . H NMR (400 MHz, DMSO-ds) δ 8.77 (d, J = 1 .9 Hz, 1 H), 8.25 (t, J = 2.2 Hz, 1 H), 7.84 - 7.76 (m, 2H), 7.69 (d, J = 2.2 Hz, 1 H), 5.35 (s, 2H), 2.87 - 2.79 (m, 1 H), 1 .13 (d, J = 6.9 Hz, 6H).

Example 345: 1 -[6-(5-Chloro-2-thienyl)-3-fluoro-pyrrolo[3,2-blpyridin-1 -yll-3- methyl-butan-2-one.

The title compound was prepared in a manner analogous to Example 324. MS

(ESI): mass calcd. for 0 ₁₆ Η ₁₄ αΡΝ ₂ Ο8, 336.0; m/z found, 337.0 [IV1+H] ^÷ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.58 (d, J = 1 .8 Hz, 1 H), 7.92 (t, J = 2.1 Hz, 1 H), 7.44 (d, J = 2.3 Hz, 1 H), 7.30 (d, J = 3.9 Hz, 1 H), 7.02 (d, J = 3.8 Hz, 1 H), 5.27 (s, 2H), 2.93 - 2.82 (m, 1 H), 1 .21 (d, J = 7.0 Hz, 6H). -[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-1 ^■

The title compound was prepared in a manner analogous to Example 66. S (ESI): mass calcd. for C20H20FN3O2, 353.2; m/z found, 354.2 [M+H] ⁺ . H NMR (400 MHz, DMSO-d ₆ ) δ 8.61 (d, J = 2.0 Hz, 1 H), 8.07 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.69 - 7.62 (m, 1 H), 7.61 - 7.52 (m, 2H), 7.26 (dd, J = 9.7, 8.5 Hz, 1 H), 6.59 (dd, J = 3.3, 0.8 Hz, 1 H), 5.29 (s, 2H), 3.74 - 3.66 (m, 2H), 3.63 - 3.56 (m, 4H), 3.48 - 3.42 (m, 2H), 2.33 (d, J = 1 .9 Hz, 3H).

phenyl)pyrrolor3,2-blpyridin-1 -vnethanone.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C19H17F2N3O, 341 .1 ; m/z found, 342.1 [M+H] ⁺ . H NMR (600 MHz, DMSO-de) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.07 (d, J = 2.0 Hz, 1 H), 7.69 - 7.64 (m, 1 H), 7.62 - 7.54 (m, 2H), 7.30 - 7.22 (m, 1 H), 6.60 (d, J = 3.3 Hz, 1 H), 5.54 - 5.38 (m, 1 H), 5,06 (d, J = 5.3 Hz, 2H), 4.59 - 4.47 (m, 1 H), 4.36 - 4.19 (m, 2H), 4.03 - 3.91 (m, 1 H), 2.33 (s, 3H). Example 348: N-Cvclopropyl-2-f6-(4-fluoro-3-methyl-phenyl)pyrrolor3,2-

;etamide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for CigHisFNaG, 323.1 ; m/z found, 324.2 [M+H] ⁺ Ή NMR (600 MHz, DMSO-efe) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.32 (d, J = 4.2 Hz, 1 H), 8.06

- 8.01 (m, 1 H), 7.66 (dd, J = 7,5, 2.5 Hz, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 7.59 - 7.54 (m, 1 H), 7.29 - 7.23 (m, 1 H), 6.58 (d, J = 3.2 Hz, 1 H), 4.86 (s, 2H), 2.69

- 2.62 (m, 1 H), 2.33 (s, 3H), 0.67 - 0.60 (m, 2H), 0.47 - 0.42 (m, 2H).

blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for Ci ₉ Hi ₈ FN ₃ 0, 323.1 ; m/z found, 324.2 [M+H] ⁺ ' H NMR (400 MHz, DMSO-de) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.07 (dd, J = 2.0, 0.9 Hz, 1 H), 7.68 (dd, J = 7.6, 2.3 Hz, 1 H), 7.62 - 7.55 (m, 2H), 7.27 (dd, J = 9.7, 8.5 Hz, 1 H), 6.59 (dd, J = 3.3, 0.9 Hz, 1 H), 5.00 (s, 2H), 4.20 (t, J = 7,7 Hz, 2H), 3.91 (t, J = 7.8 Hz, 2H), 2.34 (d, J = 1.9 Hz, 3H), 2.31 - 2.21 (m, 2H).

The compound of Example 349 can also be prepared from the compound of Example 68 in the presence of 10 wt.% Pd/C in methanol at room

temperature under H ₂ atmosphere. -Cvclopropyl-2-i6-(3,5-difiuorophenvnpyrrolo[3,2-b]pyridir¾ -1 -

The title compound was prepared in a manner analogous to Example 75. MS (ESi): mass calcd. for C ₈ H ₁₅ F ₂ N ₃ 0, 327.1 ; m/z found, 328.1 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-ofe) δ 9.03 (s, 1 H), 8.89 (s, 1 H), 8.43 - 8.36 (m, 1 H), 8.1 1 - 8.06 (m, 1 H), 7.72 - 7.65 (m, 2H), 7.40 - 7.32 (m, 1 H), 6.87 - 6.78 (m, 1 H), 5.08 (s, 2H), 2.70 - 2.59 (m, 1 H), 0.67 - 0.59 (m, 2H), 0.49 - 0.42 (m, 2H). Example 351 : N-Cvclopropyl-2-f6-f3-(trifluoromethyl)phenyllpyrrolof3,2-

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C19H16F3N3O, 359.1 ; m/z found, 360.1 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 9.05 - 9.01 (m, 1 H), 8.85 (s, 1 H), 8.42 (d, J = 4.2 Hz, 1 H), 8.21 - 8.14 (m, 2H), 8.07 (d, J = 3.2 Hz, 1 H), 7.87 - 7.79 (m, 2H), 6.83 (d, J = 3,3 Hz, 1 H), 5,09 (s, 2H), 2.70 - 2.62 (m, 1 H), 0.68 - 0.61 (m, 2H), 0.49 - 0.43 (m, 2H). Example 352: N-Cvclopropyl-2-r6-f2-fluoro-3-

(trifluoromethyl)phenyllpyrrolo[3,2-b]pyridin-1 -yl1acetamide trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 75. MS (ES!): mass calcd. for C19H15F4N3O, 377.1 ; m/z found, 378.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ds) δ 8.79 (s, 1 H), 8.56 (s, 1 H), 8.39 (d, J = 4.2 Hz, 1 H), 8.06 - 7.98 (m, 2H), 7,90 (t, J = 6.8 Hz, 1 H), 7.61 (t, J = 7.8 Hz, 1 H), 6.81 (d, J = 3.2 Hz, 1 H), 5.02 (s, 2H), 2.68 - 2.60 (m, 1 H), 0.67 - 0.60 (m, 2H), 0.47 - 0.41 (m, 2H).

Example 353: 1 -(Azetidin-1 -yl)-2-f6-(4-fluorophenyl)pyrrolof3,2-blpyridin-1 - yllethanone.

The title compound was prepared in a manner analogous to Example 71 . MS (ES!): mass calcd. for Ci ₈ Hi ₆ FN ₃ 0, 309.1 ; m/z found, 310.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.63 (d, J = 1 .9 Hz, 1 H), 8.09 (d, J = 1 .7 Hz, 1 H), 7.83 - 7.75 (m, 2H), 7.60 (d, J = 3.2 Hz, 1 H), 7.39 - 7.31 (m, 2H), 6.60 (dd, J = 3.3 0.9 Hz, 1 H), 5.00 (s, 2H), 4.25 - 4.17 (m, 2H), 3.94 - 3.88 (m, 2H), 2.32 - 2.23 (m, 2H).

Example 354: 1 -(Azetidin-1 -yl)-2-(6-phenylpyrroio[3,2-b]pyridin-1 - vDethanone.

The title compound was prepared in a manner analogous to Example / 1. MS (ESI): mass calcd. for C18H17N3O, 291 .1 ; m/z found, 292,2 [M+H] ⁺ . H NMR (400 MHz, DMSO- fe) δ 8.66 (d, J ^ 2.0 Hz, 1 H), 8.1 1 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.77 - 7.73 (m, 2H), 7.60 (d, J = 3.3 Hz, 1 H), 7.54 - 7.48 (m, 2H), 7.42 - 7.36 (m, 1 H), 6.60 (dd, J = 3.2, 0.9 Hz, 1 H), 5.01 (s, 2H), 4.21 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.8 Hz, 2H), 2.32 - 2.20 (m, 2H). 1 -vnethanone.

The title compound was prepared in a manner analogous to Example 71 . MS (ESI): mass calcd, for C18H15F2N3O, 327.1 ; m/z found, 328.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.74 (d, J = 2.0 Hz, 1 H), 8.25 (dd, J = 2.0, 0.9 Hz, 1 H), 7.85 (d, J = 3.3 Hz, 1 H), 7.60 - 7.52 (m, 2H), 7.28 - 7.19 (m, 1 H), 6.62 (dd, J = 3.3, 0.8 Hz, 1 H), 5.02 (s, 2H), 4.22 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.33 - 2.22 (m, 2H).

Example 356: 1 -(Azetidin-1 -yl)-2-r6-(m olyl)pyrrolor3.2-blpyridin-1 - yljethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 71 . MS (ESI): mass calcd. for Ci ₉ H ₁₉ N ₃ 0, 305.2; m/z found, 306.2 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-ds) δ 8.97 (d, J = 1 .6 Hz, 1 H), 8.87 (s, 1 H), 8.06 (d, J = 3,3 Hz, 1 H), 7.69 - 7.61 (m, 2H), 7.47 (t, J = 7,6 Hz, 1 H), 7,31 (d, J = 7.6 Hz, 1 H), 6.85 (d, J = 3.4 Hz, 1 H), 5.23 (s, 2H), 4.29 (t, J = 7.6 Hz, 2H), 3.93 (t, J = 7.7 Hz, 2H), 2.44 (s, 3H), 2.37 - 2,25 (m, 2H), -(Azetidin-1 -yl)-2-f6-(3,4-dichlorophenvnpyrrolof3.2-blpyridin-

The title compound was prepared in a manner analogous to Example 71 . MS (ESI): mass calcd. for C ₁₈ H ₁₅ Ci ₂ N ₃ 0, 359.1 ; m/z found, 360.1 [M+Hf. Ή NMR (400 MHz, DMSO-C ) δ 9.00 (d, J = 1 .8 Hz, 1 H), 8.84 (s, 1 H), 8.17 (d, J = 1 .9 Hz, 1 H), 8.02 (d, J = 3.3 Hz, 1 H), 7.91 - 7.81 (m, 2H), 6.83 (d, J = 3.2 Hz, 1 H), 5.19 (s, 2H), 4.28 (t, J = 7.7 Hz, 2H), 3.93 (t, J = 7.7 Hz, 2H), 2.37 - 2.25 (m, 2H).

Example 358: 1 -(Azetidin-1 -yi)-2-i6-f2-fluQro-3-

The title compound was prepared in a manner analogous to Example 71 . MS (ES!): mass calcd. for C19H15F4N3O, 377.1 ; m/z found, 378.1 [M+Hf. H HMR (400 MHz, DMSO-de) δ 8.84 (s, 1 H), 8.67 (s, 1 H), 8.07 - 7.99 (m, 2H), 7.92 (t, J = 7.2 Hz, 1 H), 7,62 (t, J = 7.8 Hz, 1 H), 6.85 (d, J = 3.3 Hz, 1 H), 5.17 (s, 2H), 4.27 (t, J = 7.7 Hz, 2H), 3.92 (t, J = 7.7 Hz, 2H), 2.36 - 2.24 (m, 2H). Example 359: 1 -(Azetidin-1 -yl)-2-f6-(4-methyl-2-thienyl)pyrrolof3 ₁ 2-blpyridin-

1 -yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 71 substituting 4,4,5,5-tetramethyl-2~(4-methylthiophen~2-yi)~1 ,3,2-dioxaboroiane for (2-fluorophenyl)boronic acid, MS (ESI): mass calcd. for C17H17N3OS, 31 1.1 ; m/z found, 312.1 [M+H] ⁺ . H NMR (400 MHz, DMSO- fe) δ 8.86 (s, 1 H), 8.58 (s, 1 H), 7.93 (s, 1 H), 7.56 - 7.50 (m, 1 H), 7.29 - 7.23 (m, 1 H), 6.76 (s, 1 H), 5.15 (s, 2H), 4.28 (t, J = 7.7 Hz, 2H), 3.93 (t, J = 7.7 Hz, 2H), 2.37 - 2.25 (m, 5H).

Example 360: 1 -(Azetidin-1 -yl)-2-r3-chloro-6-(4-fluoro-3-methv

pheny0pyrroloi3,2~blpyridin-1 ~yllethanone.

The title compound was prepared in a manner analogous to Example 176. MS (ESI): mass calcd. for C19H17CIFN3O, 357.1 ; m/z found, 358.1 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-d ₆ ) δ 8.70 (d, J = 1 .9 Hz, 1 H), 8.19 (d, J = 1 .9 Hz, 1 H), 7.78 (s, 1 H), 7.72 - 7.66 (m, 1 H), 7.64 - 7.56 (m, 1 H), 7.28 (dd, J = 9.7, 8.5 Hz, 1 H), 5.01 (s, 2H), 4.24 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.34 (d, J = 1 .9 Hz, 3H), 2.32 - 2.24 (m, 2H).

The title compound was prepared in a manner analogous to Example 106. MS (ESI): mass calcd. for C18H13F4N3O, 363.1 ; m/z found, 364.2 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) 5 8.60 - 8.57 (m, 1 H), 8.10 (dd, J = 1 .9, 1 .0 Hz, 1 H), 7.68 - 7.61 (ni, 1 H), 7.58 (dd, J = 3.4, 0.9 Hz, 1 H), 7.54 - 7,48 (m, 1 H), 7.42 - 7.33 (m, 1 H), 6.70 - 6.66 (m, 1 H), 5.12 (s, 2H), 4.66 (t, J = 1 1 .9 Hz, 2H), 4.41 (t, J ⁼ 12,2 Hz, 2H), Example 362: 1 -(Azetidin-1 -yl)-2-f6-[6-(trifluoromethyl)-2-pyridyllpyrrolo[3.2' b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 102 substituting 2-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-6- (trifluoromethyl)pyridine for (5-(trifluoromethyl)pyridin-3-yl)boronic acid. MS

(ESI): mass calcd. for Ci ₈ H ₁₅ F ₃ N40, 360.1 ; m/z found, 361 .2 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 9.08 (dd, J = 1 .9, 0.9 Hz, 1 H), 8.53 (s, 1 H), 8.22 (d, J = 8.1 Hz, 1 H), 8.08 (t, J = 7.9 Hz, 1 H), 7.72 (d, J = 7.7 Hz, 1 H), 7.63 (dd, J = 3.3, 0.8 Hz, 1 H), 6.69 (dd, J = 3.2, 1 .0 Hz, 1 H), 5.02 (s, 2H), 4.30 (t, J = 7.7 Hz, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.43 - 2.30 (m, 2H).

Example 363: 1 -(Azetidin-1 -yl)-2-f6-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for C18H14F3N3O, 345.1 ; m/z found, 346.1 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) 5 8.57 (d, J = 1 .9 Hz, 1 H), 8.10 - 8.06 (m, 1 H), 7.58 (d, J = 3.3 Hz, 1 H), 7.56 - 7.46 (m, 2H), 6.67 (d, J = 3.3 Hz, 1 H), 5.00 (s, 2H), 4.28 (t, J = 7.7 Hz, 2H), 4.06 (t, J = 7.8 Hz, 2H), 2.42 - 2.31 (m, 2H). Example 364: 1 -[6-(3.5-Difluorophenyl)pyrrolof3,2-blpyridin-1 -νΠ-3-methyl· buian-2~one.

The title compound was prepared in a manner analogous to Example 75. MS (ESI): mass calcd. for C ₈ Hi ₆ F ₂ N ₂ 0, 314.1 ; m/z found, 315.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-de) δ 8.75 (d, J = 2.0 Hz, 1 H), 8.20 (dd, J = 2.2, 0.9 Hz, 1 H), 7.63 (d, J = 3.3 Hz, 1 H), 7.60 - 7.51 (m, 2H), 7.28 - 7.19 (m, 1 H), 6.64 (dd, J = 3.3, 0.9 Hz, 1 H), 5.42 (s, 2H), 2.91 - 2.78 (m, 1 H), 1 .14 (d, J = 6.9 Hz, 6H). Example 365: 1 -Cvclobutyl-2-i6-(4-fluorophenyl)pyrroloi3,2-b]pyridin-1 - yi]ethanone.

The title compound was prepared in a manner analogous to Example 170 using 6~(4-fluoro-phenyl)~1 H~pyrrolo[3,2-b]pyridine and 2-bromo-1 - cyclobutylethanone. MS (ESI): mass calcd. for C19H17FN2O, 308.1 ; m/z found, 309.2 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 7.94 - 7.89 (m, 1 H), 7.72 - 7.64 (m, 2H), 7.51 (d, J = 3.3 Hz, 1 H), 7.25 - 7.16 (m, 2H), 6.67 (dd, J = 3.4, 1 .0 Hz, 1 H), 5.21 - 5.13 (m, 2H), 3.55 - 3.43 (m, 1 H), 2.37 - 2.23 (m, 2H), 2.22 - 2.1 1 (m, 2H), 2.09 - 1 .95 (m, 1 H), 1 .91 - 1 .79 (m, 1 H). -Cvclopropyl-2-i6-(3-ethviphenyl)pyrroioi3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N-cyclopropylacetamide

(intermediate of Step A, Example 75) and (3-ethylpheny!)boronic acid. MS (ESI): mass calcd. for C ₂₀ H ₂ i N ₃ 0, 319.2; m/z found, 320.2 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-de) δ 8.65 (d, J = 1 .9 Hz, 1 H), 8.37 (d, J = 4.2 Hz, 1 H), 8.04 (dd, J = 2.0, 0.9 Hz, 1 H), 7.63 (d, J = 3.2 Hz, 1 H), 7.59 - 7.51 (m, 2H), 7.41 (t, J = 7.6 Hz, 1 H), 7,23 (d, J = 7.6 Hz, 1 H), 6.59 (d, J = 3.6 Hz, 1 H), 4.87 (s, 2H), 2.75 - 2.61 (m, 3H), 1 .26 (t, J = 7.6 Hz, 3H), 0.67 - 0.59 (m, 2H), 0.48 - 0.41 (m, 2H).

Example 367: 2-[6-(3.4-Difluorophenyl)pyrrolof3,2-blpyridin-1 -yll-1 -pyrroisdin 1 -yl-ethanone.

The title compound was prepared in a manner analogous to Example 105. MS (ESI): mass calcd. for Ci ₉ Hi ₇ F ₂ jM ₃ 0, 341 .1 ; m/z found, 342.2 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.53 (d, J = 1 .9 Hz, 1 H), 8.03 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.60 (ddd, J = 12.0, 7.6, 2.3 Hz, 1 H), 7.54 (d, J = 3.3 Hz, 1 H), 7.49 - 7,43 (m, 1 H), 7.37 - 7.29 (m, 1 H), 6.65 (dd, J = 3.3, 0.9 Hz, 1 H), 5.13 (s, 2H), 3.62 (t, J = 6.8 Hz, 2H), 3.44 (t, J = 6,9 Hz, 2H), 2.10 - 2.00 (m, 2H), 1 .95 - 1 .85 (m, 2H). Example 368: 1 -(3,3-Difluoroazetidin-1 -yl)-2-f6-f4-methyl-2-

^ilethar

Step A: Ethyl 2-(6-bromo-1 H-pyrroiof3,2-b]pyridin-1 -yl)acetate. The title compound was prepared in a manner analogous to Example 66 Step B. !VIS (ESI): mass calcd. for CnH n Br^Cb, 282.0; m/z found, 283.0 [M+H] ⁺

The title compound was prepared in a manner analogous to Example 66 Step A. MS (ES!): mass calcd. for C14H12N2O2S, 272.1 ; m/z found, 273.1 [M+H] ⁺ . Step C: 1 -(3,3-Difiuoroazetidin-1 -yl)-2-f6-(4-methyl-2-thienyl)pyrrolof3.2- blpyridin-1 -yllethanone. The title compound was prepared in a manner analogous to Example 31 Step D, MS (ESI): mass calcd. for Ci ₇ H ₅ F ₂ N ₃ 0S, 347.1 : m/z found, 348.1 [M+Hf. ¹ H NMR (400 MHz, CD ₃ OD) δ 8.58 (d, J = 1 .9 Hz, 1 H), 8.03 (dd, J = 2.0, 0.9 Hz, 1 H), 7.52 (d, J = 3.3 Hz, 1 H), 7.28 (d, J = 1 .4 Hz, 1 H), 6.99 - 6.97 (m, 1 H), 6.64 (dd, J = 3.3, 0.9 Hz, 1 H), 5.08 (s, 2H), 4.64 (t, J = 1 1 .9 Hz, 2H), 4.40 (t, J = 12.2 Hz, 2H), 2.29 (s, 3H). -i6-(4-Methyi-2-thienyl)pyrroloi3,2-b]pyridin-1 -yll-1 -pyrroiidin

The title compound was prepared in a manner analogous to Example 368. MS (ESI): mass calcd. for C ₈ H ₁₃ N ₃ 0S, 325.1 ; m/z found, 326.2 [M+Hf. Ή NMR (400 MHz, CD3OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 8.00 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.51 (d, J = 3.3 Hz, 1 H), 7.27 (d, J = 1 .3 Hz, 1 H), 6.97 (s, 1 H), 6.62 (dd, J = 3.3, 0.9 Hz, 1 H), 5.13 (s, 2H), 3,63 (t, J = 6.8 Hz, 2H), 3.46 (t, J = 6.9 Hz, 2H), 2.28 (s, 3H), 2.13 - 2.00 (m, 2H), 1 .97 - 1 .86 (m, 2H).

Example 370: 1 -(3-Fluoroazetidin-1 -yl)-2-f6-(4-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 368. MS (ESI): mass calcd. for Ci7Hi ₆ FN ₃ OS, 329, 1 ; m/z found, 330,2 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.58 (d, J = 1 .9 Hz, 1 H), 8.01 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.52 (d, J = 3.3 Hz, 1 H), 7.28 (d, J = 1 .4 Hz, 1 H), 6.98 (s, 1 H), 6.64 (dd, J = 3.4, 0.9 Hz, 1 H), 5.51 - 5.26 (m, 1 H), 5.02 (s, 2H), 4.60 - 4.42 (m, 1 H), 4.41 - 4.22 (m, 2H), 4.18 - 4.00 (m, 1 H), 2.29 (s, 3H).

Example 371 : 1 -(3-Fluoroazetidin-1 -yl)-2-f6-(3,4,5-trifluorophenyl)pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 128. MS (ESI): mass calcd. for Ci ₈ H ₁₃ F ₄ N ₃ 0, 363.1 ; m/z found, 364.2 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.59 (d, J = 2.0 Hz, 1 H), 8.1 1 (s, 1 H), 7.60 (d, J = 3.3 Hz, 1 H), 7.56 - 7.48 (m, 2H), 6.68 (dd, J = 3.3, 0.9 Hz, 1 H), 5.51 - 5.29 (m, 1 H), 5.07 (d, J = 3.5 Hz, 2H), 4.64 - 4.48 (m, 1 H), 4.42 - 4.27 (m, 2H), 4, 16 - 4.02 (m, 1 H). -[6-(5-Chioro-2-thienyl)pyrroloi3,2-b]pyridin-1 -yll-1 -(3

The title compound was prepared in a manner analogous to Example 130. MS (ESI): mass calcd. for Ci ₆ Hi ₃ C!FN ₃ OS, 349.0; m/z found, 350.0 [i /!+H] ^÷ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.06 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 7.43 (d, J = 3.9 Hz, 1 H), 7.20 (d, J = 3.9 Hz, 1 H), 6.61 (dd, J = 3.4, 0.8 Hz, 1 H), 5.59 - 5.35 (m, 1 H), 5.06 (s, 2H), 4.65 - 4.47 (m, 1 H), 4.40 - 4.16 (m, 2H), 4.07 - 3.88 (m, 1 H).

Example 373: 1 -(Azetidin-1 -yl)-2-r6-(5-chloro-2-thienyl)pyrrolor3,2-blpyridin-1 yljethanone.

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for Ci ₆ H ₁₄ CIN ₃ OS, 331 .1 ; m/z found, 332.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.61 (d, J = 2.0 Hz, 1 H), 8.06 (dd, J = 2.1 , 0.8 Hz, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 7.44 (d, J = 3.9 Hz, 1 H), 7.20 (d, J = 3.9 Hz, 1 H), 6.60 (dd, J = 3.3, 0.8 Hz, 1 H), 4.99 (s, 2H), 4.23 (t, J = 7.7 Hz, 2H), 3.92 (t, J = 7.7 Hz, 2H), 2.34 - 2.22 (m, 2H). -[3-Chloro-6-(2.3,4-trifluorophenvnpyrrolof3.2-blpyridin-1 -yll-

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for C18H12CIF4N3O, 397,1 ; m/z found, 398,0 [M+Hf. H NMR (300 MHz, DMSO-d ₆ ) δ 8.58 (s, 1 H), 8, 17 (s, 1 H), 7,86 (s, 1 H), 7.58 - 7.43 (m, 2H), 5.62 - 5.31 (m, 1 H), 5.07 (s, 2H), 4.68 - 4.47 (m, 1 H), 4.46 - 4.14 (m, 2H), 4.07 - 3.88 (m, 1 H).

Example 375: N.N-Dimethyl-2-i6-(3,4,5-trifluorophenvnpyrroloi3,2-blpyridi n-1 -

Step A: 2-(6-Bromo-1 H-pyrrQio[3,2-b]pyridin-1 -yl)-N,ISj-dimethviacetamide. The title compound was prepared in a manner analogous to Intermediate 10, using 6-bromo-1 H-pyrroio[3,2~b]pyridine and 2-bromo-N,IM~

dimethylacetarnide, MS (ESI): mass calcd. for CnHi ₂ BrN ₃ 0, 281 .1 ; m/z found, 282.0 [M+Hf.

Step B: N.jM-dimethyl-2-i6-i3,4,5-trifluorophenyl pyrroloi3,2-b1pyridin-1 - yllacetamide. The title compound was prepared in a manner analogous to Example 1 , Step A, using 2-(6-bromo-1 H-pyrrolo[3,2-b]pyridin-1 -yl)-N,N- dimethylacetamide and (3,4,5-trifluorophenyl)boronic acid. MS (ESI): mass calcd. for Ci H-uFaNsO, 333.1 ; m/z found, 334.1 [M+H] ^{+ 1} H NMR (500 MHz, CD ₃ OD) δ 8.55 (d, J = 2.0 Hz, 1 H), 8.07 (dd, J = 2.0, 0.9 Hz, 1 H), 7.55 (d, J = 3.3 Hz, 1 H), 7.53 - 7.46 (m, 2H), 6.66 (dd, J = 3.3, 0.9 Hz, 1 H), 5.25 (s, 2H), 3.20 (s, 3H), 2.98 (s, 3H).

The title compound was prepared in a manner analogous to Example 375, MS (ES!): mass calcd. for C ₇ H ₁₅ F2N ₃ 0, 315.1 ; m/z found, 316.1 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.58 (d, J = 1 .9 Hz, 1 H), 8.09 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.56 (d, J = 3.3 Hz, 1 H), 7.37 - 7,29 (m, 2H), 6,97 - 6.90 (m, 1 H), 6.66 (dd, J = 3.4, 0.9 Hz, 1 H), 5.26 (s, 2H), 3.19 (s, 3H), 2.98 (s, 3H). -f6-f3-(Difluoromethyl)phenyllpyrrolof3,2-blpyridin-1 -yll-N,N-

The title compound was prepared in a manner analogous to Example 3/5. MS (ESI): mass calcd. for Ci ₈ Hi ₇ F ₂ N ₃ 0, 329.1 ; m/z found, 330.1 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.58 (d, J = 1 .9 Hz, 1 H), 8.06 (dd, J = 2.0, 0.9 Hz, 1 H), 7.87 - 7.77 (m, 2H), 7.61 - 7.50 (m, 3H), 6.84 (t, J = 56.2 Hz, 1 H), 6.66 (dd, J = 3.3, 0.9 Hz, 1 H), 5.24 (s, 2H), 3.17 (s, 3H), 2.96 (s, 3H).

The title compound was prepared in a manner analogous to Example 375, MS (ES!): mass calcd. for 0ι ₅ Ηι ₄ 0!Ν ₃ 08, 319.1 ; m/z found, 320.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.52 (d, J = 1 .9 Hz, 1 H), 7.99 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.53 (d, J = 3.3 Hz, 1 H), 7.27 (d, J = 3.9 Hz, 1 H), 7.00 (d, J = 3.9 Hz, 1 H), 6.64 (dd, J = 3.4, 0.9 Hz, 1 H), 5.25 (s, 2H), 3.20 (s, 3H), 2.98 (s, 3H).

Example 379: 2-[6-(3,4-Difluorophenyl)pyrrolof3,2-blpyridin-1 -yll-N,N- dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for C17H15F2N3O, 315.1 ; m/z found, 316.1 [M+H] ⁺ . ¹ H NMR (500 MHz, CD3OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 8.05 (dd, J = 2.0, 0.9 Hz, 1 H), 7.64 (ddd, J = 1 1 .9, 7.7, 2.3 Hz, 1 H), 7.54 (d, J = 3.3 Hz, 1 H), 7.53 - 7.47 (m, 1 H), 7.40 - 7.32 (m, 1 H), 6.66 (dd, J = 3.3, 0.9 Hz, 1 H), 5.27 (s, 2H), 3.20 (s, 3H), 2.98 (s, 3H).

The title compound was prepared in a manner analogous to Example 130. MS (ESI): mass calcd. for C ₇ H ₁₇ N ₃ OS, 31 1 .1 ; m/z found, 312.0 [M+H] ⁺ . Ή NMR (400 MHz, DMSO-de) δ 8.59 (d, J = 2.0 Hz, 1 H), 7.98 (d, J = 1 .7 Hz, 1 H), 7.57 (d, J = 3.3 Hz, 1 H), 7.34 (d, J = 3.5 Hz, 1 H), 6.86 (dd, J = 3.5, 1 .3 Hz, 1 H), 6.57 (d, J = 2.9 Hz, 1 H), 4.98 (s, 2H), 4.21 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.8 Hz, 2H), 2.49 (s, 3H), 2.39 - 2.17 (m, 2H). -(Azetidin-1 -yl)-2-f3-chloro-6-(5-chloro-2-thienyl)pyrrolor3.2-

The title compound was prepared in a manner analogous to Example 29. S (ESI): mass calcd. for C16H13CI2N3OS, 385.0; m/z found, 385.8 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-d ₆ ) δ 8.69 (d, J = 1 .9 Hz, 1 H), 8.16 (d, J = 2.0 Hz, 1 H), 7.80 (s, 1 H), 7.49 (d, J = 4.0 Hz, 1 H), 7.22 (d, J = 3.9 Hz, 1 H), 4.99 (s, 2H), 4.25 (t, J = 7.6 Hz, 2H), 3.92 (t, J = 7.7 Hz, 2H), 2.34 - 2.25 (m, 2H). -(Azetidin-1 -yl)-2-f6-(3,4-difluorophenyl)-3-fluoro-pyrrolof3.2-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C18H14F3N3O, 345.1 ; m/z found, 346.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-de) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.28 - 8.22 (m, 1 H), 7.89 (ddd, J = 12.4, 7.8, 2.2 Hz, 1 H), 7.71 - 7.53 (m, 3H), 4.95 (s, 2H), 4.22 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.32 - 2.21 (m, 2H).

Exam le 383: 1 -(Azetidin-1 -yl)-2-i3-fluoro-6-(3,4,5-trifluorophenvnpyrroloi3,2-

The title compound was prepared in a manner analogous to Example 182, MS (ES!): mass calcd. for 363.1 ; m/z found, 364.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-ds) δ 8.77 (d, J = 1 .9 Hz, 1 H), 8.33 - 8.27 (m, 1 H), 7.86 - 7.79 (m, 2H), 7.70 (d, J = 2,2 Hz, 1 H), 4,95 (s, 2H), 4,22 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.34 - 2.23 (m, 2H).

Example 384: 2-i3-Chloro-6-(4-fiuorophenyi)pyrroloi3,2-b]pyridin-1 -yll-1 -

The title compound was prepared in a manner analogous to Example 1 . MS (ESI): mass calcd. for deH-uCIF^O, 328.1 ; m/z found, 328.9 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.72 (d, J = 1 ,9 Hz, 1 H), 8,22 (d, J = 2.0 Hz, 1 H), 7.87 - 7.74 (m, 3H), 7,35 (t, J = 8.9 Hz, 2H), 5.49 (s, 2H), 2.19 - 2.08 (m, 1 H), 1 .07 - 0.89 (m, 4H).

Example 385: 1 -(Azetidin-1 -yl)-2-r6-(3-thienyl)pyrrolof3,2-blpyridin-1 - yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for C16H15N3OS, 297.1 ; m/z found, 298.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 9,04 (d, J = 1 .7 Hz, 1 H), 8,88 (s, 1 H), 8.17 - 8.1 1 (m, 1 H), 8.03 (d, J = 3.3 Hz, 1 H), 7,80 (dd, J = 5.0, 2.9 Hz, 1 H), 7.76 (dd, J = 5.0, 1 .4 Hz, 1 H), 6.82 (dd, J = 3.2, 0.9 Hz, 1 H), 5.18 (s, 2H), 4.29 (t, J = 7.7 Hz, 2H), 3.94 (t, J = 7.7 Hz, 2H), 2.37 - 2.28 (m, 2H), -Dimethyl-2-f6-(5-methyl-2-thienvnpyrrolof3,2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 375 substituting 4,4,5,5-tetramethyl-2-(5-methylthiophen-2-yl)-1 ,3,2-dioxaborolane for (3,4,5-trifluorophenyl)boronic acid. MS (ESI): mass calcd. for Ci ₆ H ₁₇ N ₃ GS, 299.1 ; m/z found, 300.0 [M+H] ⁺ . Analytical HPLC was obtained on a Agilent 1 100 Series using an !nertsii ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C). f¾ = 0.79 min at 254 nm.

Example 387: 2-i3-Fiuoro-6-(2-thienyr¾pyrrolor3,2-b1pyndin-1 -yl]-N,N-

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for Ci5Hi ₄ FN ₃ OS, 303.1 ; m/z found, 304.0 [M+H] ⁺ . H IMMR (400 MHz, DMSO) 6 8.69 (d, J = 1 .8 Hz, 1 H), 8.14 (t, 1 H), 7,61 - 7.57 (m, 3H), 7.21 - 7.16 (m, 1 H), 5,20 (s, 2H), 3.10 (s, 3H), 2.86 (s, 3H).

Example 388: 2-[6-(5-Ethyl-2-thienyl)pyrrolo[3.2-blpyridin-1 -yll-N.N-dimethyl- acetamide trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 375, MS (ES!): mass calcd. for C17H19N3OS, 313.1 ; m/z found, 314.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ds) δ 8.76 (s, 1 H), 8.37 (br. s, 1 H), 7.81 - 7.78 (m, 1 H), 7.45 (d, J = 3.6 Hz, 1 H), 6.93 (d, J = 3,7 Hz, 1 H), 6,71 - 6,65 (m, 1 H), 5.34 (s, 2H), 3.12 (s, 3H), 2.87 (d, J = 6.1 Hz, 5H), 1.29 (t, J = 7.5 Hz, 3H).

Example 389: 1 -(Azetidin-1 -yl)-2-f3-fluoro-6-(2-thienyl)pyrrolof3,2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 182, MS (ES!): mass calcd. for C ₆ H ₁₄ FN ₃ OS, 315.1 ; m/z found, 316.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-d ₆ ) δ 8.71 (d, J = 1 .9 Hz, 1 H), 8.15 (t, J = 2,2 Hz, 1 H), 7,65 (d, J = 2.2 Hz, 1 H), 7.63 - 7,59 (m, 2H), 7.22 - 7.15 (m, 1 H), 4.95 (s, 2H), 4.23 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.35 - 2.22 (m, 2H). -i3-Fluoro-8-(5-methyl-2-thienyl)pyrroloi3,2-blpyridin-1 -yll-

The title compound was prepared in a manner analogous to Example 92 substituting 4,4,5,5-tetramethyl-2-(5-methylthiophen-2-yl)-1 ,3,2-dioxaborolane for (4-fluoro~3-methylphenyl)boronic acid. MS (ES!): mass calcd. for

Ci6Hi ₆ FN ₃ OS, 317.1 ; m/z found, 318.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-efe) δ 8.69 (d, J = 1 .9 Hz, 1 H), 8.21 (t, J = 2.2 Hz, 1 H), 7.65 (d, J = 2.2 Hz, 1 H), 7.64 - 7.60 (m, 2H), 5.20 (s, 2H), 3.10 (s, 3H), 2.86 (s, 3H), 2.07 (s, 3H). -[6-(4-Chloro-2-thienyl)pyrrolof3,2-blpyridin-1 -yll-N.N

The title compound was prepared in a manner analogous to Example 375 substituting 2-(4-chiorothiophen-2-yl)-4,4,5 _i 5-ietramethyl-1 ,3,2-dioxaborolane for (3,4,5~trifluorophenyl)boronic acid. MS (ESI): mass calcd. for

C15H14CIN3OS, 319.1 ; m/z found, 320.0 [M+H] ⁺ H NMR (500 MHz, DMSO- cfe) δ 8.84 (s, 1 H), 8.52 (s, 1 H), 7.85 (d, J = 3.3 Hz, 1 H), 7.68 (s, 2H), 6.73 (d, J = 3.3 Hz, 1 H), 5.36 (s, 2H), 3.13 (s, 3H), 2.88 (s, 3H).

EExxaammppllee 339922:: 11 --((AAzzeettiiddiinn--11 --yyll))--22--[[66--((55--eetthhvyll--22--tthhiieennvyll))pp yyrrrroolloo[[33,.22--bbllppyyrriiddiinn--11 --

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for Ci8H19N30S, 325.1 ; m/z found, 326.0 [M+H] ⁺ . Ή NMR (400 MHz, DMSO-d ₆ ) δ 8.79 (s, 1 H), 8.40 (s, 1 H), 7.82 (s, 1 H), 7.47 (d, J = 3.6 Hz, 1 H), 6.94 (d, J = 3.6 Hz, 1 H), 6.71 (d, J = 3.1 Hz, 1 H), 5.10 (s, 2H), 4.26 (t, J = 7.7 Hz, 2H), 3.93 (t, J = 7.6 Hz, 2H), 2.88 (q, J = 7.6 Hz, 2H), 2.36 - 2.24 (m, 2H), 1 .30 (t, J = 7.5 Hz, 3H).

-[6-(5-Ethyl-2-thienyl)-3-fluoro-pyrrolo[3,2-blpyridin-1 -vn-N,N-

The title compound was prepared in a manner analogous to Example 92. MS (ESi): mass calcd. for C17H18FN3OS, 331 .1 ; m/z found, 332.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-C ) δ 8.64 (d, J = 1 .8 Hz, 1 H), 8.08 (s, 1 H), 7.58 (d, J = 2.2 Hz, 1 H), 7.39 (d, J = 3.6 Hz, 1 H), 6.90 (d, J = 3.5 Hz, 1 H), 5.18 (s, 2H), 3.10 (s, 3H), 2.91 - 2.80 (m, 5H), 1 .28 (t, J = 7.5 Hz, 3H).

yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 102 substituting 2-(4-chlorothiophen-2-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane for (5-(trifluoromethyl)pyridin-3-yl)boronic acid. MS (ESI): mass calcd. for C 6Hi4C!N ₃ OS, 331 .1 ; m/z found, 332.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO- ofe) δ 8.08 (d, J = 1 .7 Hz, 1 H), 8.00 - 7.98 (m, 1 H), 7.22 (d, J = 3.3 Hz, 1 H), 6.80 (d, J = 1 .5 Hz, 1 H), 6.68 (d, J = 1 .5 Hz, 1 H), 6.08 (dd, J = 3.5, 1 .0 Hz, 1 H), 4.42 (s, 2H), 3.61 (t, J = 7.7 Hz, 2H), 3.29 (t, J = 7.8 Hz, 2H), 1 .69 - 1 .59 (m, 2H). -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(2-thienyl)pyrroloi3,

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C16H13F2N3OS, 333.1; m/z found, 334.0 [M+H] ⁺ . ¹ H

MR (500 MHz, DMSO-d ₆ ) δ 8.72 (d, J = 1.9 Hz, 1H), 8.17 (t, J =2.1 Hz, 1H), 7.66 (d, J = 2.2 Hz, 1 H), 7.64 - 7.57 (m, 2H), 7.19 (dd, J = 5.1 , 3.6 Hz, 1 H), 5.56-5.38 (m, 1H), 5.02 (d, J = 2.8 Hz, 2H), 4.65-4.50 (m, 1H), 4.41 -4.18 (m, 2H), 4.05-3.92 (m, 1H).

The title compound was prepared in a manner analogous to Example 182 substituting 2~(4~chiorothiophen~2-yl)~4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane for (5-ch!orothiophen-2-yl)boronic acid. MS (ESI): mass calcd. for

C15H13CIFN3OS, 337.0; m/z found, 338.0 [M+H] ⁺ H HMR (500 MHz, DMSO- cfe) δ 8.62 (d, J = 1.9 Hz, 1 H), 8.05 (t, J = 2.2 Hz, 1 H), 7.58 (d, J = 2,2 Hz, 1 H), 7.37 (d, J = 3.5 Hz, 1H), 6.86 (dd, J = 3.6, 1.2 Hz, 1H), 5.18 (s, 2H), 3.10 (s, 3H), 2.86 (s, 3H). -(Azetidin-1 -yl)-2-r6-(4-chloro-2-thienyl)-3-fluoro-pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 182 substituting 2-(4-cblorothiophen-2-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane for (5~chlorothiophen~2-yl)boronic acid. MS (ESI): mass calcd. for

C ₆ Hi ₃ CiFN ₃ OS, 349,0; m/z found, 350,0 [M+H] ⁺ . H NMR (500 MHz, DMSO- cfe) 5 8.71 (d, J = 1 .8 Hz, 1 H), 8.21 (t, J = 2.1 Hz, 1 H), 7.68 (d, J = 2.2 Hz, 1 H), 7.64 (s, 2H), 4.95 (s, 2H), 4.23 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.33 - 2.24 (m, 2H),

Example 398: 2-i6-(5-Ethyl-2-thienyl)-3-fiuoro-pyrrolo[3,2-b]pyridin-1 -yll-1 ~(3- fluoroazetidin-1 -yl)ethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd, for Ci ₈ H ₁₇ F ₂ N ₃ OS, 361 .1 ; m/z found, 362.0 [M+H] ⁺ .

Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsii ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACN in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 mL/min (Temperature = 50 °C), R _t = 1 .14 min at 254 nm. Example 399: 1 -(Azetidin-1 -yl)-2-r6-(2-thienyl)pyrrolof3,2-blpyridin-1

The title compound was prepared in a manner analogous to Example 102. MS (ESi): mass calcd. for C ₆ H ₁₅ !M ₃ OS, 297.1 ; m/z found, 298.0 [M+H] ⁺ . Ή N!VfR (400 MHz, CD3OD) δ 8.63 (d, J = 1 .9 Hz, 1 H), 8.08 - 8.05 (m, 1 H), 7.55 (d, J = 3.3 Hz, 1 H), 7.48 (dd, J = 3.6, 1 .2 Hz, 1 H), 7.43 (dd, J = 5.1 , 1 .2 Hz, 1 H), 7.14 (dd, J = 5.2, 3.6 Hz, 1 H), 6.68 - 6.62 (m, 1 H), 5.00 (s, 2H), 4.27 (t, J = 7.7 Hz, 2H), 4.07 (t, J = 7.7 Hz, 2H), 2.43 - 2.31 (m, 2H),

Example 400: N.N-Dimethyl-2-i6-(2-thienvnpyrrolo[3,2-b]pyridin-1

yilacetamide.

The title compound was prepared in a manner analogous to Example 3/5. MS (ESI): mass calcd. for C15H ₁ 5N3OS, 285.1 ; m/z found, 286.0 [ H-H] ^{÷ 1} H NMR (500 MHz, CD3OD) δ 8.61 (d, J = 1 .9 Hz, 1 H), 8.08 - 8.02 (m, 1 H), 7.51 (d, J = 3.3 Hz, 1 H), 7.46 (dd, J = 3.6, 1 .1 Hz, 1 H), 7.42 (dd, J = 5.1 , 1 .1 Hz, 1 H), 7.13 (dd, J = 5.1 , 3.6 Hz, 1 H), 6.64 (dd, J = 3.3, 0.9 Hz, 1 H), 5.26 (s, 2H), 3.21 (s, 3H), 2.99 (s, 3H).

-(Azetidin-1 -yl)-2-[6-(5-ethyl-2-thienyl)-3-fluoro-pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for Ci8Hi ₈ FN ₃ OS, 343, 1 ; m/z found, 344,0 [M+H] ⁺ . H NMR (400 MHz, CD3OD) δ 8.60 (d, J = 1 .8 Hz, 1 H), 8.01 (t, J = 2.1 Hz, 1 H), 7.44 (d, J = 2.4 Hz, 1 H), 7.30 (d, J = 3.6 Hz, 1 H), 6.87 - 6.83 (m, 1 H), 4.92 (s, 2H), 4.34 - 4.26 (m, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2,94 - 2,84 (m, 2H), 2.44 - 2.33 (m, 2H), 1 .35 (t, J = 7.5 Hz, 3H).

Example 402: 1 -(3-Fluoroazetidin-1 -yl)-2-f3-fluoro-6-(5-methyl-2- thienyl)pyrrolor3.2-blpyridin-1 -yllethanone trifluoroacetate salt.

The title compound was prepared in a manner analogous to Example 182 substituting 4,4,5,5-tetramethyl-2-(5-methylthiophen-2-yl)-1 ,3,2-dioxaboroiane for (5-chiorothiophen-2-yl)boronic acid. MS (ESI): mass calcd. for

Ci7Hi5F ₂ N30S, 347.1 ; m/z found, 348.0 [M+H] ⁺ . ¹ H NMR (400 MHz, CD ₃ OD) δ 8.71 (s, 1 H), 8.34 (s, 1 H), 7.67 (d, J = 2.2 Hz, 1 H), 7.36 (d, J = 3.6 Hz, 1 H), 6.85 (d, J = 3.6 Hz, 1 H), 5.54 - 5,31 (m, 1 H), 5.08 (d, J = 3.1 Hz, 2H), 4.71 - 4.55 (m, 1 H), 4.49 - 4.28 (m, 2H), 4.19 - 4.02 (m, 1 H), 2.54 (s, 3H). Example 403: 1 -(Azetidin-1 -yl)-2-r6-(3-chloro-2-thienyl)pyrrolo[3,2-blpyridin- lethar

The title compound was prepared in a manner analogous to Example 102. MS (ESi): mass calcd. for C ₆ H ₁₄ C1N ₃ 0S, 331 .1 ; m/z found, 332.0 [M+H] ⁺ . ^! H NMR (500 MHz, CD ₃ OD) δ 8.56 (d, J = 1 .8 Hz, 1 H), 8.08 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 7.55 (d, J = 5.4 Hz, 1 H), 7.1 1 (d, J = 5.4 Hz, 1 H), 6.69 (dd, J = 3.3, 0.9 Hz, 1 H), 5.00 (s, 2H), 4.31 - 4.24 (m, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.41 - 2.31 (m, 2H).

Example 404: 1 -(Azetidin-1 -yl)-2-[6-(2-methylthiazol-5-yl)pyrrolo[3,2' b]pyridin-1 -yilethanone.

The title compound was prepared in a manner analogous to Example 102 substituting 2-methyl-5-(4,4 _! 5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)thiazole for (5-(trifiuoromethyi)pyridin-3-yl)boronic acid. MS (ESI): mass calcd. for

Ci6H ₁₆ N ₄ OS, 312.1 ; m/z found, 313.0 [M+H] ^{+ 1} H NMR (500 MHz, CD ₃ OD) δ 8.56 (d, J = 1 .9 Hz, 1 H), 8.08 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.97 (s, 1 H), 7.58 (d, J = 3.3 Hz, 1 H), 6.67 (dd, J = 3.3, 0.9 Hz, 1 H), 5.01 (s, 2H), 4.32 - 4.25 (m, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.75 (s, 3H), 2.43 - 2.34 (m, 2H). -(Azetidin-1 -yl)-2-(6-thiazol-5-ylpyrrolor3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 102 substituting 5-(4,4,5,5-tetramethyl-1 ,3,2~dioxaborolan-2-yi)thiazoie for (5- (trifluoromethyl)pyridin-3-yl)boronic acid. MS (ESI): mass calcd. for

Ci5Hi4N ₄ OS, 298.1 ; m/z found, 299.0 [M+H] ⁺ .

Example 406: 1 -(Azetidin-1 -yl)-2-[6-(6-fluoro-3-pyridyl)pyrrolo[3,2-b]pyridin-1 - yllethanone.

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for Ci ₇ H ₁₅ FN ₄ 0, 310.1 ; m/z found, 31 1 .1 [M+H] ⁺ ' H NMR (500 MHz, CD3OD) δ 8.61 (d, J = 1 .9 Hz, 1 H), 8.56 - 8.53 (m, 1 H), 8.32 - 8.27 (m, 1 H), 8.14 (dd, J = 2.0, 0.9 Hz, 1 H), 7.61 (d, J = 3.3 Hz, 1 H), 7.23 - 7.18 (m, 1 H), 6.70 (dd, J = 3,4, 0.9 Hz, 1 H), 5.03 (s, 2H), 4.32 - 4.25 (m, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.42 - 2.33 (m, 2H).

Example 407: 1 -(Azetidin-1 -yl)-2-i3-chlQro-6-(4-methyl-2-thienyl)pyrroloi3 ₁ 2-

The title compound was prepared in a manner analogous to Example 29. MS (ES!): mass calcd. for C17H16CIN3OS, 345.1 ; m/z found, 346.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 8.69 (d, J = 1 .9 Hz, 1 H), 8.14 (d, J = 1 .9 Hz, 1 H), 7.76 (s, 1 H), 7.44 (d, J = 1 .4 Hz, 1 H), 7.18 (t, J = 1 .3 Hz, 1 H), 5,00 (s, 2H), 4.25 (t, J = 7.7 Hz, 2H), 3.95 - 3.89 (m, 2H), 2.33 - 2.25 (m, 5H).

Example 408: 1 -(Azetidin- -yl)-2-f3-chloro-6-(5-ethyl-2-thienyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 29. MS (ES!): mass calcd. for C ₈ H ₁₈ C1N ₃ 0S, 359.1 ; m/z found, 360.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.64 (d, J = 1 .8 Hz, 1 H), 8.05 (d, J = 1 .9 Hz, 1 H), 7.59 (s, 1 H), 7.31 (d, J = 3.6 Hz, 1 H), 6.87 - 6.84 (m, 1 H), 4.99 (s, 2H), 4.36 - 4.29 (m, 2H), 4.08 (t, J = 7.8 Hz, 2H), 2.94 - 2.86 (m, 2H), 2.45 - 2.35 (m, 2H), 1 .35 (t, J = 7.5 Hz, 3H).

The title compound was prepared in a manner analogous to Example 29. MS (ES!): mass calcd. for C ₆ H ₁₄ C!N ₃ 0S, 331 .1 ; m/z found, 332.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-cfe) δ 8.74 (d, J = 1 .9 Hz, 1 H), 8.17 (d, J = 1 .9 Hz, 1 H), 7.78 (s, 1 H), 7.64 - 7.58 (m, 2H), 7.20 (dd, J = 5.0, 3.6 Hz, 1 H), 5.01 (s, 2H), 4.25 (t, J = 7.7 Hz, 2H), 3.92 (t, J = 7.7 Hz, 2H), 2.34 - 2.25 (m, 2H). -(Azetidin-1 -yl)-2-f3-chloro-6-(5-methyl-2-thienyl)pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 29 substituting 4,4,5,5-tetramethyl-2-(5-niethylthiophen-2-yl)-1 ,3,2-dioxaborolane for (3,4~difluorophenyl)boronic acid. MS (ESI): mass calcd. for C17H16CIN3OS, 345.1 ; m/z found, 346.0 [M+H] ⁺ . H NMR (500 MHz, CD ₃ OD) δ 8.62 (d, J = 1 .8 Hz, 1 H), 8.03 (d, J = 1 .8 Hz, 1 H), 7.59 (s, 1 H), 7.29 (d, J = 3.5 Hz, 1 H), 6.84 - 6.79 (m, 1 H), 4.98 (s, 2H), 4.37 - 4.28 (m, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.53 (d, J = 1 .1 Hz, 3H), 2.44 - 2,34 (m, 2H).

Example 41 1 : 2-r6-(4-Fluorophenyl)pyrrolof3.2-blpyridin-1 -yll-N-methyl-N-

(2,2,2-trifluoroethyDacetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C18H15F4N3O, 365.1 ; m/z found, 366.0 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.55 (d, J = 1 .9 Hz, 1 H), 8.01 - 7.99 (m, 1 H), 7.71 - 7.66 (m, 2H), 7.54 (d, J = 3.4 Hz, 1 H), 7.24 - 7.18 (m, 2H), 6.67 (dd, J = 3.3, 0.9 Hz, 1 H), 5.37 (s, 2H), 4.16 (q, J = 9.3 Hz, 2H), 3.33 (s, 3H). -[3-Chloro-6-(5-methyl-2-thienyl)pyrrolof3,2-blpyridin-1 -yll-1 -

The title compound was prepared in a manner analogous to Example 148 substituting 2-bromo-1 -(3-fiuoroazetidin-1 -yl)ethanone (Intermediate 2) for 2- bromo-N,N-dimethylacetamide and 4,4,5,5-tetramethyl-2-(5-methylthiophen- 2-yl)-1 _! 3,2-dioxaborolane for (4-fluoro-3-methyiphenyl)boronic acid. MS (ESI): mass caicd. for C17H15CIFN3OS, 363.1 ; m/z found, 364.0 [M+H] ⁺ . 'H NMR (500 MHz, CD3OD) δ 8.63 (d, J = 1 .9 Hz, 1 H), 8.05 (d, J = 1 .8 Hz, 1 H), 7.59 (s, 1 H), 7.29 (d, J = 3.5 Hz, 1 H), 6.83 - 6.80 (m, 1 H), 5.50 - 5.33 (m, 1 H),

5.04 (d, J = 3.5 Hz, 2H), 4.64 - 4,54 (m, 1 H), 4.45 - 4.30 (m, 2H), 4.16 - 4.06 (m, 1 H), 2.52 (d, J = 1 .1 Hz, 3H).

Example 413: 2-[3-Chloro-6-(5-chlQro-2-thienyl)pyrroio[3,2-b1pyridin-1 -yll-1 - (3-fluoroazetidin-1 -vnethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C16H ₁ 2CI2FN3OS, 383.0; m/z found, 384.0 [M+H] ⁺ . 'H NMR (500 MHz, CD ₃ OD) δ 8.62 (d, J = 1 .8 Hz, 1 H), 8.09 (d, J = 1 .9 Hz, 1 H), 7.63 (s, 1 H), 7.33 (d, J = 3.9 Hz, 1 H), 7.04 (d, J = 3.9 Hz, 1 H), 5.51 - 5.34 (m, 1 H), 5.05 (d, J = 4.0 Hz, 2H), 4.66 - 4.57 (m, 1 H), 4.46 - 4.31 (m, 2H), 4.16 - 4.06 (m, 1 H). -[3-Chloro-6-(4-chloro-2-thienyl)pyrrolof3,2-blpyridin-1 -yll-

The title compound was prepared in a manner analogous to Example 148 substituting 2-(4-chlorothiophen-2-yl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane for (4-fluoro-3-meihylphenyl)boronic acid. MS (ESI): mass calcd. for

Ci ₅ H ₁₃ Ci ₂ N ₃ OS, 353.0; m/z found, 354.0 [M+H] ⁺ H NMR (500 MHz, CD ₃ OD) δ 7.84 (d, J = 1 .9 Hz, 1 H), 7.33 (d, J = 1 .9 Hz, 1 H), 6.80 (s, 1 H), 6.62 (d, J = 1 .5 Hz, 1 H), 6.52 (d, J = 1 .5 Hz, 1 H), 4.46 (s, 2H), 2.39 (s, 3H), 2.17 (s, 3H).

Example 415: 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll-N- methyl-N-(2,2,2-trifluoroethyl)acetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C19H17F4N3O, 379.1 ; m/z found, 380.0 [M+H] ⁺ . H NMR (500 MHz, DMSO- fe) δ 8.61 (d, J = 2.0 Hz, 1 H), 8.05 (dd, J = 2.0, 0.9 Hz, 1 H), 7.63 (dd, J = 7.6, 2.4 Hz, 1 H), 7.57 (d, J = 3.3 Hz, 1 H), 7.57 - 7.53 (m, 1 H), 7.26 (dd, J = 9.7, 8,5 Hz, 1 H), 6,59 (dd, J = 3.3, 0.9 Hz, 1 H), 5.39 (s, 2H), 4,19 (q, J = 9.6 Hz, 2H), 3.26 (s, 3H), 2.33 (d, J = 1 .8 Hz, 3H). -[3-Chloro-6-(4-methyl-2-thienyl)pyrrolof3,2-blpyridin-1 -yll-1 -

The title compound was prepared in a manner analogous to Example 148 substituting 2-bromo-1 -(3-fiuoroazetidin-1 -yl)ethanone (Intermediate 2) for 2- bromo-N,N-dimethylacetamide and 4,4,5,5-tetramethyl-2-(4-methylthiophen- 2-yl)-1 _! 3,2-dioxaborolane for (4-fluoro-3-methylphenyl)boronic acid. MS (ESI): mass caicd. for C17H15CIFN3OS, 363.1; m/z found, 364.0 [M+H] ⁺ . 'H NMR (500 MHz, DMSO-ds) δ 8.70 (d, J = 1.9 Hz, 1H), 8.15 (d, J = 1.9 Hz, 1H), 7.77 (s, 1H), 7.43 (d, J= 1.4 Hz, 1 H), 7.18 (t, J = 1.2 Hz, 1 H), 5.56 - 5.40 (m, 1H), 5.06 (d, J = 3.2 Hz, 2H), 4.63 - 4,54 (m, 1 H), 4.40 - 4.31 (m, 1 H), 4.31 - 4.21 (m, 1H), 4.04-3.93 (m, 1H), 2.27 (d, J= 1.1 Hz, 3H).

Example 417: 2-[3-Chloro-6-(2-thienyl)pyrroloi3,2-b]pyridin-1 -yll-1 -(3- fluoroazetidin-1 -ypethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci6H ₁₃ CiFN ₃ OS, 349.0; m/z found, 350.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 9.58 (d, J = 1.9 Hz, 1 H), 9.01 (d, J = 1.9 Hz, 1 H), 8.61 (s, 1 H), 8.47 - 8.39 (m, 2H), 8.03 (dd, J = 5.1 , 3.6 Hz, 1 H), 6.40 - 6.21 (m, 1H), 5.90 (d, J = 2,9 Hz, 2H), 5.48-5.35 (m, 1H), 5.28-5.14 (m, 1H), 5.14-5.03 (m, 1H), 4.88-4.75 (m, 1H). -[3-Chloro-6-(4-chloro-2-thienyl)pyrrolo[3,2-blpyridin-1 -yll-1 ^■

The title compound was prepared in a manner analogous to Example 148 substituting 2-bromo-1 -(3-f!uoroazetidin-1 -y!)ethanone (Intermediate 2) for 2- bromo-N,N-dimethylacetamide and 2-(4-chlorothiophen-2-yl)-4, 4,5,5- tetramethyl-1 ,3,2-dioxaboro!ane for (4-fluoro-3-methylphenyl)boronic acid. MS (ESI): mass calcd. for C-ieHiaCiaFNaOS, 383.0; m/z found, 384.0 [M+H] ⁺ H NMR (500 MHz, DMSO-efe) δ 8.75 (d, J = 1 .8 Hz, 1 H), 8.24 (d, J = 1 .9 Hz, 1 H), 7.82 (s, 1 H), 7.67 - 7.61 (m, 2H), 5.59 - 5.39 (m, 1 H), 5.07 (s, 2H), 4.65 - 4.53 (m, 1 H), 4.41 - 4.31 (m, 1 H), 4.31 - 4.20 (m, 1 H), 4.04 - 3.92 (m, 1 H).

Example 419: N-Ethyl-2-[6-(4-fluorophenyl)pyrrolof3,2-blpyridin-1 -ylj-N- methyl-acetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for Ci8Hi ₈ FN ₃ 0, 31 1 .1 ; m/z found, 312.1 [M+H] ⁺ . Analytical HPLC was obtained on a Agilent 1 100 Series using an Inertsil ODS-3 column (Sum, 50 x 3 mm), mobile phase of 5-99% ACIM in 0.05% TFA over 1 .6 min and then hold at 99% ACN for 0.4 min, at a flow rate of 2.2 niL/min

(Temperature = 50 °C). F¾ = 0.82 min at 254 nm. -r3-Chloro-6-f2-thienyl)pyrrolof3.2-blpyridin-1 -vn-N.N-

The title compound was prepared in a manner analogous to Example 148. MS (ES!): mass calcd. for Ci5H ₁₄ C!N ₃ OS, 319.1 ; m/z found, 320.0 [M+H] ⁺ . ^! H NMR (500 MHz, CD ₃ OD) δ 8.68 (d, J = 1 .9 Hz, 1 H), 8.1 1 (d, J = 1 .8 Hz, 1 H), 7.58 (s, 1 H), 7.50 (dd, J = 3.6, 1 .2 Hz, 1 H), 7.45 (dd, J = 5.2, 1 .2 Hz, 1 H), 7.15 (dd, J = 5.2, 3.6 Hz, 1 H), 5.27 (s, 2H), 3.20 (s, 3H), 2.98 (s, 3H).

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci ₇ H ₁₈ ClN ₃ OS, 347.1 ; m/z found, 348.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.62 (d, J = 1 .8 Hz, 1 H), 8.03 (d, J = 1 .9 Hz, 1 H), 7.55 (s, 1 H), 7.29 (d, J = 3.6 Hz, 1 H), 6.88 - 6.81 (m, 1 H), 5.25 (s, 2H), 3.20 (s, 3H), 2.98 (s, 3H), 2.93 - 2.85 (m, 2H), 1 .35 (t, J = 7.5 Hz, 3H). -(Azetidin-1 -yl)-2-[3-chloro-6-(4-chloro-2-thienyl)pyrroloi3,2-

The title compound was prepared in a manner analogous to Example 29 substituting 2-(4-chtorothiopnen-2~yi)-4,4,5,5~tetramethyl~1 ,3,2-dioxaborolane for (3,4-difluorophenyl)boronic acid, MS (ESI): mass calcd. for

Ci ₆ Hi ₃ Ci ₂ N ₃ OS, 365.0; m/z found, 366.0 [M+H] ⁺ . H NMR (500 MHz, CD ₃ OD) δ 8,66 (d, J = 1 .8 Hz, 1 H), 8.15 (d, J = 1 .9 Hz, 1 H), 7.65 (s, 1 H), 7.45 (d, J = 1 .5 Hz, 1 H), 7.34 (d, J = 1 .5 Hz, 1 H), 5.00 (s, 2H), 4.34 (t, J = 7.7 Hz, 2H), 4.08 (t, J = 7.8 Hz, 2H), 2.44 - 2.35 (m, 2H).

Example 423: 2-r3-Chloro-6-(5-chloro-2-thienyl)pyrrolor3,2-blpyridin-1 -yll- -dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci ₅ Hi ₃ Ci ₂ N ₃ OS, 353.0; m/z found, 354.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.61 (d, J = 1 .8 Hz, 1 H), 8.07 (d, J = 1 .9 Hz, 1 H), 7.60 (s, 1 H), 7.32 (d, J = 3.9 Hz, 1 H), 7.03 (d, J = 4.0 Hz, 1 H), 5.27 (s, 2H), 3.20 (s, 3H), 2.98 (s, 3H).

Example 424: 2-f3-Chloro-6-(5-ethyl-2-thienyl)pyrrolof3,2-blpyridin-1 -yll-1 -(3- fluoroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci ₈ H _{i 7} C N ₃ OS, 377.1 ; m/z found, 378.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.64 (d, J = 1 .8 Hz, 1 H), 8.06 (d, J = 1 .8 Hz, 1 H), 7.58 (s, 1 H), 7.30 (d, J = 3.6 Hz, 1 H), 6,86 - 6,83 (m, 1 H), 5.50 - 5.33 (m, 1 H), 5.04 (d, J = 3.5 Hz, 2H), 4.65 - 4.55 (m, 1 H), 4.45 - 4.29 (m, 2H), 4, 18 4.05 (m, 1 H), 2.94 - 2.85 (m, 2H), 1 .35 (t, J = 7.5 Hz, 3H).

Example 425: 2-[6-f2-Fluoro-3-(trifluoromethyl)phenyllpyrrolof3,2-blpyrid in-1 - νΠ-Ν,Ν-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for C18H15F4N3O, 365.1 ; m/z found, 366.0 [M+H] ⁺ . H !MMR (500 MHz, CDCI3) δ 8.61 - 8.59 (m, 1 H), 7.78 - 7,74 (m, 1 H), 7.73 - 7.68 (m, 1 H), 7.64 - 7.58 (m, 1 H), 7,39 (d, J = 3.4 Hz, 1 H), 7.34 (t, J = 7.7 Hz, 1 H), 6.81 (dd, J = 3.3, 0.9 Hz, 1 H), 4.96 (s, 2H), 3.1 1 (s, 3H), 3.00 (s, 3H).

Example 426: 2-[6-(5-Cbloro-4-methyl-2-thienyl)pyrroloi3,2-b]pyridin-1 -yll- N.N-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 375 substituting 2~(5~chloro~4-methylthiophen~2-yl)~4,4,5,5-tetramethyl-1 ,3,2- dioxaborolane for (3,4,5-trifluorophenyl)boronic acid. MS (ESI): mass calcd. for C ₆ Hi ₆ CIN ₃ OS, 333.1 ; m/z found, 334.0 [M+H] ⁺ . Ή NMR (500 MHz, CDCI3) δ 8.64 (d, J = 2.0 Hz, 1 H), 7.58 (s, 1 H), 7.32 (d, J = 3,4 Hz, 1 H), 7,01 (s, 1 H), 6.76 (d, J = 3.3 Hz, 1 H), 4.92 (s, 2H), 3.1 1 (s, 3H), 3.01 (s, 3H), 2.22 (s, 3H). Example 427: 2-r6-(2.5-Dimethyl-3-thienyl)pyrrolof3,2-blpyridin-1 -vn-N,N-

The title compound was prepared in a manner analogous to Example 375. S (ESI): mass calcd. for C ₇ H ₁₉ N ₃ OS, 313.1 ; m/z found, 314.1 [M+H] ⁺ . Ή NMR (500 MHz, CDCIs) δ 8.49 (d, J = 1 .8 Hz, 1 H), 7.51 (s, 1 H), 7.32 (d, J = 3.4 Hz, 1 H), 6.76 (dd, J = 3.3, 0.9 Hz, 1 H), 6.73 (s, 1 H), 4.91 (s, 2H), 3.07 (s, 3H), 2.99 (s, 3H), 2.46 (s, 3H), 2.44 (s, 3H). Example 428: N.N-Dimethyl-2-f6-(2.4,5-trimethyl-3-thienyl)pyrrolof3.2- blpyridin-1 -yilacetamide.

The title compound was prepared in a manner analogous to Example 375 substituting 4,4,5,5-tetramethyl-2-(2,4,5-trimethylthiophen-3-yl)-1 ,3,2- dioxaborolane for (3,4,5-trifluorophenyl)boronic acid. MS (ESI): mass calcd. for C isHa NsOS, 327.1 ; m/z found, 328.1 [M+H] ⁺ ' H NMR (500 MHz, CDCi ₃ ) 8.32 (d, J = 1 .7 Hz, 1 H), 7.41 - 7.38 (m, 1 H), 7.35 (d, J = 3.3 Hz, 1 H), 6.78 (dd, J = 3.3, 0.9 Hz, 1 H), 4.90 (s, 2H), 3.06 (s, 3H), 2.98 (s, 3H), 2.35 (s, 3H), 2.26 (s, 3H), 1 .92 (s, 3H).

Example 429: 2-r6-(3-Chlorophenyl)pyrrolor3,2-blpyridin-1 -yll-N.N-dimethy acetamide.

The title compound was prepared in a manner analogous to Example 375, MS (ES!): mass calcd. for Ci ₇ Hi ₆ C!N ₃ 0, 313.1 ; m/z found, 314.1 [M+H] ⁺ . ¹ H NMR (500 MHz, CDCI ₃ ) δ 8.67 (s, 1 H), 7.86 (dd, J = 2.0, 0.9 Hz, 1 H), 7.59 (t, J = 1 .9 Hz, 1 H), 7.52 - 7.46 (m, 1 H), 7,38 (t, J = 7.8 Hz, 1 H), 7.35 - 7.31 (m, 2H), 6.78 (dd, J = 3.4, 0.9 Hz, 1 H), 4.94 (s, 2H), 3.10 (s, 3H), 3.00 (s, 3H).

Example 430: 2-[6-(4-Fluorophenyl)pyrrolof3,2-blpyridin-1 -yll-N,N-dimethyl- aceiamide.

The title compound was prepared in a manner analogous to Example 375, MS (ES!): mass calcd. for Ci ₇ Hi ₆ FN ₃ 0, 297.1 ; m/z found, 298.0 [M+H] ^÷ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.10 - 8.08 (m, 1 H), 7.80 - 7.74 (m, 2H), 7.57 (d, J = 3,3 Hz, 1 H), 7,36 - 7.30 (m, 2H), 6.58 (dd, J = 3,3, 0.8 Hz, 1 H), 5.25 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H).

Example 431 : 2-[6-(2-Fluorophenyl)pyrrolof3,2-blpyridin-1 -yll-N,N-dimethyl acetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ES!): mass calcd. for C ₇ H ₁₆ FN ₃ 0, 297.1 ; m/z found, 298.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.49 (t, J = 2.0 Hz, 1 H), 8,00 (s, 1 H), 7,60 (d, J = 3,3 Hz, 1 H), 7.58 (dd, J = 8, 1 , 1 .8 Hz, 1 H), 7.47 - 7.41 (m, 1 H), 7.38 - 7.31 (m, 2H), 6.61 (dd, J = 3.3, 0.9 Hz, 1 H), 5.25 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H). -[6-(2-Fluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll

The title compound was prepared in a manner analogous to Example 375. S (ESI): mass calcd. for C ₈ Hi ₈ FN ₃ G, 31 1 .1 ; m/z found, 312.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-efe) δ 8.46 (t, J = 1 .9 Hz, 1 H), 7.97 (s, 1 H), 7.59 (d, J = 3.3 Hz, 1 H), 7.40 - 7.34 (m, 1 H), 7.34 - 7.29 (m, 1 H), 7.21 (t, J = 7.5 Hz, 1 H), 6.80 (dd, J = 3.3, 0.9 Hz, 1 H), 5.24 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H), 2.32 (d, J = 2.1 Hz, 3H).

Example 433: ISj,IM-Dimethyl-2-(6-phenylpyrrolo[3,2-b]pyridin-1 -yl)acetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for C ₇ H ₁₇ N ₃ 0, 279.1 ; m/z found, 280.1 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-efe) δ 8.64 (d, J = 2.0 Hz, 1 H), 8.1 1 - 8.09 (m, 1 H), 7.76 - 7.72 (m, 2H), 7.56 (d, J = 3.2 Hz, 1 H), 7.50 (t, J = 7.7 Hz, 2H), 7.40 - 7.35 (m, 1 H), 6.58 (dd, J = 3.2, 0.9 Hz, 1 H), 5.26 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H).

Example 434: N.N-Dimethyl-2-i6-(m-tolyl)pyrroloi3,2-blpyridin-1 -ynacetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for Ci ₈ H ₁₉ N ₃ 0, 293.2; m/z found, 294.1 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-efe) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.07 (dd, J = 2.0, 0.9 Hz, 1 H), 7.57 - 7.54 (m, 2H), 7.54 - 7.50 (m, 1 H), 7.38 (t, J = 7.6 Hz, 1 H), 7.21 - 7.16 (m, 1 H), 6,57 (dd, J = 3.3, 0.9 Hz, 1 H), 5.26 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H), 2.40 (s, 3H).

Example 435: N,N-Dimethyl-2-i6-i3-(trifluoromethyl)phenvnpyrroloi3,2- b]pyridin-1 -yllacetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for CieHieFsNsO, 347.1 ; m/z found, 348.0 [M+H] ⁺ . H !MMR (500 MHz, DMSO-d ₆ ) δ 8.71 (d, J = 2.0 Hz, 1 H), 8.22 (dd, J = 2.1 , 0.9 Hz, 1 H), 8.09 - 8.05 (m, 1 H), 8.05 (s, 1 H), 7.75 - 7.71 (m, 2H), 7.61 (d, J = 3,2 Hz, 1 H), 6.61 (dd, J = 3.3, 0.8 Hz, 1 H), 5.29 (s, 2H), 3.13 (s, 3H), 2.86 (s, 3H).

Example 436: 2-[6-f4-Fluoro-3-(trifluoromethyl)phenyllpyrrolor3,2-blpyrid in-1 - ν -Ν,Ν-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ES!): mass calcd. for 365.1 ; m/z found, 366.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ds) δ 8.68 (d, J = 2.0 Hz, 1 H), 8.20 (dd, J = 2.0, 0.9 Hz, 1 H), 8.14 - 8.08 (m, 1 H), 8.06 (dd, J = 6.8, 2.4 Hz, 1 H), 7.68 - 7,63 (m, 1 H), 7,61 (d, J = 3.3 Hz, 1 H), 6.61 (dd, J = 3.3, 0.8 Hz, 1 H), 5.27 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H). -Dimethyl-2-f6-(2,3,4-trifluorophenyl)pyrrolof3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 375. MS (ES!): mass calcd. for C17H14F3N3O, 333.1 ; m/z found, 334.0 [M+H] ⁺ . ^! H N!VIR (500 MHz, DMSO-C ) δ 8.48 (t, J = 2.0 Hz, 1 H), 8.03 (s, 1 H), 7.64 (d, J = 3.2 Hz, 1 H), 7.49 - 7.42 (m, 2H), 6.62 (dd, J = 3.3, 0.8 Hz, 1 H), 5.25 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H).

The title compound was prepared in a manner analogous to Example 375 substituting 4,4,5,5-tetramethyl-2-(5-(trifluoromethyl)thiophen-2-yl)-1 ,3,2- dioxaborolane for (3,4,5-trifluorophenyl)boronic acid. MS (ESI): mass calcd. for Ci ₆ Hi4F3N ₃ OS, 353.1 ; m/z found, 354.0 [M+Hf. ¹ H NMR (500 MHz,

CD3OD) δ 8.69 (d, J = 1 .9 Hz, 1 H), 8.25 (dd, J = 1 .9, 0.9 Hz, 1 H), 7.65 (d, J = 3.3 Hz, 1 H), 7.59 - 7.56 (m, 1 H), 7.54 - 7.51 (m, 1 H), 6.71 (dd, J = 3.3, 0.9 Hz, 1 H), 5.32 (s, 2H), 3.22 (s, 3H), 2.99 (s, 3H).

Example 439: 2-[6-(5-Chioro-3-thienyl)pyrrolo[3,2-b pyridin-1 -ylj-N.N- dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 375, MS (ES!): mass calcd. for C15H14CIN3OS, 319.1 ; m/z found, 320.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.60 (d, J = 1 .7 Hz, 1 H), 8.24 (dd, J = 1 .8, 0.9 Hz, 1 H), 7.72 (d, J = 3.4 Hz, 1 H), 7.43 (d, J = 5.8 Hz, 1 H), 7.24 (d, J = 5.8 Hz, 1 H), 6.74 (dd, J = 3.3, 0.9 Hz, 1 H), 5.33 (s, 2H), 3.19 (s, 3H), 2.97 (s, 3H).

Example 440: 2-[6-(2,5-Dichloro-3-thienyl)pyrrolof3,2-blpyridin-1 -yl1-N,N-

The title compound was prepared in a manner analogous to Example 3/5. MS (ESI): mass calcd. for C15H13G2N3OS, 353.0; m/z found, 354.0 [M+H] ⁺ , ¹ H NMR (500 MHz, CD ₃ OD) δ 8.51 (d, J = 1 .8 Hz, 1 H), 7.99 - 7.96 (m, 1 H), 7.58 (d, J = 3.3 Hz, 1 H), 7.19 (s, 1 H), 6.67 (dd, J = 3.3, 0.9 Hz, 1 H), 5.25 (s, 2H), 3.19 (s, 3H), 2.97 (s, 3H).

Example 441 : N,N-Dimethyl-2-[6-[6-(trifluoromethyl)-2-pyridvnpyrrolof3,2- b]pyridin~1 -yllacetamide.

The title compound was prepared in a manner analogous to Example 3/5. MS (ESI): mass calcd. for Ci ₇ H ₁₅ F ₃ N ₄ 0, 348.1 ; m/z found, 349.0 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 9.08 (d, J = 1 .9 Hz, 1 H), 8.50 (s, 1 H), 8.21 (d, J = 8.0 Hz, 1 H), 8.08 (t, J = 7.9 Hz, 1 H), 7.72 (d, J = 7.7 Hz, 1 H), 7.60 (d, J = 3.3 Hz, 1 H), 6.69 (dd, J = 3.3, 0.9 Hz, 1 H), 5.30 (s, 2H), 3.22 (s, 3H), 2.99 (s, 3H). -Dimethyl-2-f6-r2-(trifluoromethyl)-4-pyridyllpyrrolor3.2-

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass ca!cd. for C17H15F3N ₄ O, 348.1 ; m/z found, 349.1 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.79 - 8.72 (m, 2H), 8.34 (s, 1 H), 8.21 (s, 1 H), 8.06 - 8.00 (m, 1 H), 7.66 - 7.60 (m, 1 H), 6.73 - 6.68 (m, 1 H), 5.32 (s, 2H), 3.22 (s, 3H), 2.99 (s, 3H). Example 443: N.N-Dimethyl-2-i6-i5-(trifluoromethvn--3-Pvndyllpyrroloi3.2

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for C17H15F3N4O, 348.1 ; m/z found, 349.1 [M+H] ⁺ . ^! H NMR (500 MHz, CD ₃ OD) 5 9.16 (d, J = 2.2 Hz, 1 H), 8.90 - 8.84 (m, 1 H), 8.67 (d, J = 1 .9 Hz, 1 H), 8.49 - 8.46 (m, 1 H), 8.25 - 8.22 (m, 1 H), 7.60 (d, J = 3.3 Hz, 1 H), 6.70 (dd, J = 3.3, 0.9 Hz, 1 H), 5.30 (s, 2H), 3.21 (s, 3H), 2.98 (s, 3H).

Example 444: 2-[6-(2,6-Difluoro-3-methyl-phenyl)pyrrolof3,2-b]pyridin-1 -yll- -dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 375, MS (ES!): mass calcd. for Ci ₈ H _{i 7} F ₂ jM ₃ 0, 329.1 ; m/z found, 330.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.35 - 8.33 (m, 1 H), 7.93 - 7.91 (m, 1 H), 7.58 (d, J = 3.3 Hz, 1 H), 7.32 - 7.25 (m, 1 H), 7,03 - 6.98 (m, 1 H), 6.69 (dd, J = 3.4, 0.9 Hz, 1 H), 5.25 (s, 2H), 3.17 (s, 3H), 2.97 (s, 3H), 2.32 - 2.29 (m, 3H).

Example 445: 2-[6-(2-Fluoro-5-methyl-phenyl)pyrrolof3 ₁ 2-blpyndin-1 -yl1-N,N-

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for Ci ₈ H ₁₈ FN ₃ G, 31 1 .1 ; m/z found, 312.1 [M+H] ⁺ . Ή NMR (500 MHz, DMSO-d ₆ ) δ 8.47 (t, J = 2.1 Hz, 1 H), 7.97 (s, 1 H), 7.59 (d, J = 3.3 Hz, 1 H), 7.40 - 7.35 (m, 1 H), 7.25 - 7.19 (m, 2H), 6.60 (dd, J = 3.2, 0.9 Hz, 1 H), 5.25 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H), 2.36 (s, 3H).

Example 446: 1 -(Azetidin-1 -yl)-2-[6-[3-(difluoromethyl)phenyllpyrrolo[3,2- b]pyridin-1 -yilethanone.

The title compound was prepared in a manner analogous to Example 102. MS (ES!): mass calcd. for Ci ₉ H _{i 7} F ₂ jM ₃ 0, 341 .1 ; m/z found, 342.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ds) δ 8.69 (d, J = 2.0 Hz, 1 H), 8.17 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.96 - 7.91 (m, 2H), 7,69 - 7,56 (m, 3H), 7.12 (t, J = 55.8 Hz, 1 H), 6.62 (dd, J = 3.3, 0.9 Hz, 1 H), 5.03 (s, 2H), 4.21 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.30 - 2.22 (m, 2H). -[6-(2.4-Difluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -yll

The title compound was prepared in a manner analogous to Example 375. MS (ES!): mass calcd. for C18H17F2N3O, 329.1 ; m/z found, 330.0 [M+H] ⁺ . ^! H N!VIR (400 MHz, DMSO-C ) δ 8.44 (t, J = 1 .9 Hz, 1 H), 7.96 (s, 1 H), 7.60 (d, J = 3.3 Hz, 1 H), 7.48 - 7.39 (m, 1 H), 7.23 - 7.16 (m, 1 H), 6.60 (dd, J = 3.3, 0.8 Hz, 1 H), 5.24 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H), 2.26 - 2.23 (m, 3H).

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for Ci ₇ H ₁₅ CiFN ₃ 0, 331 .1 ; m/z found, 332.0 [M+H] ⁺ . Ή NMR (400 MHz, DMSO-d ₆ ) δ 8.49 (d, J = 2.0 Hz, 1 H), 8.05 (s, 1 H), 7.66 - 7.59 (m, 2H), 7.60 - 7.53 (m, 1 H), 7.36 (t, J = 7.8 Hz, 1 H), 6.62 (d, J = 2.7 Hz, 1 H), 5.26 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H).

Example 449: 2-f6-(3-Ethylphenyl)pyrrolof3,2-blpyridin-1 -yl1-N,N-dimethv acetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for C19H21 N3O, 307.2; m/z found, 308.1 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.63 (d, J = 2.0 Hz, 1 H), 8.09 - 8.04 (m, 1 H), 7.59 - 7.49 (m, 3H), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 H), 6.58 (d, J = 3.3 Hz, 1 H), 5.26 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H), 2.70 (q, J = 7.6 Hz, 2H), 1 .25 (t, J = 7.6 Hz, 3H).

Example 450: 2-i6-(3-Fluorophenyl)pyrroioi3.2-blpyridin-1 -yll-N,N-dimethyl- acetamide.

The title compound was prepared in a manner analogous to Example 375. MS (ESI): mass calcd. for 297.1 ; m/z found, 298.0 [M+H] ⁺ . ¹ H HMR (400 MHz, DMSO-cfe) δ 8.69 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.1 , 0.9 Hz, 1 H), 7.64 - 7.58 (m, 3H), 7.57 - 7.50 (m, 1 H), 7.23 - 7.16 (m, 1 H), 6.59 (dd, J = 3.3, 0.9 Hz, 1 H), 5.27 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H). Example 451 : 1 -(Azetidin-1 -yl)-2-[6-(2-fluoro-3-methyl-phenyl)pyrrolo[3,2- blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for Ci ₉ H ₁₈ FN ₃ 0, 323.1 ; m/z found, 324.0 [M+H] ⁺ . Ή NMR (500 MHz, DMSO-cfe) δ 8.48 (t, J = 1 .9 Hz, 1 H), 7.98 (s, 1 H), 7.62 (d, J = 3.2 Hz, 1 H), 7.41 - 7.37 (m, 1 H), 7.35 - 7.29 (m, 1 H), 7.22 (t, J = 7.5 Hz, 1 H), 6.61 (dd, J = 3.3, 0.9 Hz, 1 H), 4.99 (s, 2H), 4.20 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.33 (d, J = 2.1 Hz, 3H), 2.30 - 2.21 (m, 2H). -(Azetidin-1 -yl)-2-f6-(2.4-difluoro-3-methyl-phenyl)pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for 341 .1 ; m/z found, 342.1 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 8.45 (t, J = 2.0 Hz, 1 H), 7.96 (s, 1 H), 7.63 (d, J = 3.3 Hz, 1 H), 7.50 - 7.41 (m, 1 H), 7.24 - 7.17 (m, 1 H), 6.62 (dd, J = 3.3, 0.9 Hz, 1 H), 4.98 (s, 2H), 4.20 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.31 - 2.21 (m, 5H),

Example 453: 1 -(Azetidin-1 -yl)-2-[6-(3-chloro-2-fluoro-phenyl)pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 102. MS (ES!): mass calcd. for Ci ₈ Hi ₅ C N ₃ O, 343.1 ; m/z found, 344.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 8.50 (t, J = 1 .9 Hz, 1 H), 8.06 - 8.04 (m, 1 H), 7.66 (d, J = 3.3 Hz, 1 H), 7.65 - 7,61 (m, 1 H), 7.60 - 7.55 (m, 1 H), 7.40 - 7.34 (m, 1 H), 6.64 (dd, J = 3.3, 0.9 Hz, 1 H), 5.00 (s, 2H), 4.21 (t, J = 7.6 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.30 - 2.22 (m, 2H). -(3-Fluoroazetidin-1 -yl)-2-r6-(2-fluoro-3-methv

The title compound was prepared in a manner analogous to Example 128. MS (ESI): mass calcd. for C19H17F2N3O, 341 .1 ; m/z found, 342.1 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-cfe) δ 8,49 (t, J = 1 .9 Hz, 1 H), 8.02 (s, 1 H), 7.64 (d, J = 3.3 Hz, 1 H), 7.42 - 7.36 (m, 1 H), 7.36 - 7.29 (m, 1 H), 7.23 (t, J = 7.6 Hz, 1 H), 6.63 (dd, J = 3.2, 0.9 Hz, 1 H), 5.54 - 5.36 (m, 1 H), 5.07 (d, J = 4.7 Hz, 2H), 4.59 - 4.48 (m, 1 H), 4.36 - 4.18 (m, 2H), 4.02 - 3.90 (m, 1 H), 2.33 (d, J = 2.2 Hz, 3H).

Example 455: 1 -(3-Fluoroazetidin-1 -vn-2-f6-(2,3,4-trifluorophenyl)pyrrolo[3,2- bjjpyhdin-1 -yljethanone.

The title compound was prepared in a manner analogous to Example 128. MS (ESI): mass calcd. for C18H13F4N3O, 363.1 ; m/z found, 364.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ds) δ 8.50 (t, J = 1 .9 Hz, 1 H), 8,05 (s, 1 H), 7,67 (d, J = 3.3 Hz, 1 H), 7.51 - 7.45 (m, 2H), 6.65 (dd, J = 3.3, 0.9 Hz, 1 H), 5.54 - 5.36 (m, 1 H), 5.07 (d, J = 4.6 Hz, 2H), 4.59 - 4.49 (m, 1 H), 4.37 - 4.18 (m, 2H), 4.02 - 3.90 (m, 1 H). -(Azetidin-1 -yl)-2-f6-(3-chloro-4-fluoro-phenyl)pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for Ci ₈ Hi ₅ C!FN ₃ 0, 343.1 ; m/z found, 344.0 [M+H] ⁺ . Ή NMR (400 MHz, DMSO-cfe) δ 8.67 (d, J = 1 .9 Hz, 1 H), 8.18 - 8.15 (m, 1 H), 7.98 (dd, J = 7.2, 2.2 Hz, 1 H), 7.81 - 7.76 (m, 1 H), 7.62 (d, J = 3.4 Hz, 1 H), 7.55 (t, J = 9.0 Hz, 1 H), 6.61 (d, J = 3.3 Hz, 1 H), 5.01 (s, 2H), 4.21 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.32 - 2.21 (m, 2H).

Example 457: 1 -(3-Fluoroazetidin-1 -yl)-2-i6-(2-fluorophenvnPyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 128. MS (ESI): mass calcd. for Ci ₈ H ₁₅ F2N ₃ 0, 327.1 ; m/z found, 328.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.52 (t, J = 2.0 Hz, 1 H), 8.05 (s, 1 H), 7.65 (d, J = 3.3 Hz, 1 H), 7.64 - 7.56 (m, 1 H), 7.49 - 7.42 (m, 1 H), 7.40 - 7.32 (m, 2H), 6.64 (d, J = 3.4 Hz, 1 H), 5.55 - 5.34 (m, 1 H), 5.07 (d, J = 3.0 Hz, 2H), 4.61 - 4.46 (m, 1 H), 4.37 - 4.17 (m, 2H), 4.03 - 3.88 (m, 1 H). Example 458: 2-[6-f3-(Difluoromethvnphenyllpyrrolof3,2-blpyridin-1 -yll-1 -(3- .etidin-1-vnethar

The title compound was prepared in a manner analogous to Example 128. MS (ESi): mass calcd. for C19H16F3N3O, 359.1; m/z found, 360.0 [M+H] ⁺ . ^! H N R (400 MHz, DMSO-ds) δ 8.69 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 1.9, 0.9 Hz, 1 H), 7.95-7.91 (m, 2H), 7.69-7.62 (m, 2H), 7.62-7.57 (m, 1H), 7.12 (t, J = 55.8 Hz, 1H), 6.63 (dd, J = 3.3, 0.8 Hz, 1H), 5.56-5.36 (m, 1H), 5.10 (d, J = 2.3 Hz, 2H), 4.60 - 4.47 (m, 1 H), 4.37 - 4.18 (m, 2H), 4.04 - 3.91 (m, 1 H).

Example 459: N-Ethyl-N-methyl-2-i6-(m olv ^, l)pyrrolo[3 _l 2-b1pyridin-1 - lacetamic

The title compound was prepared in a manner analogous to Examp

(ES!): mass calcd. for C19H21N3O, 307.2; m/z found, 308.1 [M+H] ⁺ .

(3-fluoroazetidin-1-yl)ethanone.

The title compound was prepared in a manner analogous to Example 128. MS (ESI): mass calcd. for C ₉ H ₁₆ F3N ₃ 0, 359.1; m/z found, 360.0 [M+H] ⁺ . H NMR

34^"! (500 MHz, DMSO-cfe) δ 8.46 (t, J = 1 .9 Hz, 1 H), 7.99 (s, 1 H), 7.64 (d, J = 3.3 Hz, 1 H), 7.48 - 7.41 (m, 1 H), 7.24 - 7.18 (m, 1 H), 6.63 (dd, J = 3.2, 0.9 Hz, 1 H), 5.53 - 5.36 (m, 1 H), 5.06 (d, J = 4.8 Hz, 2H), 4.58 - 4.48 (m, 1 H), 4.36 - 4.19 (m, 2H), 4.01 - 3.91 (m, 1 H), 2.25 (s, 3H).

Example 461 : 2-i6-(3,4-Difluorophenyl)pyrroloi3.2-blpyridin-1 -yll-N-ethyl-N-- methyl-acetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C18H17F2N3O, 329.1 ; m/z found, 330.1 [M+H] ⁺ .

Example 462: ISj-Ethvi-N-methvi-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2- blpyridin-1 -yllacetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C ₈ Hi ₆ F3N ₃ 0, 347.1 ; m/z found, 348.0 [M+H] ⁺ .

Example 463: 1 -(Azetidin-1 -yl)-2-r6-(3-chlorophenyl)pyrrolor3.2-blpyridin-1 - yl]ethanone.

The title compound was prepared in a manner analogous to Example 102. MS (ESI): mass calcd. for Ci ₈ Hi ₆ CIN ₃ 0, 325.1 ; m/z found, 326.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-cfe) δ 8.68 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.0, 0.9 Hz, 1 H), 7.83 (t, J = 1 .9 Hz, 1 H), 7.77 - 7.72 (m, 1 H), 7.62 (d, J = 3.3 Hz, 1 H), 7.53 (t, J = 7.9 Hz, 1 H), 7.47 - 7.41 (m, 1 H), 6.61 (dd, J = 3.3, 0.9 Hz, 1 H), 5.02 (s, 2H), 4.21 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.32 - 2.21 (m, 2H). Example 464: N-Ethyl-2-[6-f2-fluoro-3-(trifluoromethyl)phenyllpyrrolo[3,2 - blpyridin-1 -yll-N-methyl-acetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for Ci ₉ H ₁₇ F ₄ N ₃ 0, 379.1 ; m/z found, 380.0 [M+H] ⁺ .

Example 465: 2-r6-f3-Chlorophenyl)pyrrolor3,2-blpyridin-1 -yll-1 -(3- fluoroazetidin-1 -ypethanone.

The title compound was prepared in a manner analogous to Example 128. MS (ESI): mass calcd. for Ci ₈ H ₁₅ CIFN ₃ 0, 343.1 ; m/z found, 344.0 [M+H] ⁺ . Ή

NMR (500 MHz, DMSO-d ₆ ) δ 8.69 (t, J = 1 .8 Hz, 1 H), 8.19 (s, 1 H), 7.82 (d, J = 1 .9 Hz, 1 H), 7.74 (d, J = 7.4 Hz, 1 H), 7.65 - 7.61 (m, 1 H), 7.56 - 7.50 (m, 1 H), 7.46 - 7.41 (m, 1 H), 6,62 (d, J = 3.0 Hz, 1 H), 5.55 - 5.37 (m, 1 H), 5.09 (s, 2H), 4.60 - 4.49 (m, 1 H), 4.36 - 4.19 (m, 2H), 4.00 - 3.91 (m, 1 H). -i6-(3-Chioro-2-fluoro-phenyl)pyrroloi3,2-b]pyridin-1 -vi]-1 -(3-

The title compound was prepared in a manner analogous to Example 128. MS (ESI): mass calcd. for C18H14CIF2N3O, 361 .1 ; m/z found, 362.0 [M+H] ⁺ H NMR (500 MHz, DMSO-d ₆ ) δ 8.69 (d, J = 2.0 Hz, 1 H), 8.20 (s, 1 H), 7.98 (dd, J = 7.1 , 2.3 Hz, 1 H), 7.81 - 7.75 (m, 1 H), 7.64 (d, J = 3.3 Hz, 1 H), 7.55 (t, J = 8.9 Hz, 1 H), 6.63 (dd, J = 3.2, 0.9 Hz, 1 H), 5.55 - 5.38 (m, 1 H), 5.08 (d, J = 2.9 Hz, 2H), 4.60 - 4.48 (m, 1 H), 4.37 - 4.19 (m, 2H), 4.02 - 3.90 (m, 1 H).

fluoroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 128. MS (ESI): mass calcd. for Ci ₈ H ₁₄ ClF ₂ N ₃ 0, 361 .1 ; m/z found, 362.0 [M+Hf. H NMR (500 MHz, DMSO-d ₆ ) δ 8.67 (d, J = 2.0 Hz, 1 H), 8.18 (dd, J = 2.2, 0.9 Hz, 1 H), 7.98 (dd, J = 7.1 , 2.3 Hz, 1 H), 7.80 - 7.75 (m, 1 H), 7.63 (d, J = 3.3 Hz, 1 H), 7.55 (t, J = 9.0 Hz, 1 H), 6.62 (dd, J = 3.3, 0.8 Hz, 1 H), 5.54 - 5.37 (m, 1 H), 5.08 (d, J = 2.8 Hz, 2H), 4.59 - 4.48 (m, 1 H), 4.36 - 4.19 (m, 2H), 4.01 - 3.90 (m, 1 H). Example 468: 2-i6-(3-Chioro-4-fluoro-phenyl)pyrroloi3,2-b]pyndin-1 -vi]-N, N-

The title compound was prepared in a manner analogous to Example 375. S (ESI): mass calcd. for C ₇ H ₁₅ CIFN ₃ G, 331 .1 ; m/z found, 332.0 [M+H] ⁺ . ¹ H

NMR (500 MHz, CD ₃ OD) δ 8.55 (d, J = 1 .9 Hz, 1 H), 8.06 (dd, J = 2.0, 0.9 Hz, 1 H), 7.83 (dd, J = 7.0, 2.3 Hz, 1 H), 7.69 - 7.62 (m, 1 H), 7.55 (d, J = 3.3 Hz, 1 H), 7.35 (t, J = 8.9 Hz, 1 H), 6.67 (dd, J = 3.3, 0,9 Hz, 1 H), 5,28 (s, 2H), 3.21 (s, 3H), 2.98 (s, 3H).

Example 469: 2-[6-(2,4-Difluoro-3-methyl-phenyl)pyrrolof3,2-blpyridin-1 -νΠ-Ν- ethyl-N-methyl-acetamide.

The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C19H19F2N3O, 343.1 ; m/z found, 344.1 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.37 - 8.33 (m, 1 H), 7.93 - 7.87 (m, 1 H), 7.59 (dd, J = 8.5, 3.3 Hz, 1 H), 7.33 - 7.24 (m, 1 H), 7.04 - 6.96 (m, 1 H), 6,73 - 6.66 (m, 1 H), 5.26 (s, 0.8H), 5.22 (s, 1 .2H), 3.54 (q, J = 7.1 Hz, 0.8H), 3.42 (q, J = 7.1 Hz, 1 .2H), 3.15 (s, 1 .8H), 2.93 (s, 1 .2H), 2.33 - 2.27 (m, 3H), 1 .26 (t, J = 7.2 Hz, 1 .2H), 1 .1 1 (t, J = 7.2 Hz, 1 .8H).

-Ethyl-N-methyl-2-r6-[3-(trifluoromethyl)phenyllpyrrolor3 .2'

The title compound was prepared in a manner analogous to Example 86. MS (ESi): mass calcd. for C ₉ H ₁₈ F ₃ N ₃ 0, 361 .1 ; m/z found, 362.1 [M+H] ⁺ . ^! H NMR (500 MHz, CD3OD) δ 8.59 - 8.57 (m, 1 H), 8.1 1 - 8.06 (m, 1 H), 7.95 (s, 1 H), 7.94 - 7.90 (m, 1 H), 7.68 - 7.63 (m, 2H), 7.56 (dd, J = 7.3, 3.3 Hz, 1 H), 6.67 (dd, J = 3.3, 0.9 Hz, 1 H), 5.26 (s, 0.8H), 5.23 (s, 1 .2H), 3.54 (q, J = 7.1 Hz, 0.8H), 3.43 (q, J = 7, 1 Hz, 1 .2H), 3.16 (s, 1 .8H), 2.94 (s, 1 .2H), 1.29 (t, J = 7.2 Hz, 1 .2H), 1.12 (t, J = 7.2 Hz, 1 .8H).

Example 471 : 1 -(Azetidin-1 -yl)-2-T3-fluoro-6-(2-fluorophenyl)pyrroloi3,2- blpyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C^H^NsO, 327.1 ; m/z found, 328.0 [M+H] ⁺ . H !MMR (400 MHz, DMSO-cfe) δ 8,54 (t, J = 1 .9 Hz, 1 H), 8.09 (s, 1 H), 7.69 (d, J = 2.2 Hz, 1 H), 7.64 - 7.57 (m, 1 H), 7.52 - 7.44 (m, 1 H), 7.41 - 7.33 (m, 2H), 4.94 (s, 2H), 4.22 (t, J = 7.6 Hz, 2H), 3.89 (t, J = 7.8 Hz, 2H), 2.32 - 2.21 (m, 2H). -(Azetidin-1 -yl)-2-f3-fluoro-6-(2-fluoro-3-methy

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C19H17F2N3O, 341 .1 ; m/z found, 342.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.51 (t, J = 1 .9 Hz, 1 H), 8.08 (s, 1 H), 7.68 (d, J = 2.2 Hz, 1 H), 7.44 - 7.31 (m, 2H), 7.23 (t, J = 7.6 Hz, 1 H), 4.94 (s, 2H), 4.21 (t, J = 7.7 Hz, 2H), 3.89 (t, J = 7.7 Hz, 2H), 2.33 (d, J = 2.2 Hz, 3H), 2.30 - 2,21 (m, 2H).

Example 473: 1 -(Azetidin-1 -yl)-2-f3-fluoro-6-(m-tolyl)pyrrolof3,2-blpyridin-1 - yllethanone.

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for Οι ₉ Ηι ₈ ΡΝ ₃ 0, 323.1 ; m/z found, 324.1 [M+H] ^{+ 1} H NMR (400 MHz, DMSO-cfe) δ 8,68 (d, J = 1 .8 Hz, 1 H), 8.16 (t, J = 2.2 Hz, 1 H), 7.63 (d, J = 2.2 Hz, 1 H), 7.60 - 7.51 (m, 2H), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.9 Hz, 1 H), 4.96 (s, 2H), 4.22 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.41 (s, 3H), 2.31 - 2.22 (m, 2H). -(Azetidin-1 -yl)-2-f6-(3,5-difluorophenyl)-3-fluoro-pyrrolor3.2-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass ca!cd. for C18H14F3N3O, 345.1 ; m/z found, 346.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.79 (d, J = 2.0 Hz, 1 H), 8.32 (t, J = 2.3 Hz, 1 H), 7.70 (d, J = 2.3 Hz, 1 H), 7.62 - 7.56 (m, 2H), 7.30 - 7.23 (m, 1 H), 4.97 (s, 2H), 4.26 - 4.19 (m, 2H), 3.94 - 3.87 (m, 2H), 2.35 - 2.24 (m, 2H), Example 475: 1 -(Azetidin-1 -yi)-2-i3-fluoro-6-i3-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C19H15F4N3O, 377.1 ; m/z found, 378.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-d ₆ ) δ 8.77 (d, J = 1 .9 Hz, 1 H), 8.31 (t, J = 2.2 Hz, 1 H), 8.12 - 8.06 (m, 2H), 7.80 - 7.74 (m, 2H), 7.70 (d, J = 2,2 Hz, 1 H), 4,99 (s, 2H), 4.22 (t, J = 7.6 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.33 - 2.21 (m, 2H).

-(Azetidin-1-yl)-2-[3-fluoro-6-[2-fluoro-3'

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C19H14F5N3O, 395.1; m/z found, 396.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.56 (t, J = 1.8 Hz, 1H), 8.19 - 8.14 (m, 1H), 7.99- 7.93 (m, 1H), 7.89-7.81 (m, 1H), 7.73 (d, J = 2.1 Hz, 1H), 7.57 (t, J = 7.8 Hz, 1 H), 4.96 (s, 2H), 4.22 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.33 - 2.21 (m, 2H),

Example 477: 1 -(Azetidin-1 -yl)-2-i3-fluoro-6-(2,3.4 rifluorophenvnPyrroloi3,2- b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for Ci ₈ H ₁₃ F ₄ N ₃ 0, 363.1; m/z found, 364.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-cfe) δ 8.54 (t, J = 1.8 Hz, 1H), 8.14- 8.10 (m, 1H), 7.73 (d, J = 2.2 Hz, 1 H), 7.52 - 7.45 (m, 2H), 4.95 (s, 2H), 4.22 (t, J = 7.7 Hz, 2H), 3.89 (t, J = 7.7 Hz, 2H), 2.30 - 2.20 (m, 2H). -(Azetidin-1 -yl)-2 6-(3-chlorophenv0-3-fluoro-pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for Ci ₈ Hi ₅ CiFN ₃ 0, 343.1 ; m/z found, 344.0 [M+H] ⁺ 'H MR (400 MHz, CD ₃ OD) δ 8.62 (d, J = 1 .8 Hz, 1 H), 8.13 (t, J = 2.1 Hz, 1 H), 7.75 (t, J = 1 .9 Hz, 1 H), 7.68 - 7.62 (m, 1 H), 7.52 - 7.45 (m, 2H), 7.44 - 7.38 (m, 1 H), 4.97 (s, 2H), 4.32 (t, J = 7,7 Hz, 2H), 4,07 (t, J = 7.8 Hz, 2H), 2.44 - 2.33 (m, 2H).

Example 479: 1 -(Azetidin-1 -yl)-2-f6-(3-chloro-2-fluoro-phenyl)-3-fluoro- pyrroio[3,2-b]pyridin-1 -vnethanone.

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C18H14CIF2N3O, 361 .1 ; m/z found, 362.0 [M+H] ⁺ H NMR (400 MHz, MeOD) δ 8.90 - 8.81 (m, 2H), 8.09 (d, J = 2.2 Hz, 1 H), 7.69 - 7.57 (m, 2H), 7.45 - 7.31 (m, 1 H), 5.20 (s, 2H), 4.41 (t, J = 7.7 Hz, 2H), 4.14 - 4.02 (m, 2H), 2.50 - 2.36 (m, 2H).

-(Azetidin-1 -yl)-2-f6-(2,4-difluoro-3-methyl-phenyl)-3-fluoro-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass ca!cd. for C19H16F3N3O, 359.1 ; m/z found, 360.0 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) 5 8.94 - 8.90 (m, 1 H), 8.87 (s, 1 H), 8.15 (d, J = 2.2 Hz, 1 H), 7.63 - 7.51 (m, 1 H), 7.20 - 7.12 (m, 1 H), 5.25 (s, 2H), 4.44 (t, J = 7.7 Hz, 2H), 4.09 (t, J = 7.8 Hz, 2H), 2.49 - 2.36 (m, 2H), 2.34 - 2.27 (m, 3H). Example 481 : 1 -(Azetidin-1 -yl)-2-i6-(3-chloro-4-fluoro-phenyl)-3-fluoro pyrrolQ[3,2-blpyridin-1 -vnethanQne.

F

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for Ci ₈ H ₁₄ CiF2N ₃ 0, 361 .1 ; m/z found, 362.0 [M+H] ⁺ . H IM MR (400 MHz, CD ₃ OD) δ 8.58 (d, J = 1 .7 Hz, 1 H), 8.14 (1, J = 2.1 Hz, 1 H), 7.81 (dd, J = 7.0, 2.3 Hz, 1 H), 7.66 - 7.59 (m, 1 H), 7.53 (d, J = 2.3 Hz, 1 H), 7.34 (t, J = 8.8 Hz, 1 H), 4.95 (s, 2H), 4.32 (t, J = 7.8 Hz, 2H), 4.06 (t, J = 7.7 Hz, 2H), 2.44 - 2.32 (m, 2H).

-(3-Fluoroazetidin-1 -yl)-2-(3-fluoro-6-phenyl-pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C18H15F2N3O, 327.1 ; m/z found, 328.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.70 (d, J = 1 .8 Hz, 1 H), 8.19 (t, J = 2.2 Hz, 1 H), 7.78 - 7.74 (m, 2H), 7.65 (d, J = 2.2 Hz, 1 H), 7.55 - 7.49 (m, 2H), 7.44 - 7.38 (m, 1 H), 5.55 - 5.37 (m, 1 H), 5.03 (d, J = 2.7 Hz, 2H), 4.61 - 4.50 (m, 1 H), 4.38 - 4.18 (m, 2H), 4.02 - 3.91 (m, 1 H).

Example 483: 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(2-fluoro-3-methyl- phenyl)pyrrolof3,2-blpyridin-1 -yl1ethanone.

The title compound was prepared in a manner analogous to Example 182. MS (ES!): mass calcd. for C ₉ H ₁₆ F ₃ N ₃ 0, 359.1 ; m/z found, 360.0 [M+H] ⁺ . ^! H NMR (500 MHz, CD3OD) δ 8.52 (t, J = 1 .8 Hz, 1 H), 8.03 (s, 1 H), 7.51 (d, J = 2.3 Hz, 1 H), 7.37 (td, J = 7.5, 1 .7 Hz, 1 H), 7.32 - 7.26 (m, 1 H), 7.19 (t, J = 7.6 Hz, 1 H), 5.47 - 5.30 (m, 1 H), 5.00 (d, J = 2.1 Hz, 2H), 4.61 - 4.50 (m, 1 H), 4.41 - 4.28 (m, 2H), 4.15 - 4.04 (m, 1 H), 2.36 (d, J = 2.3 Hz, 3H). -(3-Fluoroazetidin-1-yl)-2-r3-fluoro-6-f3-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): masscalcd. for C19H14F5N3O, 395.1; m/z found, 396.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-ofe) δ 8.77 (d, J = 1.9 Hz, 1H), 8.31 (t, J = 2.1 Hz, 1H), 8.12 - 8.05 (m, 2H), 7.80 - 7.72 (m, 2H), 7.70 (d, J = 2.1 Hz, 1 H), 5.55 - 5.37 (m, 1H), 5.09-5.00 (m, 2H), 4.62-4.50 (m, 1H), 4.40-4.17 (m, 2H), 4.04- 3.91 (m, 1H).

Example 485: 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-f2-fluoro-3'

(trifluoromethyl)phenyllpyrrolo[3,2-blpyridin-1-yl1ethano ne.

The title compound was prepared in a manner analogous to Example 182. MS

(ESi): mass calcd. for C ₁₉ H ₁₃ F ₆ N ₃ 0, 413.1; m/z found, 414.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.56 (s, 1 H), 8.18 (s, 1 H), 7.95 (t, J = 7.3 Hz, 1 H), 7.85 (t, J = 7.3 Hz, 1 H), 7.74 (s, 1 H), 7.63 - 7.52 (m, 1 H), 5.57 - 5.35 (m, 1 H), 5.03 (s, 2H), 4.64 - 4.48 (m, 1 H), 4.41 - 4.16 (m, 2H), 4.03 - 3.89 (m, 1 H). -(3-Fluoroazetidin-1-yl)-2-f3-fluoro-6-f2.3.4

The title compound was prepared in a manner analogous to Example 182. MS (ES!): mass calcd. for C18H12F5N3O, 381.1; m/z found, 382.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-ofe) δ 8.54 (t, J = 1.8 Hz, 1H), 8.13 (s, 1H), 7.73 (d, J = 2.2 Hz, 1 H), 7.53 - 7.44 (m, 2H), 5.55 - 5.35 (m, 1 H), 5.01 (d, J = 3.9 Hz, 2H), 4.62-4.49 (m, 1H), 4.39-4.17 (m, 2H), 4.01 -3.90 (m, 1H).

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C18H13F4N3O, 363.1; m/z found, 364.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.79 (d, J = 1.9 Hz, 1 H), 8.32 (t, J = 2.2 Hz, 1 H), 7.71 (d, J = 2.2 Hz, 1 H), 7.61 - 7.54 (m, 2H), 7.30 - 7.24 (m, 1 H), 5.56 - 5.38 (m, 1 H), 5.03 (d, J = 1.8 Hz, 2H), 4.61 - 4.49 (m, 1 H), 4.39 - 4.18 (m, 2H), 4.03 - 3.89 (m, 1H). -[6-(2.4-Difluoro-3-methyl-phenyl)-3-fluoro-pyrrolor3.2'

The title compound was prepared in a manner analogous to Example 182. MS (ESi): mass calcd. for C19H15F4N3O, 377.1 ; m/z found, 378.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.52 - 8.45 (m, 1 H), 8.06 (s, 1 H), 7.69 (d, J = 2.1 Hz, 1 H), 7.51 - 7.41 (m, 1 H), 7.22 (t, J = 8.7 Hz, 1 H), 5.55 - 5.36 (m, 1 H), 5.00 (d, J = 4.0 Hz, 2H), 4.61 - 4.47 (m, 1 H), 4.37 - 4.17 (m, 2H), 4.01 - 3.87 (m, 1 H), 2.25 (s, 3H).

Example 489: 2-[6-(3-Chlorophenyl)-3-fluoro-pyrrolof3,2-blpyridin-1 -yll-1 -(3- fluQroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 182. MS (ES!): mass calcd. for 0 ₈ Η ₁₄ ΟΙΡ ₂ Ν ₃ 0, 361 .1 ; m/z found, 362.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-tfe) δ 8.73 (d, J = 1 .9 Hz, 1 H), 8.26 (t, J = 2.2 Hz, 1 H), 7.84 (t, J = 1 .9 Hz, 1 H), 7.78 - 7.72 (m, 1 H), 7.68 (d, J = 2.2 Hz, 1 H), 7.54 (t, J = 7.9 Hz, 1 H), 7.50 - 7.44 (m, 1 H), 5.55 - 5.38 (m, 1 H), 5.03 (d, J = 1 .9 Hz, 2H), 4.61 - 4.50 (m, 1 H), 4,37 - 4.20 (m, 2H), 4.02 - 3.92 (m, 1 H). -i6-(3-Chioro-2-fluoro-phenyl)-3-fluoro-pyrrolo[3,2-b]pyridi r¾-1 -

The title compound was prepared in a manner analogous to Example 182. MS (ES!): masscalcd. for C18H13CIF3N3O, 379,1; m/z found, 380,0 [M+H] ⁺ . H

NMR (500 MHz, DMSO-tfe) δ 8.55 (t, J = 1.8 Hz, 1 H), 8.15 (s, 1 H), 7.72 (d, J = 2.2 Hz, 1 H), 7.68 - 7.63 (m, 1 H), 7.61 - 7.56 (m, 1 H), 7.41 - 7.34 (m, 1 H), 5.55-5.36 (m, 1H), 5.02 (d, J = 3.5 Hz, 2H), 4.61 -4.50 (m, 1H), 4.39-4,17 (m, 2H), 4.02-3.88 (m, 1H).

Example 481 : 2-[6-(3-Ethylphenyl)-3-fluoro-pyrrolor3.2-blpyridin-1 -yll-1 -(3- fluQroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 182. MS (ES!): masscalcd. for C ₂ oHi9F ₂ N ₃ 0, 355.1; m/z found, 356.1 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.69 (d, J = 1.8 Hz, 1 H), 8.16 (t, J = 2.2 Hz, 1 H), 7.64 (d, J = 2.1 Hz, 1 H), 7.59 - 7.57 (m, 1 H), 7.57 - 7.53 (m, 1 H), 7.42 (t, J = 7.6 Hz, 1 H), 7.25 (d, J = 7.6 Hz, 1 H), 5.55 - 5.37 (m, 1 H), 5.02 (d, J = 3.0 Hz, 2H), 4.61 - 4.49 (m, 1 H), 4,38 - 4.17 (m, 2H), 4.02 - 3.90 (m, 1 H), 2.71 (q, J = 7.6 Hz, 2H), 1.25 (t, J = 7.6 Hz, 3H). -(3-Fluoroazetidin-1 -yl)-2-i3-fluoro-6-(3

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C18H14F3N3O, 345.1 ; m/z found, 348.1 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.75 (d, J = 1 .9 Hz, 1 H), 8.28 (t, J = 2.2 Hz, 1 H), 7.88 (d, J = 2.2 Hz, 1 H), 7.68 - 7.80 (m, 2H), 7.59 - 7.52 (m, 1 H), 7.28 - 7.19 (m, 1 H), 5.56 - 5.38 (m, 1 H), 5.03 (d, J = 2.2 Hz, 2H), 4.62 - 4.49 (m, 1 H), 4.39 - 4.18 (m, 2H), 4.02 - 3.92 (m, 1 H).

Example 483: 2-[3-Fluoro-6-(2-fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yll-N,N- dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 92. MS

(ES!): mass calcd. for C17H15F2N3O, 315.1 ; m/z found, 318.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.55 - 8.50 (m, 1 H), 8.09 (s, 1 H), 7.65 (d, J = 2.1 Hz, 1 H), 7.63 - 7.56 (m, 1 H), 7.51 - 7.44 (m, 1 H), 7.40 - 7.33 (m, 2H), 5.20 (s, 2H), 3.08 (s, 3H), 2.84 (s, 3H). -[3-Fluoro-6-(2-fluoro-3-methyl-phenyl)pyrrolor3.2-blpyridin -1 ^■

The title compound was prepared in a manner analogous to Example 92. MS (ES!): mass calcd. for C18H17F2N3O, 329.1 ; m/z found, 330.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-de) δ 8.50 (t, J = 1 .9 Hz, 1 H), 8.09 - 8.02 (m, 1 H), 7.84 (d, J = 2.1 Hz, 1 H), 7.42 - 7.36 (m, 1 H), 7.34 (t, J = 7.4 Hz, 1 H), 7.23 (t, J = 7.6 Hz, 1 H), 5.20 (s, 2H), 3.08 (s, 3H), 2.84 (s, 3H), 2.32 (d, J = 2.1 Hz, 3H).

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for Ci ₇ H ₁₆ FN ₃ G, 297.1 ; m/z found, 298.1 [M+H] ⁺ . Ή NMR (500 MHz, DMSO-de) δ 8.69 (d, J = 1 .8 Hz, 1 H), 8.19 (t, J = 2.2 Hz, 1 H), 7.78 - 7.72 (m, 2H), 7.61 (d, J = 2.2 Hz, 1 H), 7.54 - 7.48 (m, 2H), 7.43 - 7.37 (m, 1 H), 5.21 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H).

Example 496: 2-f3-Fluoro-6-(m-tolyl)pyrrolo[3,2-blpyridin-1 -yl1-N,N-dimethyl acetamide.

The title compound was prepared in a manner analogous to Example 92. MS (ES!): mass calcd. for Ci ₈ Hi ₈ FN ₃ 0, 31 1 .1 ; m/z found, 312.1 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.59 (d, J = 1 .8 Hz, 1 H), 8.05 (t, J = 2.1 Hz, 1 H), 7.53 - 7.50 (m, 1 H), 7.49 - 7,45 (m, 1 H), 7.43 (d, J = 2.3 Hz, 1 H), 7.36 (t, J = 7.7 Hz, 1 H), 7.24 - 7.19 (m, 1 H), 5.22 (s, 2H), 3.19 (s, 3H), 2.98 (s, 3H), 2.43 (s, 3H).

Example 497: 1 -(Azetidin-1 -yl)-2-(3-fluoro-6-phenyl-pyrrolof3,2-blpyridin-1 -

The title compound was prepared in a manner analogous to Example 182. MS (ES!): mass calcd. for 0 ₈ Η ₁₆ ΡΝ ₃ 0, 309.1 ; m/z found, 310.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.70 (d, J = 1 .9 Hz, 1 H), 8.18 (t, J = 2.2 Hz, 1 H), 7.81 - 7.72 (m, 2H), 7.65 (d, J = 2.3 Hz, 1 H), 7.56 - 7.48 (m, 2H), 7.45 - 7.38 (m, 1 H), 4.96 (s, 2H), 4.22 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.34 - 2.22 (m, 2H).

The title compound was prepared in a manner analogous to Example 182. MS (ES!): mass calcd. for C20H2QFN3O, 337.2; m/z found, 338.1 [M+H] ^{+ 1} H NMR (400 MHz, CD3OD) δ 7.80 (d, J = 1 .7 Hz, 1 H), 7.26 (t, J = 2.1 Hz, 1 H), 6.74 - 6.67 (m, 2H), 6.66 (d, J = 2.3 Hz, 1 H), 6.59 (t, J = 7.6 Hz, 1 H), 6.47 - 6.41 (m, 1 H), 4.15 (s, 2H), 3.49 (t, J = 7.7 Hz, 2H), 3.26 (t, J = 7.8 Hz, 2H), 1 .94 (q, J = 7.6 Hz, 2H), 1 .62 - 1 .52 (m, 2H), 0.49 (t, J = 7,6 Hz, 3H), νΠ-Ν,Ν-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 92. S (ESI): mass calcd. for Ci ₈ H ₁₅ F4N ₃ 0, 365.1 ; m/z found, 366.0 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.75 (d, J = 1 .9 Hz, 1 H), 8.30 (t, J = 2.2 Hz, 1 H), 8.12 - 8.05 (m, 2H), 7.80 - 7.73 (m, 2H), 7.66 (d, J = 2.2 Hz, 1 H), 5.24 (s, 2H), 3.1 1 (s, 3H), 2.85 (s, 3H).

Example 500: 2-[3-Fluoro-6-f2-fluoro-3-(trifluoromethyl)phenvnpyrrolof3,2 - blpyridin-1 -yl1-N,N-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 92. MS

(ES!): mass calcd. for C ₈ H ₁₄ F5N ₃ 0, 383.1 ; m/z found, 384.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-ofe) δ 8.54 (d, J = 1 .8 Hz, 1 H), 8.17 (s, 1 H), 7.98 - 7.91 (m, 1 H), 7.88 - 7.82 (m, 1 H), 7.70 (s, 1 H), 7.60 - 7.53 (m, 1 H), 5.22 (s, 2H), 3,08 (s, 3H), 2.84 (s, 3H). -[3-Fluoro-6-(2,3,4-trifluorophenyl)pyrrolor3,2-blpyridin-1 -vil-

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for C17H13F4N3O, 351.1; m/z found, 352.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-ofe) δ 8.52 (t, J = 1.9 Hz, 1H), 8.14-8.11 (m, 1H), 7.89 (d, J = 2.2 Hz, 1 H), 7.52 - 7.43 (m, 2H), 5.20 (s, 2H), 3.08 (s, 3H), 2.84 (s, 3H).

Exam le 502: 2-f6-(2,4-Difluoro-3-methyl-phenyl)-3-fluoro-pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for CisHieFsNsO, 347.1; m/z found, 348.1 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 8.48 (t, J = 1.9 Hz, 1 H), 8.05 (s, 1 H), 7.65 (d, J = 2.2 Hz, 1H), 7.50-7.41 (m, 1H), 7.21 (t, J = 8.7 Hz, 1H), 5.19 (s, 2H), 3.08 (s, 3H), 2.84 (s, 3H), 2.24 (s, 3H).

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for C17H15CIFN3O, 331.1; m/z found, 332.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.26 (t, J = 2.2 Hz, 1 H), 7.83 (t, J = 1 .9 Hz, 1 H), 7.77 - 7.73 (m, 1 H), 7.64 (d, J = 2.2 Hz, 1 H), 7.53 (t, J = 7.9 Hz, 1 H), 7.48 - 7.43 (m, 1 H), 5.22 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H). Example 504: 2-[6-(3-Chloro-4-fluoro-phenyl)-3-fluoro-pyrrolo[3,2-blpyrid in-1 -

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for C ₇ Hi ₄ CjF ₂ N ₃ 0, 349.1 ; m/z found, 350.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 8.71 (d, J = 1 .9 Hz, 1 H), 8.25 (t, J = 2.2 Hz, 1 H), 7.99 (dd, J = 7.1 , 2.3 Hz, 1 H), 7.82 - 7.76 (m, 1 H), 7.64 (d, J = 2.2 Hz, 1 H), 7.56 (t, J = 9.0 Hz, 1 H), 5.21 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H).

Example 505: 2-[6-(3-Ethylphenyl)-3-fluoro-pyrrolo[3 ₁ 2-blpyridin-1 -yll-N,N-

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for Ci ₉ H ₂ oFN ₃ 0, 325.2; m/z found, 326.1 [M+H] ⁺ . Ή NMR (500 MHz, DMSO-cfe) δ 8.67 (d, J = 1 .9 Hz, 1 H), 8.15 (t, J = 2.2 Hz, 1 H), 7.60 (d, J = 2.2 Hz, 1 H), 7.58 - 7.56 (m, 1 H), 7.54 (d, J = 8.0 Hz, 1 H), 7.41 (t, J = 7.6 Hz, 1 H), 7.25 (d, J = 7.6 Hz, 1 H), 5,21 (s, 2H), 3, 10 (s, 3H), 2.85 (s, 3H), 2.70 (q, J = 7.5 Hz, 2H), 1 .25 (t, J = 7.6 Hz, 3H). -(Azetidin-1 -yl)-2-f3-fluoro-6-(3-fluorophenyl)pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 182. MS (ESI): mass calcd. for C18H15F2N3O, 327.1 ; m/z found, 328.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 8.77 - 8.71 (m, 1 H), 8.26 (s, 1 H), 7.70 - 7.62 (m, 3H), 7.59 - 7.53 (m, 1 H), 7.27 - 7.20 (m, 1 H), 4.96 (s, 2H), 4.23 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.34 - 2.22 (m, 2H). Example 507: 1 -(3-Fluoroazetidin-1 -yl)-2-r3-fluoro-6-(2- fluorophenvDpyrrolofS^-blpyridin-l -yllethanone.

The title compound was prepared in a manner analogous to Example 182. MS (ES!): mass calcd. for Ci ₈ Hi ₄ F ₃ IM ₃ 0, 345.1 ; m/z found, 346.1 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.54 (t, J = 1 .8 Hz, 1 H), 8.08 - 8.02 (m, 1 H), 7.62 - 7.55 (m, 1 H), 7,52 (d, J = 2.3 Hz, 1 H), 7.47 - 7.41 (m, 1 H), 7.35 - 7.29 (m, 1 H), 7.29 - 7.22 (m, 1 H), 5.48 - 5.30 (m, 1 H), 5.00 (d, J = 2.2 Hz, 2H), 4.61 - 4.51 (m, 1 H), 4.42 - 4.28 (m, 2H), 4.14 - 4.03 (m, 1 H), -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-i4-fluoro-3

The title compound was prepared in a manner analogous to Example 182. MS (ESI): masscalcd. for Ci ₉ H ₁₃ F ₆ N30, 413.1; m/z found, 414.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.75 (d, J = 1.9 Hz, 1 H), 8.29 (t, J = 2.2 Hz, 1 H), 8.17 -8.11 (m, 1H), 8.09 (dd, J = 6.9, 2.4 Hz, 1H), 7.70 (d, J = 2.1 Hz, 1H), 7.69- 7.65 (m, 1H), 5.55-5.37 (m, 1H), 5.03 (d, J = 2.1 Hz, 2H), 4.60-4.49 (m, 1H), 4.37-4.19 (m, 2H), 4,03-3.90 (m, 1H).

Example 509: 2-[6-{3.5-Difluorophenyl)-3-fluoro-pyrroloi3.2-blpyridin-1 -yll-

Ν,Ν-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 92. MS

(ES!): mass calcd. for C17H14F3N3O, 333.1; m/z found, 334.0 [M+H] ⁺ . ^! H NMR (500 MHz, DMSO-C ) δ 8.78 (d, J = 1.9 Hz, 1 H), 8.32 (t, J = 2.2 Hz, 1 H), 7.67 (d, J = 2.1 Hz, 1 H), 7.61 - 7.54 (m, 2H), 7.29 - 7.21 (m, 1 H), 5.21 (s, 2H), 3.11 (s, 3H), 2.86 (s, 3H). -[3-Fluoro-6-(3-fluorophenyl)pyrrolor3,2-blpyridin-1 -vn-N,N-

The title compound was prepared in a manner analogous to Example 92. MS (ESi): mass calcd. for C17H15F2N3O, 315.1 ; m/z found, 318.0 [M+H] ⁺ . ^! H NMR (500 MHz, CD ₃ OD) 5 8.62 (d, J = 1 .8 Hz, 1 H), 8.12 (t, J = 2.1 Hz, 1 H), 7.56 - 7.44 (m, 4H), 7.16 - 7.10 (m, 1 H), 5.23 (s, 2H), 3.19 (s, 3H), 2.98 (s, 3H).

Exam le 51 1 : 2-f3-Chloro-6-(4-fluorophenyl)pyrrolo[3,2-blpyridin-1 -yll-N _l N-

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci ₇ Hi ₅ C!FN ₃ 0, 331 .1 ; m/z found, 332.0 [M+H] ⁺ . Ή NMR (500 MHz, DMSO-o ^* ₆ ) δ 8.70 (d, J = 1 .9 Hz, 1 H), 8.21 (d, J = 1 .9 Hz, 1 H), 7.83 - 7.76 (m, 2H), 7.75 (s, 1 H), 7.38 - 7.32 (m, 2H), 5.26 (s, 2H), 3.1 1 (s, 3H), 2.86 (s, 3H).

The title compound was prepared in a manner analogous to Example 146. MS

(ESI): mass calcd. for C17H15CIFN3O, 331 .1 ; m/z found, 332.0 [M+H] ⁺ . ¹ H N MR (500 MHz, DMSO-cfe) δ 8.56 (t, J = 1.9 Hz, 1H), 8.12 (dd, J = 1.9, 1.1

Hz, 1 H), 7.79 (s, 1 H), 7.63 - 7.56 (m, 1 H), 7.51 - 7.44 (m, 1 H), 7.40 - 7.33 (m, 2H), 5.26 (s, 2H), 3.09 (s, 3H), 2.85 (s, 3H). Example 513: 2-[3-Chloro-6-(2-fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridi n-1 - yll-N,N-dimethyl-ac&tamide.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C ₈ Hi7CIFN ₃ G, 345.1; m/z found, 346.0 [M+H] ⁺ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.54 (t, J = 1.9 Hz, 1 H), 8.03 (t, J = 1.4 Hz, 1 H), 7.62 (s, 1H), 7.39-7.33 (m, 1H), 7.32-7.25 (m, 1H), 7.18 (t, J = 7.6 Hz, 1H), 5.26 (s, 2H), 3.18 (s, 3H), 2.97 (s, 3H), 2.35 (d, J = 2.3 Hz, 3H).

Example 514: 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1-yl)-N,N-dimethy l- acetamide.

The title compound was prepared in a manner analogous to Example 146. MS (ES!): mass calcd. for C17H16CIN3O, 313.1; m/z found, 314.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-C ) δ 8.72 (d, J = 1.9 Hz, 1 H), 8.22 (d, J = 1.9 Hz, 1 H), 7.79 -7.71 (m, 3H), 7.55-7.48 (m, 2H), 7.44-7.37 (m, 1H), 5.27 (s, 2H), 3.11 (s, 3H), 2.86 (s, 3H). Example 515: 2-[3-Chloro-6-(m-tolyl)pyrrolo[3,2-blpyridin-1-yl1-N,N-dimet hyl- acetamide.

The title compound was prepared in a manner analogous to Example 148. MS (ESi): mass calcd. for Ci ₈ H ₁₈ CIN ₃ 0, 327.1; m/z found, 328.1 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-de) δ 8.70 (d, J = 1.9 Hz, 1 H), 8.19 (d, J = 1.9 Hz, 1 H), 7.74 (s, 1 H), 7.57 (s, 1 H), 7.53 (d, J = 7.8 Hz, 1 H), 7.39 (t, J = 7.6 Hz, 1 H), 7.22 (d, J= 7.5 Hz, 1H), 5.27 (s, 2H), 3.11 (s, 3H), 2.86 (s, 3H), 2.41 (s, 3H).

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C18H14CIF4N3O, 399.1; m/z found, 400.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-d ₆ ) δ 8.77 (d, J = 1.9 Hz, 1 H), 8.31 (d, J = 1.9 Hz, 1H), 8.17-8.10(m, 1H), 8.08 (dd, J = 6.8, 2.4 Hz, 1H), 7.80 (s, 1H), 7.71 - 7.63 (m, 1H), 5.28 (s, 2H), 3.11 (s, 3H), 2.86 (s, 3H).

The title compound was prepared in a manner analogous to Example 146, MS (ES!): mass calcd. for Ci ₈ H _i4 ClF ₄ N ₃ 0, 399.1 ; m/z found, 400.0 [M+H . H NMR (500 MHz, DMSO-d ₆ ) δ 8.58 (t, J = 1 .8 Hz, 1 H), 8.21 - 8.18 (m, 1 H), 7.94 (t, J = 7.3 Hz, 1 H), 7.89 - 7.82 (m, 2H), 7.57 (t, J = 7.8 Hz, 1 H), 5.28 (s, 2H), 3.09 (s, 3H), 2.85 (s, 3H).

Example 518: 2-i3-Chloro-6-(2,3,4-trifluorophenyl)pyrroioi3,2-b1pyridin-1 ~yl1~ N.N-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C17H13C 3N3O, 367.1 ; m/z found, 368.0 [M+Hf. H NMR (500 MHz, DMSO-efe) δ 8.56 (t, J = 1 .9 Hz, 1 H), 8.19 - 8.12 (m, 1 H), 7.83 (s, 1 H), 7.53 - 7.43 (m, 2H), 5.26 (s, 2H), 3.09 (s, 3H), 2.85 (s, 3H). Example 519: 2-[3-Chloro-6-(2,4-difluoro-3-methyl-phenyl)pyrrolo[3,2- blpyridin-l -yll-N.N-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C ₈ Hi ₆ CIF2N ₃ 0, 363.1 ; m/z found, 364.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-d ₆ ) δ 8.52 (d, J = 1 .8 Hz, 1 H), 8.09 (d, J = 1 .8 Hz, 1 H), 7.79 (s, 1 H), 7.50 - 7.41 (m, 1 H), 7.22 (t, J = 9.2 Hz, 1 H), 5.25 (s, 2H), 3.09 (s, 3H), 2.85 (s, 3H), 2.25 (s, 3H). -[3-Chloro-6-(3-chloro-4-fluoro-phenyl)pyrrolo[3,2-blpyridin -

The title compound was prepared in a manner analogous to Example 148. MS (ES!): mass calcd. for C17H14CI2FN3O, 365.0; m/z found, 366.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-tfe) δ 8.74 (d, J = 1 .9 Hz, 1 H), 8.28 (d, J = 1 .9 Hz, 1 H), 7.99 (dd, J = 7.1 , 2.4 Hz, 1 H), 7.82 - 7.78 (m, 1 H), 7.78 (s, 1 H), 7.56 (t, J = 9.0 Hz, 1 H), 5.27 (s, 2H), 3.1 1 (s, 3H), 2.86 (s, 3H).

The title compound was prepared in a manner analogous to Example 146. MS (ES!): mass calcd. for Ci ₈ Hi ₅ CiFN ₃ 0, 343.1 ; m/z found, 344.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-tfe) δ 8.58 (t, J = 1 .9 Hz, 1 H), 8.12 (s, 1 H), 7.82 (s, 1 H), 7.64 - 7.58 (m, 1 H), 7.52 - 7.45 (m, 1 H), 7.41 - 7.34 (m, 2H), 5,00 (s, 2H), 4.24 (t, J = 7.6 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.32 - 2.23 (m, 2H).

Example 522: 1 -(Azetidin- -yl)-2-f3-chloro-6-(2-fluoro-3-methy

The title compound was prepared in a manner analogous to Example 146, MS (ES!): mass calcd. for C19H17C N3O, 357.1 ; m/z found, 358.0 [M+H] ⁺ . ¹ H N MR (500 MHz, DMSO-cfe) δ 8.55 (t, J= 1.9 Hz, 1H), 8.10 (dd, J = 1.9, 1.1 Hz, 1 H), 7.81 (s, 1 H), 7.43 - 7.37 (m, 1 H), 7.37 - 7.32 (m, 1 H), 7.24 (t, J = 7.6 Hz, 1 H), 5.00 (s, 2H), 4.23 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.33 (d, J = 2.1 Hz, 3H), 2.31 - 2.23 (m, 2H).

Example 523: 1-(Azetidin-1-yl)-2-f3-chloro-6-r4-fluoro-3- (trifluoromethyl)phenyllpyrrolo[3,2-blpyridin-1-yl1ethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C19H14CIF4N3O, 411.1; m/z found, 412.0 [M+H] ⁺ H NMR (500 MHz, DMSO-d ₆ ) δ 8.78 (d, J = 1.9 Hz, 1 H), 8.32 (d, J = 1.9 Hz, 1H), 8.17- 8.12 (m, 1H), 8,10 (dd, J = 6.8, 2.4 Hz, 1H), 7.83 (s, 1H), 7.72- 7.65 (m, 1H), 5.03 (s, 2H), 4.24 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.33-2.24 (m, 2H),

Example 524: 1-(Azetidin-1-yl)-2-r3-chloro-6-r2-fluoro-3-

The title compound was prepared in a manner analogous to Example 146, MS (ES!): mass calcd. for 0 ₉ Η ₁₄ 0!Ρ4Ν3θ, 411.1; m/z found, 412.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-d ₆ ) δ 8.59 (t, J = 1.8 Hz, 1 H), 8.20 (t, J = 1.5 Hz, 1 H), 7.99 - 7.93 (m, 1 H), 7,89 - 7,83 (m, 2H), 7.58 (t, J = 7.9 Hz, 1 H), 5.02 (s 4.24 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.32 - 2.23 (m, 2H).

Example 525: 1 -(Azetidin-1 -yl)-2-f3-chloro-6-(2,4-difluoro-3-methyl-

The title compound was prepared in a manner analogous to Example 146. MS (ES!): mass calcd. for C19H16C 2N3O, 375.1 ; m/z found, 376.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-d ₆ ) δ 8.53 (t, J = 1 .9 Hz, 1 H), 8.09 (t, J = 1 .4 Hz, 1 H), 7.82 (s, 1 H), 7.50 - 7,43 (m, 1 H), 7.23 (t, J = 8.5 Hz, 1 H), 4.99 (s, 2H), 4.23 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.32 - 2.22 (m, 5H).

Example 526: 1 -(Azetidin-1 -yl)-2-f3-chloro-6-(3-chlorophenyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci ₈ H ₁₅ Ci ₂ N ₃ 0, 359.1 ; m/z found, 360.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.76 (d, J = 1 .9 Hz, 1 H), 8.29 (d, J = 1 .9 Hz, 1 H), 7.85 (t, J = 1 .9 Hz, 1 H), 7.81 (s, 1 H), 7.78 - 7.72 (m, 1 H), 7.55 (t, J = 7.8 Hz, 1 H), 7.51 - 7.45 (m, 1 H), 5.03 (s, 2H), 4.25 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.34 - 2.23 (m, 2H). -(Azetidin-1 -yl)-2-f3-chloro-6-(3-chloro-4-fluorO'

The title compound was prepared in a manner analogous to Example 148. MS (ESI): mass calcd. for CisHuC FNsO, 377.0; m/z found, 378,0 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 8.75 (d, J = 1 .9 Hz, 1 H), 8.28 (d, J = 2.0 Hz, 1 H), 8.01 (dd, J = 7.1 , 2.3 Hz, 1 H), 7.83 - 7.78 (m, 2H), 7.61 - 7.54 (m, 1 H), 5.02 (s, 2H), 4.24 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.33 - 2.24 (m, 2H).

Example 528: 1 -(Azetidin-1 -yl)-2-f3-chloro-6-(3-chloro-2-fluoro- phenv0pyrrolof3,2-blpyridin-1 -yl1ethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C18H14CI2FN3O, 377.0; m/z found, 378.0 [M+H] ⁺ H NMR (500 MHz, DMSO-d ₆ ) δ 8.58 (s, 1 H), 8, 17 (s, 1 H), 7.85 (s, 1 H), 7.66 (t, J = 7.4 Hz, 1 H), 7.58 (t, J = 7.5 Hz, 1 H), 7.38 (t, J = 7.9 Hz, 1 H), 5.01 (s, 2H), 4.24 (t, J = 7.7 Hz, 2H), 3.90 (t, J = 7.7 Hz, 2H), 2.32 - 2.23 (m, 2H).

-(Azetidin-1 -vh-2-f3-chloro-6-f3-

The title compound was prepared in a manner analogous to Example 148. MS (ESI): mass calcd. for 375.1 ; m/z found, 376,0 [M+Hf. H NMR (500 MHz, CD ₃ OD) δ 8.69 (d, J = 1 .7 Hz, 1 H), 8.18 (d, J = 1 .8 Hz, 1 H), 7.92 - 7.84 (m, 2H), 7.68 - 7.56 (m, 3H), 6.87 (t, J = 56.2 Hz, 1 H), 5.03 (s, 2H), 4.33 (t, J = 7.7 Hz, 2H), 4.07 (t, J = 7.9 Hz, 2H), 2.44 - 2.34 (m, 2H), Example 530: 1 -(Azetidin-1 -yl)-2-f3-chloro-6-(3-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ES!): mass calcd. for C18H15CIFN3O, 343.1 ; m/z found, 344.0 [M+H] ^{+ 1} H NMR (500 MHz, DMSO-cfe) δ 8.79 - 8.75 (m, 1 H), 8.31 - 8.27 (m, 1 H), 7.81 (d, J = 2.1 Hz, 1 H), 7.68 - 7.61 (m, 2H), 7.60 - 7.52 (m, 1 H), 7.24 (t, J = 8.2 Hz, 1 H), 5.02 (d, J = 2.3 Hz, 2H), 4.25 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.5 Hz, 2H), 2.33 - 2.25 (m, 2H).

-[3-Chloro-6-(3-fluorophenyl)pyrrolof3,2-blpyridin-1 -vn-N,N-

The title compound was prepared in a manner analogous to Example 148. MS (ESi): mass calcd. for C17H15C N3O, 331 .1 ; m/z found, 332.0 [Μ+Η] ^÷ . ¹ H NMR (500 MHz, CD ₃ OD) δ 8.66 (d, J = 1 .9 Hz, 1 H), 8.15 (d, J = 1 .9 Hz, 1 H), 7.62 (s, 1 H), 7.57 - 7.46 (m, 3H), 7.17 - 7.09 (m, 1 H), 5.29 (s, 2H), 3.20 (s, 3H), 2.98 (s, 3H).

The title compound was prepared in a manner analogous to Example 146. MS (ES!): mass calcd. for Ci ₈ Hi ₄ ClF2N ₃ 0, 361 .1 ; m/z found, 362.0 [M+H] ⁺ . H

NMR (500 MHz, CD ₃ OD) δ 8.68 (d, J = 1 .9 Hz, 1 H), 8.20 (d, J = 1 .9 Hz, 1 H), 7.68 (s, 1 H), 7.39 (dd, J = 8.7, 2.2 Hz, 2H), 7.03 - 6.96 (m, 1 H), 5.03 (s, 2H), 4.39 - 4.30 (m, 2H), 4.08 (t, J = 7.8 Hz, 2H), 2.44 - 2.35 (m, 2H).

Example 533: 1 -(Azetidin- -yl)-2-f3-chloro-6-(3-ethylphenyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 146, MS (ES!): mass calcd. for C ₂ OH2QC!N ₃ 0, 353.1 ; m/z found, 354.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-ds) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.19 (d, J = 1 .9 Hz, 1 H), 7.78 (s, 1 H), 7.60 - 7,57 (m, 1 H), 7,58 - 7.53 (m, 1 H), 7.43 (t, J = 7.6 Hz, 1 H), 7.26 (d, J = 7.5 Hz, 1 H), 5.02 (s, 2H), 4.24 (t, J = 7.7 Hz, 2H), 3.91 (t, J = 7.7 Hz, 2H), 2.71 (q, J = 7.6 Hz, 2H), 2,32 - 2,23 (m, 2H), 1 .26 (t, J = 7.6 Hz, 3H).

Example 534: 2-[3-Chloro-6-(3-chlorophenvi)pyrroloi3.2--blpyridin-1 --yll-N,N- dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 146. MS (ES!): mass calcd. for CiyHisC!aNaO, 347.1 ; m/z found, 348.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.75 (d, J = 1 .9 Hz, 1 H), 8.30 (d, J = 1 .9 Hz, 1 H), 7.84 (t, J = 1 .9 Hz, 1 H), 7.78 (s, 1 H), 7.77 - 7.73 (m, 1 H), 7.54 (t, J = 7,8 Hz, 1 H), 7.49 - 7.45 (m, 1 H), 5.28 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H).

Example 535: 2-i3-Chloro-6-(2-fluorophenyl)pyrroloi3,2-b]pyridin-1 -yll-1 ~(3- fluoroazetidin-1 -ypethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd, for Ci ₈ H ₁₄ C]F2N ₃ 0, 361 .1 ; m/z found, 362.0 [M+Hf. H NMR (500 MHz, DMSO-d ₆ ) δ 8.58 (t, J = 1 .9 Hz, 1 H), 8.14 (dd, J = 1 .9, 1 .1 Hz, 1 H), 7.83 (s, 1 H), 7.64 - 7.57 (m, 1 H), 7.51 - 7.45 (m, 1 H), 7.41 - 7.34 (m, 2H), 5,55 - 5,37 (m, 1 H), 5.07 (d, J = 3.7 Hz, 2H), 4.63 - 4.52 (m, 1 H), 4.40-4.29 (m, 1H), 4.29-4.16 (m, 1H), 4.02-3.89 (m, 1H).

Example 536: 2-[3-Chloro-6-(2-fluoro-3-methyl-phenyl)pyrrolof3 ₁ 2-blpyridin-1 - -1 -(3-fluoroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C19H16C 2N3O, 375.1; m/z found, 376.0 [M+Hf. H NMR (500 MHz, DMSO-efe) δ 8.58 - 8.54 (m, 1 H), 8.11 (s, 1 H), 7.82 (d, J = 1.6 Hz, 1 H), 7.40 (t, J = 7.5 Hz, 1 H), 7.35 (t, J = 7.4 Hz, 1 H), 7.24 (t, J = 7.7 Hz, 1 H), 5.55 - 5.38 (m, 1 H), 5.07 (d, J = 3.9 Hz, 2H), 4.64 - 4.51 (m, 1 H), 4.41 -4.29 (m, 1H), 4.29-4.19 (m, 1H), 4.02-3.90 (m, 1H), 2.33 (s, 3H).

Example 537: 2-[3-Chloro-6-(3,5-difluorophenyl)pyrrolof3,2-blpyridin-1 -yil-1 - -fluoroazetidin-1 -yDethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for CisHiaC!FaNsO, 379.1; m/z found, 380.0 [M+Hf. H NMR (500 MHz, DMSO-d ₆ ) δ 8.82 (d, J = 1.9 Hz, 1 H), 8.35 (d, J = 2.0 Hz, 1 H), 7.84 (s, 1 H), 7.61 - 7.55 (m, 2H), 7.31 - 7.23 (m, 1 H), 5.57 - 5.40 (m, 1 H), 5.08 (s, 2H), 4.65 - 4.53 (m, 1 H), 4.41 - 4.31 (m, 1 H), 4.31 - 4.20 (m, 1H), 4.04-3.93 (m, 1H). -[3-Chloro-6-r2-fluoro-3-(trifluoromethyl)phenyllpyrrolor3,2 -

The title compound was prepared in a manner analogous to Example 148. MS (ESI): mass calcd. for C19H13CIF5N3O, 429.1 ; m/z found, 430.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-tfe) δ 8.60 (t, J = 1 .7 Hz, 1 H), 8.22 - 8.20 (m, 1 H), 7.98 - 7.93 (m, 1 H), 7.89 - 7.83 (m, 2H), 7.58 (t, J = 7.8 Hz, 1 H), 5.55 - 5.38 (m, 1 H), 5.08 (d, J = 3.5 Hz, 2H), 4.63 - 4.52 (m, 1 H), 4.40 - 4.30 (m, 1 H), 4.29 - 4.18 (m, 1 H), 4.02 - 3.91 (m, 1 H).

Example 539: 2-[3-Chloro-6-(2 ₁ 4-difluoro-3-methyl-phenyl)pyrrolo[3 ₁ 2- b]pyridin-1 -yil-1 -(3-fluoroazetidin-l -vDethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ES!): mass calcd. for C ₉ H ₁₅ CIF ₃ N ₃ 0, 393.1 ; m/z found, 394.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-tfe) δ 8.53 (d, J = 2.1 Hz, 1 H), 8.10 (s, 1 H), 7.82 (s, 1 H), 7.50 - 7.42 (m, 1 H), 7.22 (t, J = 8.9 Hz, 1 H), 5.57 - 5.36 (m, 1 H), 5.06 (d, J = 4.1 Hz, 2H), 4.63 - 4.50 (m, 1 H), 4.42 - 4.17 (m, 2H), 4.06 - 3.89 (m, 1 H), 2.25 (s, 3H). -[3-Chloro-6-(3-chloro-4-fluoro-phenyl)pyrrolo[3,2-blpyridin -

The title compound was prepared in a manner analogous to Example 148. MS (ESI): mass calcd. for C18H13CI2F2 3O, 395.0; m/z found, 396.0 [i /!+H] ^÷ . ¹ H NMR (500 MHz, DMSO-tfe) δ 8.75 (d, J = 1 .9 Hz, 1 H), 8.28 (d, J = 1 .9 Hz, 1 H), 8.00 (dd, J = 7.1 , 2.3 Hz, 1 H), 7.82 (s, 1 H), 7.81 - 7.77 (m, 1 H), 7.61 - 7.52 (m, 1 H), 5.57 - 5.39 (m, 1 H), 5.08 (d, J = 2.1 Hz, 2H), 4.64 - 4.52 (m, 1 H), 4.40 - 4.30 (m, 1 H), 4,30 - 4.20 (m, 1 H), 4.03 - 3.90 (m, 1 H).

Example 541 : 2-[3-Chloro-6-(3-chloro-2-fluoro-phenyl)pyrrolo[3,2-blpyridi n-1 - νΠ-1 -(3-fluoroazetidin-l -vDethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESi): mass calcd. for C ₈ H ₁₃ Cl2F ₂ N ₃ 0, 395.0; m/z found, 396.0 [i /!+H] ^÷ . ¹ H NMR (500 MHz, DMSO-tfe) δ 8.59 (t, J = 1 .8 Hz, 1 H), 8.19 (t, J = 1 .5 Hz, 1 H), 7.86 (s, 1 H), 7.69 - 7.63 (m, 1 H), 7.61 - 7.56 (m, 1 H), 7.42 - 7.35 (m, 1 H), 5.55 - 5.38 (m, 1 H), 5.07 (d, J = 3.6 Hz, 2H), 4.63 - 4.52 (m, 1 H), 4.40 - 4.30 (m, 1 H), 4.29 - 4.19 (m, 1 H), 4.02 - 3.90 (m, 1 H), -r3-Chloro-6-f3-ethylphenvnpyrrolof3.2-blpyridin-1 -νΠ-1 -(3-

The title compound was prepared in a manner analogous to Example 148. MS (ES!): mass calcd. for C20H19CIFN3O, 371 .1 ; m/z found, 372.0 [Μ+Η] ^÷ . ¹ H NMR (500 MHz, DMSO-tfe) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.20 (d, J = 1 .9 Hz, 1 H), 7.78 (s, 1 H), 7.60 - 7.52 (m, 2H), 7.43 (t, J = 7.6 Hz, 1 H), 7.26 (d, J = 7.5 Hz, 1 H), 5.56 - 5.39 (m, 1 H), 5.08 (d, J = 3.0 Hz, 2H), 4.63 - 4.53 (m, 1 H), 4.41 - 4.30 (m, 1 H), 4.30 - 4.20 (m, 1 H), 4.03 - 3.90 (m, 1 H), 2.71 (q, J = 7.6 Hz, 2H), 1 .26 (t, J = 7.6 Hz, 3H).

Example 543: 2-[3-Chloro-6-(3-fluorophenyl)pyrrolof3,2-blpyridin-1 -yll-1 -(3- fluoroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci8Hi ₄ CiF ₂ N ₃ 0, 361 .1 ; m/z found, 362,0 [M+Hf. H NMR (500 MHz, DMSO-d ₆ ) δ 8.78 (d, J = 1 .9 Hz, 1 H), 8.29 (d, J = 1 .9 Hz, 1 H), 7.82 (s, 1 H), 7.66 - 7.61 (m, 2H), 7.59 - 7.53 (m, 1 H), 7.28 - 7.20 (m, 1 H), 5.57 - 5.39 (m, 1 H), 5,08 (d, J = 2.3 Hz, 2H), 4.64 - 4.53 (m, 1 H), 4.40 - 4.30 (m, 1 H), 4.30 - 4.20 (m, 1 H), 4.04 - 3.91 (m, 1 H). -[3-Chloro-6-(3-chloro-2-fluoro-phenyl)pyrrolo[3,2-blpyridin -

The title compound was prepared in a manner analogous to Example 148. MS (ES!): mass calcd. for Ci ₇ H ₁₄ Cl ₂ FN ₃ 0, 365.0; m/z found, 366.0 [M+H] ⁺ . H NMR (400 MHz, CD ₃ OD) δ 8.55 (t, J = 1 .9 Hz, 1 H), 8.08 (t, J = 1 .5 Hz, 1 H), 7.66 (s, 1 H), 7.57 - 7.48 (m, 2H), 7.34 - 7.26 (m, 1 H), 5.28 (s, 2H), 3.18 (s, 3H), 2.97 (s, 3H).

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for 377.0; m/z found, 378.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-d ₆ ) δ 8.76 (d, J = 1 .9 Hz, 1 H), 8.30 (d, J = 1 .9 Hz, 1 H), 7.84 (t, J = 1 .9 Hz, 1 H), 7.82 (s, 1 H), 7.78 - 7.73 (m, 1 H), 7.55 (t, J = 7.9 Hz, 1 H), 7.49 - 7.45 (m, 1 H), 5.56 - 5.39 (m, 1 H), 5.09 (d, J = 2.0 Hz, 2H), 4.64 - 4.53 (m, 1 H), 4.42 - 4.30 (m, 1 H), 4.30 - 4.20 (m, 1 H), 4.04 - 3.92 (m, 1 H). -[3-Chloro-6-f3-(difluoromethvnphenyllpyrrolof3,2-blpyridin-

The title compound was prepared in a manner analogous to Example 146. MS (ESi): mass calcd. for C19H15CIF3N3O, 393.1 ; m/z found, 394.0 [M+H] ⁺ . H NMR (400 MHz, DMSO-tfe) δ 8.76 (s, 1 H), 8.28 (s, 1 H), 7.96 - 7.92 (m, 2H), 7.82 (s, 1 H), 7.73 - 7.56 (m, 2H), 7.30 - 6.95 (m, 1 H), 5.60 - 5.36 (m, 1 H), 5.10 (s, 2H), 4.66 - 4.50 (m, 1 H), 4.43 - 4.17 (m, 2H), 4.05 - 3.89 (m, 1 H). Example 5^

To a solution of compound of 1 -(azetidin-1 -yl)-2-[2-methyl-6-(m- tolyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone (Example 41 , 104 mg, 0.32 mmol) and Selectfluor® (135 mg, 0.38 mmol) in AGN (0.63 mL) was added pyridine (0.18 mL, 2.34 mmol). The reaction mixture was stirred at room temperature for 12 hours, concentrated under reduced pressure. Purification (FCC, Si0 ₂ , 50- 100% EtOAc in hexanes) afforded the title compound (6.4 mg, 6%). MS (ESI): mass calcd. for C20H20FN3O, 337.2; m/z found, 338.1 [M+H] ⁺ . H NMR (500 MHz, CD3OD) δ 8.52 (d, J = 1 .7 Hz, 1 H), 8.01 (dd, J = 2.4, 1.8 Hz, 1 H), 7.50 (s, 1 H), 7.48 - 7.44 (m, 1 H), 7.36 (t, J = 7.6 Hz, 1 H), 7.23 - 7.18 (m, 1 H), 4.94 (s, 2H), 4.32 (t, J = 7.7 Hz, 2H), 4.07 (t, J = 7.8 Hz, 2H), 2.43 (s, 3H), 2.41 (d, J = 2.0 Hz, 3H), 2.41 - 2.34 (m, 2H). -(Azetidin-1 -yl)-2-f6-(3,4-difluorophenyl)-3-methyl-pyrrolor3,2-

The title compound was prepared in a manner analogous to Example 27. S (ESI): mass calcd. for C19H17F2N3G, 341 .1 ; m/z found, 342.0 [M+H] ⁺ . ¹ H NMR (300 MHz, CDCI3) δ 8.61 (s, 1 H), 7.83 (s, 1 H), 7.47 - 7.37 (m, 1 H), 7.37 - 7.29 (m, 1 H), 7.29 - 7.18 (m, 2H), 4.77 (s, 2H), 4.09 (t, J = 7.7 Hz, 2H), 4.00 (t, J = 7.6 Hz, 2H), 2.45 (s, 3H), 2.38 - 2.21 (m, 2H). Example 549: 2-i6-(3,4-Difluorophenyl)-3-methyl-pyrroloi3,2-blpyridin-1 -yil- -dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C18H17F2N3O, 329.1 ; m/z found, 330.0 [M+H] ⁺ . H NMR (300 MHz, CDCI3) δ 8.50 (s, 1 H), 8.05 (s, 1 H), 7.41 - 7,21 (m, 4H), 5.09 (s, 2H), 3.14 (s, 3H), 2.96 (s, 3H), 2.47 (s, 3H).

Example 550: 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C2OH ₂ QF ₃ 0, 337.2; m/z found, 338.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.61 (d, J = 1 .8 Hz, 1 H), 8.02 (d, J = 1 .8 Hz, 1 H), 7.57 - 7.47 (m, 2H), 7.43 - 7.34 (m, 2H), 7.19 (d, J = 7.6 Hz, 1 H), 5.58 - 5.44 (m, 1 H), 5.00 (s, 2H), 4.61 - 4.42 (m, 1 H), 4.37 - 4.14 (m, 2H), 4.04 - 3.86 (m, 1 H), 2.41 (s, 3H), 2.30 (s, 3H).

Example 551 : 2-[6-(3.4-Difluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yll-1 - -fluoroazetidin-1 -yl)ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for 359.1 ; m/z found, 360.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1 .7 Hz, 1 H), 8.10 (d, J = 1 .7 Hz, 1 H), 7.89 - 7.79 (m, 1 H), 7,64 - 7.50 (m, 2H), 7.40 (s, 1 H), 5.59 - 5.30 (m, 1 H), 4.99 (s, 2H), 4.61 - 4.43 (m, 1 H), 4.35 - 4.15 (m, 2H), 4.04 - 3.87 (m, 1 H), 2.30 (s, 3H).

The title compound was prepared in a manner analogous to Example 27. MS

(ESI): mass calcd. for C20H18F3N3O, 373.1 ; m/z found, 374.0 [M+H] ⁺ . ¹ H NMR (300 MHz, CDCI3) δ 8.71 (s, 1 H), 8.25 (br. s, 1 H), 7.89 - 7.78 (m, 2H), 7,76 - 7.57 (m, 2H), 7.45 (s, 1 H), 4.89 (s, 2H), 4,34 - 4.22 (m, 2H), 4.13 (t, J Hz, 2H), 2.59 (s, 3H), 2.50 - 2.32 (m, 2H).

Example 553: N _; N-Dimethyl-2-i3-methyl-8-i3-

The title compound was prepared in a manner analogous to Example 27. MS (ESi): mass calcd. for C19H18F3N3O, 361 .1 ; m/z found, 362.0 [M+H] ⁺ . ^! H NMR (300 MHz, CDCI3) δ 8.67 (s, 1 H), 7.86 - 7.74 (m, 3H), 7.67 - 7.54 (m, 2H), 7.22 (s, 1 H), 4.98 (s, 2H), 3.15 (s, 3H), 3.01 (s, 3H), 2.47 (s, 3H).

Exam le 554: 1 -(3-Fluoroazetidin-1 -yl)-2-f3-methyl-6-[3-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H17F4N3O, 391 .1 ; m/z found, 392.0 [M+H] ⁺ . H !MMR (300 MHz, DMSO-cfe) δ 8,69 (d, J = 1 .9 Hz, 1 H), 8.17 (d, J = 1 .9 Hz, 1 H), 8.10 - 7.99 (m, 2H), 7.74 (d, J = 4.7 Hz, 2H), 7.42 (s, 1 H), 5.59 - 5,28 (m, 1 H), 5.02 (s, 2H), 4.61 - 4.42 (m, 1 H), 4.37 - 4.15 (m, 2H), 4.04 - 3.87 (m, 1 H), 2.31 (s, 3H). -[6-(3.5-Difluorophenyl)-3-methyl-pyrrolof3,2-blpyridin-1 -yll-

The title compound was prepared in a manner analogous to Example 27, MS 5 (ESI): mass calcd. for C18H17F2N3O, 329.1 ; m/z found, 330.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-de) δ 8,70 (d, J = 1 .9 Hz, 1 H), 8.18 (d, J = 2.0 Hz, 1 H), 7.59 - 7.48 (m, 2H), 7.38 (s, 1 H), 7.28 - 7.15 (m, 1 H), 5.19 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H), 2.30 (s, 3H). 0 -(Azetidin- -yl)-2-[6-(3,5-difluorophenyl)-3-methyl-pyrrolof3,2-

TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 2277.. MMSS ((EESSII)):: mmaassss ccaallccdd.. ffoorr 334411 ..11 ;; mm//zz ffoouunndd,, 334422..00 [[MM++HH]] ⁺⁺ .. ¹¹ HH NNMMRR

1155 ((330000 MMHHzz,, DDMMSSOO--dd ₆₆ )) δδ 88..7711 ((dd,, JJ == 22..00 HHzz,, 11 HH)),, 88..1188 ((dd,, JJ == 22..00 HHzz,, 11 HH)),, 77..6600 -- 77..4499 ((mm,, 22HH)),, 77..4422 ((ss,, 11 HH)),, 77..3300 -- 77..1155 ((mm,, 11 HH)),, 44..9944 ((ss,, 22HH)),, 44..2200 ((tt,, JJ == 77..77 HHzz,, 22HH)),, 33..9900 ((tt,, JJ == 77..77 HHzz,, 22HH)),, 22..3344 -- 22..1199 ((mm,, 55HH))..

EExxaammppllee 555577:: 22--i[66--((33,,55--DDiifflluuoorroopphheennyyll))--33--mmee tthhvyll--ppyyrrrrooiiooii33,,22--bb]]ppyyrriiddiinn--11 --yyllll--NN--

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for Ci9Hi ₉ F ₂ IM ₃ 0, 343.1 ; m/z found, 344.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.70 (s, 1 H), 8.23 - 8.07 (m, 1 H), 7.60 - 7.46 (m, 2H), 7.45 - 7.35 (m, 1 H), 7,27 - 7.15 (m, 1 H), 5.20 (s, 0.8H), 5.17 (s, 1 .2H), 3.48 (q, J = 7.0 Hz, 1 .2H), 3.32 - 3.20 (m, 0.8H), 3.09 (s, 1 .8H), 2.82 (s, 1 .2H), 2.30 (s, 3H), 1.24 (t, J = 7.0 Hz, 1 .2H), 1 ,03 (t, J = 7.1 Hz, 1 .8H).

Example 558: 2-[6-(4-Fluorophenyl)-3-methyl-pyrrolof3,2-blpyridin-1 -vn-N.N- dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for Ci ₈ Hi ₈ FN ₃ 0, 31 1 .1 ; m/z found, 312.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 8.59 (d, J = 1 .9 Hz, 1 H), 8.02 (d, J = 1 .9 Hz, 1 H), 7.80 - 7.70 (m, 2H), 7.39 - 7.27 (m, 3H), 5.18 (s, 2H), 3.1 1 (s, 3H), 2.85 (s, 3H), 2.30 (s, 3H).

Example 559: N-Ethyl-2-r6-(4-fluorophenyl)-3-methyl-pyrrolof3,2-blpyridin -1 - -Ν-methyl-acetam ide.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C19H20FN3O, 325.2; m/z found, 326.0 [M+H] ⁺ H NMR (300 MHz, CDCI3) δ 8.65 (s, 1 H), 7.65 - 7.51 (m, 3H), 7.21 - 7.09 (m, 3H), 4.89 (d, J = 9.2 Hz, 2H), 3.53 - 3.38 (m, 2H), 3.07 - 2.90 (m, 3H), 2.44 (s, 3H), 1 .29 - 1 .05 (m, 3H). -Ethyl-2-r6-(2-fluoro-3-methyl-phenvn-3-methyl-pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 27. S (ESI): mass calcd. for C ₂₀ H ₂ 2FN ₃ G, 339.2; m/z found, 340.0 [M+H] ⁺ . 1 H NMR (300 MHz, DMSO-ds) δ 8.44 (s, 1 H), 7.93 - 7.84 (m, 1 H), 7.42 - 7.26 (m, 3H), 7.25 - 7.16 (m, 1 H), 5.18 (s, 0.8H), 5.14 (s, 1 .2H), 3.45 (d, J = 7.1 Hz, 1 .2H), 3.32 - 3.21 (m, 0.8H), 3.06 (s, 1 ,8H), 2.81 (s, 1 .2H), 2.32 (s, 3H), 2.30 (s, 3H), 1 .20 (t, J = 7.1 Hz, 1 ,2H), 1 .01 (t, J = 7.0 Hz, 1 ,8H).

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H20FN3O, 337.2; m/z found, 337.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-cfe) δ 8.45 (s, 1 H), 7.91 (s, 1 H), 7.42 - 7.27 (m, 3H), 7.22 (t, J = 7.5 Hz, 1 H), 4.91 (s, 2H), 4.18 (t, J = 7.6 Hz, 2H), 3.89 (t, J = 7.7 Hz, 2H), 2.36 - 2.17 (m, 8H). Example 562: 2-[6-(2-Fluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3,2-b]pyrid in- -νΠ-Ν, Ν-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C19H2QF 3O, 325.2; m/z found, 326.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.47 - 8.42 (m, 1 H), 7.92 - 7.88 (m, 1 H), 7.42 - 7.26 (m, 3H), 7,26 - 7, 16 (m, 1 H), 5.17 (s, 2H), 3.09 (s, 3H), 2.84 (s, 3H), 2.35 - 2.27 (m, 6H).

Example 563: 1 -(3-Fluoroazetidin-1 -yl)-2-f6-(2-fluoro-3-methyl-phenyl)-3-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H19F2 3O, 355.1 ; m/z found, 356.0 [M+H] ⁺ . H NMR (300 MHz, CDCI3) δ 8.66 (s, 1 H), 7.74 (s, 1 H), 7.38 - 7.10 (m, 4H), 5.33 - 5.02 (m, 1 H), 4.77 (s, 2H), 4.41 - 4.06 (m, 2H), 3.91 - 3.74 (m, 2H), 2.45 (s, 3H), 2.36 (s, 3H).

Example 564: 1 ~(3,3~Difluoroazetidin~1 -yl)-2-[6-(2-fluoro-3-methyl-phenyl)-3-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H18F3N3O, 373.1 ; m/z found, 373.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-de) δ 8.48 - 8.44 (m, 1 H), 7.97 - 7.93 (m, 1 H), 7.42 - 7.27 (m, 3H), 7.26 - 7.18 (m, 1 H), 5.05 (s, 2H), 4.70 (t, J = 12.5 Hz, 2H), 4.35 (t, J = 12.6 Hz, 2H), 2.36 - 2.26 (m, 6H). -[6-(2-Fluoro-3-methyl-phenyl)-3-methyl-pyrrolor3,2-blpyridi n-

TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 2277.. MMSS ((EESSII)):: mmaassss ccaallccdd.. ffoorr CC22 HH2222FFNN33GO,, 335511 ..22;; mm//zz ffoouunndd,, 335522..00 [[MM++HH]] ⁺⁺ .. ΉΉ ! NMIMV!RR ((330000 MMHHzz,, CCDDCCII33)) δδ 88..6600 ((ss,, 11 HH)),, 77..7755 ((ss,, 11 HH)),, 77..4499 -- 77..0066 ((mm,, 44HH)),, 44..8833 ((ss,, 22HH)),, 33..5511 ((tt,, JJ == 66..99 HHzz,, 22HH)),, 33..4422 ((tt,, JJ == 66..77 HHzz,, 22HH)),, 22..4422 ((ss,, 33HH)),, 22..3355 ((ss,, 33HH)),, 22..0066 -- 11 ..9955 ((mm,, 22HH)),, 11 ..9922 -- 11 ..8822 ((mm,, 22HH))..

--νyΠn--ΝN,, ΝN--ddiimmeetthhyyll--aacceettaammiiddee..

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C19H20FN3O, 325.2; m/z found, 326.0 [M+H] ⁺ . ' H NMR (300 MHz, DMSO-de) δ 8.58 (d, J = 1 .8 Hz, 1 H), 8.01 (d, J = 1 .9 Hz, 1 H), 7.67 - 7.60 (m, 1 H), 7.59 - 7.51 (m, 1 H), 7.33 (s, 1 H), 7.25 (t, J = 9.1 Hz, 1 H), 5.18 (s, 2H), 3.1 1 (s, 3H), 2.85 (s, 3H), 2.33 (s, 3H), 2.29 (s, 3H).

Example 567: 2-[3-Methyl-6-f3-(trifluoromethyl)phenvnpyrrolof3,2-blpyridi n-1 -

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C21H20F3N3O, 387.2; m/z found, 388.0 [M+H] ⁺ . ¹ H NMR (300 MHz, CDCI3) δ 8.88 (s, 1 H), 7.91 - 7.76 (m, 2H), 7.70 (s, 1 H), 7.65 - 7.50 (m, 2H), 7.20 (s, 1 H), 4,85 (s, 2H), 3.64 - 3.41 (m, 4H), 2.43 (s, 3H), 2.15 - 1.97 (m,2H), 1.97-1.81 (m,2H).

Example 568: N-Ethyl-N-methyl-2-f3-methyl-6-[3-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H20F3N3O, 375.2; m/z found, 376.0 [M+H] ⁺ . H NMR (300 MHz, CDCI3) δ 8.68 (s, 1 H), 7.88 - 7.76 (m, 2H), 7.69 - 7.51 (m, 3H), 7.18 (s, 1H), 4.92 (d, J= 8.7 Hz, 2H), 3.59-3.34 (m, 2H), 3.08 (s, 1.5H), 2.98 (s, 1.5H), 2.44 (s, 3H), 1.25 (t, J = 7.2 Hz, 1.5H), 1.14 (t, J =7.1 Hz, 1.5H).

Example 569: 1-(3,3-Difluoroazetidin-1-yl)-2-f3-methyl-6-f3-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H16F5N3O, 409.1; m/z found, 410.0 [M+H] ⁺ . H NMR (300 MHz, CDCI3) δ 8.75 (s, 1 H), 7.89 - 7.78 (m, 2H), 7.72 - 7.57 (m, 3H), 7.16 (s, 1 H), 4.85 (s, 2H), 4.39 (t, J = 12.0 Hz, 2H), 4.00 (t, J = 11.5 Hz, 2H), 2.46 (s, 3H). -(Azetidin-1 -vn-2-r3-methyl-6-(3A5-

The title compound was prepared in a manner analogous to Example 27, MS (ESI): mass calcd. for C ₉ Hi ₆ F3N ₃ 0, 359.1 ; m/z found, 360.0 [M+H] ⁺ . H !MMR (300 MHz, DMSO-cfe) δ 8,69 (d, J = 1 .7 Hz, 1 H), 8.16 (d, J = 1 .7 Hz, 1 H), 7.79 (dd, J = 9.6, 6,8 Hz, 2H), 7,42 (s, 1 H), 4.93 (s, 2H), 4.19 (t, J = 7.6 Hz, 2H), 3.90 (t, J = 7.6 Hz, 2H), 2.38 - 2.15 (m, 5H). Example 571 : N.N-Dimethyl-2-i3-methyl-6-(3,4,5-trifluorophenyl)pyrrolo[3, 2-

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C18H16F3N3O, 347.1 : m/z found, 348.0 [M+H] ⁺ . ^! H NMR (300 MHz, DMSO-ds) δ 8.69 (d, J = 1 .6 Hz, 1 H), 8.15 (d, J = 1 .5 Hz, 1 H), 7.77 (dd, J = 9.5, 6.8 Hz, 2H), 7.41 (d, J = 17.8 Hz, 1 H), 5.18 (s, 2H), 3.12 (s, 3H), 2.86 (s, 3H), 2.30 (s, 3H).

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C19H21 N3O, 307.2; m/z found, 308.0 [M+H] ⁺ . H NMR (300 MHz, CDCI3) δ 8.57 (s, 1 H), 7.96 (s, 1 H), 7.42 - 7.18 (m, 5H), 5.06 (s, 2H), 3.16 (s, 3H), 3.01 (s, 3H), 2.44 (s, 3H), 2.42 (s, 3H).

Example 573: N,N-Dimethyl-2-i3-niethyl-6-(4-methyl-2-thienyl)pyrroloi3,2

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C17H19N3OS, 313.1 ; m/z found, 314.0 [M+H] ⁺ . ¹ H NMR (300 MHz, CDCI3) δ 8.68 (d, J = 1 .6 Hz, 1 H), 7.68 (s, 1 H), 7.14 (d, J = 3.8 Hz, 2H), 6.88 (s, 1 H), 4.90 (s, 2H), 3.1 1 (s, 3H), 3,00 (s, 3H), 2.41 (s, 3H), 2.30 (s, 3H). Example 574: 1 -(Azetidin-1 -yl)-2-f3-methyl-6-(4-methyl-2-thienyl)pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for Ci ₈ Hi ₉ N ₃ OS, 325.1 ; m/z found, 326.0 [M+H] ⁺ . ¹ H NMR (300 MHz, CDCI3) δ 8,70 (s, 1 H), 7.73 (s, 1 H), 7.18 (s, 1 H), 7.14 (s, 1 H), 6.89 (s, 1 H), 4.72 (s, 2H), 4.09 (t, J = 7.7 Hz, 2H), 3.85 (t, J = 7.7 Hz, 2H), 2.39 (s, 3H), 2.31 (s, 3H), 2.27 - 2.21 (m, 2H). -(3-Fluoroazetidin-1 -yl)-2-[3-methvi-6-(4-methyl-2

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for Ci ₈ Hi ₈ FN ₃ OS, 343.1 ; m/z found, 344.0 [M+H] ⁺ . H NMR (300 MHz, CDCI ₃ ) 6 8.76 (d, J = 1 .7 Hz, 1 H), 7.65 (s, 1 H), 7.18 (s, 1 H), 7.10 (s, 1 H), 6.90 (s, 1 H), 5.29 - 5.04 (m, 1 H), 4.76 (s, 2H), 4.40 - 4.09 (m, 2H), 3.82 (dd, J = 21 .7, 4.4 Hz, 2H), 2.42 (s, 3H), 2.32 (s, 3H). Example 576: N,N-Dimethyl-2-(3-methyl-6-phenyl-pyrrQio[3,2-b]pyridin-1 -

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for Ci ₈ H ₁₉ N ₃ 0, 293.2; m/z found, 294.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-cfe) δ 8.62 (d, J = 1 .9 Hz, 1 H), 8.04 (d, J = 1 .9 Hz, 1 H), 7.77 - 7.70 (m, 2H), 7.49 (t, J = 7.6 Hz, 2H), 7.38 (d, J = 7.3 Hz, 1 H), 7.33 (s, 1 H), 5.18 (s, 2H), 3.1 1 (s, 3H), 2.85 (s, 3H), 2.30 (s, 3H),

Example 577: N-Ethyi-N-methyl-2-(3-methyl--6-phenyl--pyrrolo[3,2-b]pyridi n-1 - vDacetamide.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C19H21 N3O, 307.2; m/z found, 308.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-d ₆ ) δ 8.62 (d, J = 2.0 Hz, 1 H), 8.01 (dd, J = 9.3, 2.0 Hz, 1 H), 7.72 (d, J = 7.6 Hz, 2H), 7.49 (t, J = 7.6 Hz, 2H), 7.42 - 7.30 (m, 2H), 5.20 (s, 5 0.8H), 5.16 (s, 1 .2H), 3.53 - 3.41 (m, 0.8H), 3.33 - 3.26 (m, 1.2H), 3.08 (s, 1 .8H), 2,82 (s, 1 .2H), 2.30 (s, 3H), 1 .22 (t, J = 7.0 Hz, 1 .2H), 1 ,02 (t, J = 7.1 Hz, 1.8H).

Example 578: 1 -(3-Fluoroazetidin-1 -yl)-2-(3-methyl-6-phenyl-pyrrolor3,2-

10 blpyridin-1 -vDethanone.

TThhee ttiittllee ccoommppoouunndd wwaass pprreeppaarreedd iinn aa mmaannnneerr aannaallooggoouuss ttoo EExxaammppllee 2277.. MMSS ((EESS!!)):: mmaassss ccaallccdd.. ffoorr CC1199HH1188FFNN33OO,, 332233..11 ;; mm//zz ffoouunndd,, 332244..00 [[MM++HH]] ⁺⁺ . ¹¹ HH NNMMRR ((330000 MMHHzz,, DDMMSSOO--ddss)) δδ 88..6644 ((dd,, JJ == 11 ..99 HHzz,, 11 HH)),, 88..0066 ((dd,, JJ == 11 ..99 HHzz,, 11 HH)),, 77..7777 1155 -- 77..6688 ((mm,, 22HH)),, 77..5577 -- 77..4466 ((mm,, 22HH)),, 77..4433 -- 77..3333 ((mm,, 22HH)),, 55..5599 -- 55..2299 ((mm,, 11 HH)),, 55..0000 ((ss,, 22HH)),, 44..6611 -- 44..4422 ((mm,, 1 HH)),, 44..3388 -- 44..1155 ((mm,, 22HH)),, 44..0055 -- 33..8855 ((mm,, 11 HH)),, 22..3300 ((ss,, 33HH))..

EExxaammppllee 557799:: 11 --((33,,33--DDiifflluuoorrooaazzeettiiddiinn--11 --vyll))--22--((33--mmeetthhvyll--66--pphheennvyll--ppyyrrrr oolloo[[33,.22--

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for Ci ₉ Hi ₇ F ₂ jM ₃ O, 341 .1 ; m/z found, 342.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.63 (d, J = 1 .9 Hz, 1 H), 8.06 (d, J = 1 .9 Hz, 1 H), 7.73 (d, J = 7,6 Hz, 2H), 7,50 (t, J = 7.6 Hz, 2H), 7.43 - 7.32 (m, 2H), 5.07 (s, 2H), 4.71 (t, J = 12.5 Hz, 2H), 4.36 (t, J = 12.7 Hz, 2H), 2.30 (s, 3H).

Example 580: 1 -(3-Fluoroazetidin-1 -yl)-2-f6-(4-fluoro-3-methyl-phenyl)-3-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H19F2 3O, 355.1 ; m/z found, 356.0 [M+H] ⁺ . H NMR (300 MHz, CDC ) δ 8.60 (s, 1 H), 7.89 (s, 1 H), 7.40 (d, J = 6.2 Hz, 2H), 7.23 (s, 1 H), 7.10 (t, J = 8.8 Hz, 1 H), 5.27 - 5.01 (m, 1 H), 5.01 - 4.76 (m, 2H), 4.47 - 3.95 (m, 4H), 2.44 (s, 3H), 2.35 (s, 3H).

Example 581 : 1 -(Azetidin-1 -yi)-2-i3-methyl-6-(m-toiyl)pyrroloi3,2-b1pyridin-1 - yilethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C20H21 N3O, 319.2; m/z found, 320.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-ds) δ 8.61 (d, J = 1 .7 Hz, 1 H), 8.01 (d, J = 1 .7 Hz, 1 H), 7.53 (d, J = 12.9 Hz, 2H), 7.37 (d, J = 7.7 Hz, 2H), 7.19 (d, J = 7.4 Hz, 1 H), 4.93 (s, 2H), 4.18 (t, J = 7.6 Hz, 2H), 3.89 (t, J = 7.6 Hz, 2H), 2.41 (s, 3H), 2.33 - 2.17 (m, 5H). -(Azetidin-1 -vn-2-r3-methyl-6-(2.3.4-

The title compound was prepared in a manner analogous to Example 27. S (ESI): mass calcd. for C19H16F3N3G, 359.1 ; m/z found, 360.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 8.47 (s, 1 H), 7.97 (s, 1 H), 7.56 - 7.39 (m, 3H), 4.92 (s, 2H), 4.19 (t, J = 7.6 Hz, 2H), 3.89 (t, J = 7.7 Hz, 2H), 2.30 (s, 3H), 2.28 - 2.18 (m, 2H). Example 583: N,N-Dimethyl-2-i3-niethyl-6-(2,3.4-trifluorophenvnpyrrolo[3, 2- b]pyridin-1 -yl]acetamide.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C ₈ H ₁₆ F ₃ N ₃ 0, 347.1 : m/z found, 348.0 [M+H] ⁺ . H NMR (300 MHz, DMSO- fe) δ 8.46 (s, 1 H), 7.96 (s, 1 H), 7.54 - 7.37 (m, 3H), 5.18 (s, 2H), 3.09 (s, 3H), 2.84 (s, 3H), 2.31 (s, 3H). -Ethyl-N-methyl-2-f3-methyl-6-(2.3,4-

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for Ci9H ₁₈ F ₃ N ₃ 0, 361 .1 ; m/z found, 362.0 [M+H] ⁺ . ^! H NMR (300 MHz, DMSO-cfe) δ 8.46 (s, 1 H), 7.99 - 7.90 (m, 1 H), 7.53 - 7.38 (m, 3H), 5.19 (s, 0.8H), 5.15 (s, 1 .2H), 3.45 (q, J = 7.0 Hz, 0.8H), 3.30 - 3.25 (m, 1 .2 H), 3.06 (s, 1 .8H), 2.81 (s, 1 .2H), 2.31 (s, 3H), 1 .21 (t, J = 7.1 Hz, 1 .2H), 1 .01 (t, J = 7.1 Hz, 1 .8H).

Example 585: 1 -(Azetidin-1 -yl)-2-[6-[2-fluoro-3-(trifluoromethyl)phenvn-3-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass ca!cd. for C20H17F4N3O, 391 .1 ; m/z found, 392.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-cfe) δ 8.49 (s, 1 H), 8.02 (s, 1 H), 7.93 (t, J = 7.6 Hz, 1 H), 7.82 (t, J = 6.9 Hz, 1 H), 7.56 (t, J = 7.8 Hz, 1 H), 7.45 (s, 1 H), 4.93 (s, 2H), 4.19 (t, J = 7.6 Hz, 2H), 3.89 (t, J = 7.6 Hz, 2H), 2.31 (s, 3H), 2.29 - 2.21 (m, 2H).

Example 586: 2-[6-f2-Fluoro-3-(trifluoromethyl)phenyl1-3-methyl-pyrrolof3 ,2- blpyridin-1 -yl1-N,N-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C19H.17F4N3O, 379.1 ; m/z found, 380.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-cfe) δ 8.50 - 8.45 (m, 1 H), 8.03 - 7.99 (m, 1 H), 7.92 (t, J = 7.6 Hz, 1 H), 7.81 (t, J = 7.2 Hz, 1 H), 7.54 (t, J = 7.8 Hz, 1 H), 7.41 (s, 1 H), 5.19 (s, 2H), 3.09 (s, 3H), 2.84 (s, 3H), 2.31 (s, 3H). -Ethyl-2-r6-f2-fluoro-3-(trifluoromethyl)phenyl1-3-methyl-

The title compound was prepared in a manner analogous to Example 27. S (ESI): mass calcd. for C20H19F4N3O, 393.1 ; m/z found, 394.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.47 (s, 1 H), 8.03 - 7.96 (m, 1 H), 7.92 (t, J = 7.5 Hz, 1 H), 7.81 (t, J = 7.1 Hz, 1 H), 7.54 (t, J = 7.8 Hz, 1 H), 7.47 - 7.39 (m, 1 H), 5.20 (s, 0.8H), 5.17 (s, 1 .2H), 3.45 (q, J = 7.1 Hz, 0.8H), 3.33 - 3.25 (m, 1 .2H), 3.06 (s, 1 .8H), 2.81 (s, 1 .2H), 2.31 (s, 3H), 1 .21 (t, J = 7.1 Hz, 1 .2H), 1 .01 (t, J = 7.1 Hz, 1 .8H).

Example 588: 1 -(3-Fluoroazetidin-1 -yl)-2-f3-methyl-6-f2,3.4-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C19H15F4N3O, 377.1 : m/z found, 378.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-d ₆ ) δ 8.51 - 8.43 (m, 1 H), 7.98 (s, 1 H), 7.52 - 7.40 (m, 3H), 5.59 - 5.30 (m, 1 H), 4,99 (s, 2H), 4,62 - 4.41 (m, 1 H), 4.40 - 4.12 (m, 2H), 4.04 - 3.83 (m, 1 H), 2.31 (s, 3H). -(3-Fluoroazetidin-1 -yl)-2-[6-i2-fiuoro-3-

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C20H16F5N3O, 409.1 ; m/z found, 410.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.52 - 8.46 (m, 1 H), 8.05 - 8.00 (m, 1 H), 7.97 - 7.89 (m, 1 H), 7,87 - 7,77 (m, 1 H), 7.55 (t, J = 7.8 Hz, 1 H), 7.46 - 7.43 (m, 1 H), 5.58 - 5.29 (m, 1 H), 5.00 (s, 2H), 4.61 - 4.41 (m, 1 H), 4.38 - 4.12 (m, 2H), 4.04 - 3.86 (m, 1 H), 2.31 (s, 3H).

Example 590: 2-[6-f2-Fluoro-3-(trifluoromethyl)phenyll-3-methyl-pyrrolo[3 .2- b]pyridin-1 -yll- -pyrroiidin-1 -yl-ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C21 H19F4N3O, 405.1 ; m/z found, 406.0 [M+H] ⁺ . ^! H NMR (300 MHz, DMSO-C ) δ 8.50 - 8.45 (m, 1 H), 8.04 - 8.00 (m, 1 H), 7.92 (t, J = 7.7 Hz, 1 H), 7.82 (t, J = 7.1 Hz, 1 H), 7.55 (t, J = 7.8 Hz, 1 H), 7.45 - 7.42 (m, 1 H), 5.10 (s, 2H), 3.56 (t, J = 6.8 Hz, 2H), 3.34 - 3.25 (m, 2H), 2.32 (s, 3H), 2.01 - 1 .89 (m, 2H), 1 .85 - 1 .72 (m, 2H). -[3-Methyl-6-(2.3,4-trifluorophenvnpyrrolor3.2-blpyridin-1 -yll-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H18F3N3O, 373.1 ; m/z found, 374.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-cfe) δ 8.48 - 8.43 (m, 1 H), 8.00 - 7.96 (m, 1 H), 7.51 - 7.38 (m, 3H), 5.09 (s, 2H), 3.56 (t, J = 6.8 Hz, 2H), 3.34 - 3.25 (m, 2H), 2.31 (s, 3H), 2.00 - 1 .89 (m, 2H), 1 ,86 - 1 .72 (m, 2H). Example 592: 1 -(Azetidin-1 -yl)-2-i6-i ^' 2-fluorophenvn-3-methyl-pyrroio[3.2- b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for Ci ₉ H ₁₈ FN ₃ 0, 323.1 ; m/z found, 324.0 [M+H] ⁺ . Ή NMR (300 MHz, DMSO-cfe) δ 8.50 - 8.44 (m, 1 H), 7.96 - 7.91 (m, 1 H), 7.63 - 7.55 (m, 1 H), 7.49 - 7.27 (m, 4H), 4.91 (s, 2H), 4.19 (t, J = 7.7 Hz, 2H), 3.89 (t, J = 7.7 Hz, 2H), 2.30 (s, 3H), 2.29 - 2,18 (m, 2H).

Example 593: 2-r6-(2-Fluorophenyl)-3-methyl-pyrrolof3.2-blpyridin-1 -yl1-N,N-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for Ci ₈ Hi ₈ FN ₃ 0, 31 1 .1 ; m/z found, 312.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.53 - 8.46 (m, 1 H), 8.02 (s, 1 H), 7.63 - 7.51 (m, 1 H), 7.50 - 7.39 (m, 2H), 7,39 - 7,30 (m, 2H), 5.19 (s, 2H), 3.09 (s, 3H), 2.84 (s, 3H), 2.31 (s, 3H).

Example 594: N-Ethyl-2-f6-(2-fluorophenyl)-3-methyl-pyrrolof3,2-blpyridin -1 - -Ν-methyl-acetam ide.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for Ci ₉ H ₂ oFN ₃ 0, 325.2; m/z found, 326.0 [M+H] ⁺ . Ή NMR (300 MHz, DMSO-d ₆ ) δ 8.49 - 8.44 (m, 1 H), 7.91 (d, J = 7.9 Hz, 1 H), 7.62 - 7.53 (m, 1 H), 7.49 - 7.29 (m, 4H), 5.18 (s, 0.8H), 5.15 (s, 1 .2H), 3.45 (q, J = 7.2 Hz, 0.8H), 3.33 (s, 1 .2H), 3.06 (s, 1 .8H), 2.81 (s, 1 .2H), 2.31 (s, 3H), 1 .20 (t, J = 7.1 Hz, 1 .2H), 1 .01 (t, J = 7.1 Hz, 1 .8H).

(trifluoromethyl)phenyll-3-methyl-pyrrolo[3,2-b]pyridin-1 -yllethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H15F6 3O, 427.1 ; m/z found, 428.0 [M+H] ⁺ . H NMR (300 MHz, DMSO-ds) δ 8.51 - 8.47 (m, 1 H), 8.06 - 8.01 (m, 1 H), 7.93 (t, J =

7.6 Hz, 1 H), 7.82 (t, J = 7.3 Hz, 1 H), 7.55 (t, J = 7.9 Hz, 1 H), 7.44 (s, 1 H),

5.07 (s, 2H), 4.71 (t, J = 12.6 Hz, 2H), 4.35 (t, J = 12.6 Hz, 2H), 2.32 (s, 3H).

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for Ci9Hi ₄ F ₅ N ₃ 0, 395.1 ; m/z found, 396.0 [M+H] ⁺ . H NMR (300 MHz, DMSO- fe) δ 8.50 - 8.45 (m, 1 H), 8.01 - 7.98 (m, 1 H), 7.52 - 7.40 (m, 3H), 5.06 (s, 2H), 4.71 (t, J = 12.6 Hz, 2H), 4.35 (t, J = 12.7 Hz, 2H), 2.31 (s, 3H).

Example 597: 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(2-fluorophenyl)-3-methyl- pyrrolor3,2-blpyridin-1 -yl1ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C19H16F3N3O, 359.1 ; m/z found, 360.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.51 - 8.46 (m, 1 H), 8.00 - 7.93 (m, 1 H), 7,63 - 7.54 (m, 1 H), 7.51 - 7.29 (m, 4H), 5.06 (s, 2H), 4.71 (t, J = 12.4 Hz, 2H), 4.35 (t, J = 12.7 Hz, 2H), 2.31 (s, 3H). -(3-Fluoroazetidin-1-yl)-2-f3-methyl-6-(3,4.5'

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C19H15F4N3O, 377.1; m/z found, 378.0 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-cfe)58.70 (s, 1H), 8.16 (s, 1H), 7.95-7.68 (m, 2H), 7.42 (s, 1H), 5.82-5.17 (m, 1H), 4.99 (s, 2H), 4.65-4.40 (m, 1H), 4.40-4,11 (m, 2H), 4.11 - 3.76 (m, 1 H), 2.30 (s, 3H). Example 599: 2-i3-Chloro-6-(2,5-dimethyl-3-thienyl)pyrrQto[3,2-b]pyridin- 1 -yll- N.N-dimethyl-acelamide.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Ci ₇ H ₁₈ C!N ₃ OS, 347.1; m/z found, 348.0 [M+H] ⁺ . H NMR (400 MHz, CDCI3) δ 8.56 (d, J = 1.7 Hz, 1 H), 7.50 (d, J = 1.7 Hz, 1 H), 7.32 (s, 1H), 6.71 (s, 1H), 4.87 (s, 2H), 3.10 (s, 3H), 3.00 (s, 3H), 2.46 (s, 3H), 2.43 (s, 3H).

-i3-Chloro-6-i3-(trifluoromethyl)phenvnpyrroloi3,2-blpyri din-

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for CisHisC!FsNsO, 381 .1 ; m/z found, 382.0 [ +Hf. H NMR (400 MHz, CDCI ₃ ) δ 8.75 (d, J = 1 .8 Hz, 1 H), 7.84 - 7.81 (m, 1 H), 7.81 - 7.76 (m, 1 H), 7.69 (d, J = 1 .8 Hz, 1 H), 7.67 - 7.55 (m, 2H), 7.36 (s, 1 H), 4.95 (s, 2H), 3.15 (s, 3H), 3.01 (s, 3H).

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for Cr^CIFa^O, 382.1 ; m/z found, 383.0 [M+H] ⁺ . ¹ H NMR (400 MHz, CDCI ₃ ) δ 9.07 (d, J = 1 .8 Hz, 1 H), 8.37 (d, J = 1 .8 Hz, 1 H), 8.01 (d, J = 8.0 Hz, 1 H), 7.95 (t, J = 7.8 Hz, 1 H), 7.66 - 7.60 (m, 1 H), 7.42 (s, 1 H), 4.99 (s, 2H), 3.17 (s, 3H), 3.01 (s, 3H).

Example 602: 2-r3-Chloro-6-(5-chloro-4-methyl-2-thienyl)pyrrolor3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 146, MS (ES!): mass calcd. for C16H15CI2N3OS, 367.0; m/z found, 368.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 8.63 (d, J = 1 .9 Hz, 1 H), 8.12 (d, J = 2.0 Hz, 1 H), 7.74 (s, 1 H), 7.41 (s, 1 H), 5.23 (s, 2H), 3.09 (s, 3H), 2.85 (s, 3H), 2.19 (s, 3H).

Example 603: 2-[3-Chloro-6-f5-(trifluoromethyl)-2-thienyllpyrrolo[3,2-blp yridin- -νΠ-Ν, Ν-dimethyl-acetamide.

The title compound was prepared in a manner analogous to Example 146. MS (ESI): mass calcd. for C16H13CIF3N3OS, 387.0; m/z found, 388.0 [M+H] ⁺ . ¹ H NMR (500 MHz, DMSO-cfe) δ 8.79 (d, J = 1 .9 Hz, 1 H), 8.30 (d, J = 1 .9 Hz, 1 H), 7.80 (s, 1 H), 7.79 - 7,74 (m, 1 H), 7,69 - 7.64 (m, 1 H), 5.26 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H).

Example 604: 2-[6-(Benzothiophen-2-yl)pyrrolof3,2-blpyridin-1 -yl1-N, N-

The title compound was prepared in a manner analogous to Example 106. H NMR (400 MHz, CDCI3) δ 8.85 (d, J = 2.0 Hz, 1 H), 7.82 (d, J = 7.9 Hz, 1 H), 7.80 - 7.74 (m, 2H), 7.56 (s, 1 H), 7.40 - 7.28 (m, 3H), 6.78 (d, J = 3.3 Hz, 1 H), 4.92 (s, 2H), 3.10 (s, 3H), 3.00 (s, 3H), -[3-Fluoro-6-r4-fluoro-3-(trifluoromethyl)phenyllpyrrolof3.2 -

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for C18H14F5N3O, 383.1; m/z found, 384.0 [M+H] ⁺ . H NMR (500 MHz, DMSO-cfe) δ 8.73 (d, J = 1.9 Hz, 1H), 8.30-8.26 (m, 1H), 8.17- 8.04 (m, 2H), 7.72 - 7.63 (m, 2H), 5.22 (s, 2H), 3.10 (s, 3H), 2.85 (s, 3H). -r6-(3-Chloro-2-fluoro-phenyl)-3-fluoro-pyrrolor3,2-blpyridi n-1 -

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for C17H14C 2N3O, 349.1; m/z found, 350.0 [M+Hf. H NMR (500 MHz, DMSO-cfe) δ 8.54 - 8.51 (m, 1H), 8.14 (s, 1H), 7.68 (d, J = 2.2 Hz, 1H), 7.67-7.62 (m, 1 H), 7.59 - 7.54 (m, 1 H), 7.40 - 7.34 (m, 1H), 5.21 (s, 2H), 3.08 (s, 3H), 2.84 (s, 3H).

Example 607: 1 -(3-Fluoroazetidin-1 -yl)-2-f3-fluoro-6-(m-tolyl)pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 92. MS (ES!): mass calcd. for Ci ₉ Hi ₇ F ₂ jM ₃ 0, 341 .1 ; m/z found, 342.1 [M+H] ⁺ . ¹ H NMR (400 MHz, DMSO-ds) δ 8.68 (d, J = 1 .8 Hz, 1 H), 8.16 (t, J = 2.2 Hz, 1 H), 7.64 (d, J = 2,2 Hz, 1 H), 7,57 (s, 1 H), 7.54 (d, J = 8.1 Hz, 1 H), 7.40 (t, J = 7.6 Hz, 1 H), 7.22 (d, J = 7.5 Hz, 1 H), 5.58 - 5.35 (m, 1 H), 5.03 (s, 2H), 4.64 - 4.47 (m, 1 H), 4.40 - 4.16 (m, 2H), 4.04 - 3.89 (m, 1 H), 2,41 (s, 3H).

Example 608: 2-i6-(3-Chloro-4-fluoro-phenyl)-3-fluoro-pyrrolo[3,2-b]pyrid in-1 yll-1 -;3-fluoroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 92. MS (ESI): mass calcd. for 379.1 ; m/z found, 380.0 [M+H] ⁺ H NMR (400 MHz, DMSO-d ₆ ) δ 8.72 (d, J = 1 .9 Hz, 1 H), 8.25 (t, J = 2.2 Hz, 1 H), 8.00 (dd, J = 7.1 , 2.3 Hz, 1 H), 7.84 - 7.74 (m, 1 H), 7.68 (d, J = 2.2 Hz, 1 H), 7.57 (t, J = 9.0 Hz, 1 H), 5.58 - 5.35 (m, 1 H), 5.02 (s, 2H), 4.63 - 4.48 (m, 1 H), 4.40 - 4.15 (m, 2H), 4.07 - 3.87 (m, 1 H).

Example 609: 1 -(Azetidin-1 -vn-2-(3-i ³ H1-6-(4-fiuorQ-3-methylphenvn-1 H- -b]pyridin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 349 substituting tritium gas for H ₂ gas. ³ H NMR (300 MHz, CD ₃ OD) δ 6.97 (s, 1 -[2-Deuterio-6-(4-fluoro-3-methyl-phenyl)pyrrolor3,2-blpyrid in-

carboxylaie. To a solution of 6-(4-fluoro-3-methylphenyl)-1 H-pyrrolo[3,2- bjpyridine (500 mg, 2.21 mmol) in DCM (10 mL) was added (Boc) ₂ 0 (0.57 mL, 2.85 mmol) and DMAP (27 mg, 0.22 mmol) and the reaction mixture was stirred at rt for 1 hour. Water was added and the resulting mixture was extracted with EtOAc, The organic layers were combined, dried, concentrated and purified by FCC (0-100% EtOAc in hexanes) to provide tert-butyl 6-(4~ fluoro-3-methyiphenyl)-1 H-pyrrolo[3,2-b]pyridine-1 -carboxylate (78%, 564 mg).

Step B: 6-(4-Fluoro-3-methylphenyl)-2-duetero-1 H-pyrrolof3,2-blpyridine. To a solution of tert-butyl 6-(4-fluoro-3-methylphenyl)-1 H-pyrroio[3,2-b]pyridine-1 - carboxylate (400 mg, 1 .23 mmol) in THF at -78 °C was added tBuLi (2.89 mL, 4.91 mmol, 1 .7 M in hexanes) and the reaction mixture was stirred for 15 minutes. To the reaction mixture was added CD ₃ C0 ₂ D (0.75 mL, 12.3 mmol) and the reaction mixture was slowly warmed to rt. The reaction mixture was diluted with EtOAc and washed with water. The organic phase was dried, concentrated and purified by FCC (0-100% EtOAc in hexanes) to provide 6- (4-fluoro~3~methylphenyl)-2-duetero-1 H-pyrrolo[3,2~b]pyridine (89 %, 251 mg). Step C: 2-(6-(4-Fluoro-3-niethyiphenyl)-2-duetero-1 H-pyrroio[3,2-blpyridin-1 - vi)-N,N-dimethylacetamide. The title compound was prepared in a manner analogous to Example 66. MS (ESI): mass calcd. for C 8H17DFN3O, 312.1 ; m/z found, [M+H] ⁺ . -[6-(3,5-Difluorophenyl)-3-(trifluoromethyl)pyrrolo[3,2-

Step A: 6-(3,5-Difluorophenyl)-3-iodo-1 H-pyrrolo[3.2-blpyridine. To a solution of 6~(3,5-difluorophenyl)~1 H~pyrroio[3,2-b]pyridine (Intermediate 9, 750mg, 3.5mmol) in D!VIF (10mL) at room temperature was added NIS (1 .1 g, 4,4 mmol). The solution was stirred overnight and water (20 mL) was added in the morning. The reaction mixture was concentrated directly onto silica gel and purified (FCC, SiO , 0-100% EtOAc in hexanes) to afford the title compound (1 .1 g, 97%). ¹ H N R (400 MHz, DMSO) δ 1 1 .96 (s, 1 H), 8,82 - 8.66 (d, J = 2.0 Hz, 1 H), 8.19 - 8.02 (d, J = 2.0 Hz, 1 H), 8.02 - 7.80 (d, J = 2.8 Hz, 1 H), 7.70 - 7.45 (m, 2H), 7.33 - 7.14 (m, 1 H).

Step B: ie/f-Butyi 6-(3.5-difluorophenYl)-3-iodo-1 H-pyrrolof3,2-blpyridine-1 - carboxylate. To a solution 6-(3,5-difluorophenyl)-3-iodo-1 H-pyrrolo[3,2- bjpyridine (1 .13g, 3.2mmol) in DCM (1 GmL) was added DMAP (39mg, 0,32mmol) followed by BOC-anhydride (0,82mL, 3.8mmol). The reaction mixture was stirred for one hour. Water (25m L) and EtOAc (25m L) were added. The organics were extracted, combined, dried ( gS0 ₄ ), filtered and concentrated under reduced pressure. Purification (Si0 ₂ , 0-100% EtOAc in hexanes) afforded the title compound (946mg, 65%). MS(ESI): mass calcd. for C ₈ H ₁₅ F ₂ IN2O2 , 456.04; m/z found, 457.05.

Step C: 6-(3,5-Difiuorophenyl)-3-(trifluoromethyl)-1 H-pyrrolo[3,2-b1pyridine. To a solution of ferf-butyl 6-(3,5-difluorophenyl)-3-iodo-1 H-pyrroio[3,2-b]pyridine- 1 -carboxylate (5G0mg, 1 .1 mmol) in DMF (5mL) was added copper (208mg, 3.3mmol) and diphenyi(frifiuoromethyl)suifonium trifluoromethanesuifonafe (886mg, 2.2mmoi). The mixture was refluxed at 90 °C for 12 hours. The reaction was diluted with water (5 mL) and concentrated onto silica gel.

Purification (FCC, SiO2, 0-100% EtOAc in hexanes) afforded the title compound (177mg, 54%). MS(ESI): mass calcd. for C14H7F5N2, 298,2; m/z found, 299.1 . Step D: 2-(6-(3,5-Difluorophenyl)-3-(trifluoromethyl)-1 H-pyrroloi3.2-blpyridin- a solution of 6-(3,5~difluorophenyl)-3~

(trifluoromethyl)-l H-pyrroio[3,2-b]pyridine (15 mg, 0,05 mmol) in DMF (0.5 mL) at 0 °C was added NaH (6.0 mg, 0.15 mmol, 60% dispersion in oil). The reaction mixture was warmed to room temperature and stirred for 30 minutes and then cooled to 0 °C followed by the addition of a solution of 1 ~(azetidin-1 ~ yi)-2-bromoethanone (10 mg, 0.06 mmol) in DMF (0.5 mL). The reaction mixture was warmed to room temperature and stirred for 12 hours. Water was added and the mixture was extracted with EtOAc. The combined organic layers were dried (MgS0 ₄ ), filtered and concentrated under reduced pressure. HPLC purification via Method A afforded the title compound (1 .7 mg, 8.8%). MS (ESI): mass calcd. for C 8H14F5N3O, 383.1 ; m/z found, [M+H] ⁺ Ή NMR (400 MHz, CD ₃ OD) 5 8,82 - 8.50 (d, 1 H), 8.34 - 8.15 (d, 1 H), 8.03 (s, 1 H), 7.51 - 7.29 (d, J = 8.4 Hz, 3H), 7.1 1 - 6.91 (m, 1 H), 5.37 (s, 2H), 3.22 (s, 2H), 2.99 (s, 2H). -Chloro-1 -(3-pyridylmethyl)-6-f3-

The title compound was prepared in a manner analogous to Example 1 , using 3-cb!oro-6-(3-(trif!uorometby!)pbeny!)-1 H-pyrrolo[3,2-b]pyridine and 3- (bromomethyl)pyridine hydrobromide in step C. MS (ESI): mass caicd. for C20H13CIF3N3, 387.1 ; m/z found, 388.0 [M+H] ⁺ 'H NMR (400 MHz, CDCI ₃ ) δ 5.40 (s, 2 H) 7.27 - 7.32 (m, 1 H) 7.36 - 7.44 (m, 2 H) 7.56 - 7.69 (m, 2 H) 7.72 (d, J =1 .85 Hz, 1 H) 7.76 (d, J =7.63 Hz, 1 H) 7.80 (s, 1 H) 8.49 - 8.67 (m, 2 H) 8.79 (d, J =1 .85 Hz, 1 H)

(trifluoromethvnphenyllpyrrolo[3,2-blpyridine.

The title compound was prepared in a manner analogous to Example 1 , using 6-(3-(trifluoromethyl)phenyl)-1 H-pyrrolo[3,2-b]pyridine and 3- (chloromethyi)pyridazine in step C.MS (ES!): mass calcd. for C19H13F3N4, 354.1 ; m/z found, 355.1 [M+H] ⁺ . H NMR (400 MHz, CDCI ₃ ) δ 5.77 (s, 2 H) 6.88 (dd, J =3.24, 0.69 Hz, 1 H) 6.98 (dd, J =8.55, 1 .39 Hz, 1 H) 7.28 - 7.44 (m, 1 H) 7.50 - 7.65 (m, 3 H) 7.72 - 7.84 (m, 3 H) 8.74 (d, J =1 .85 Hz, 1 H) 9.15 (dd, J =4.97, 1 .50 Hz, 1 H)

The title compound was prepared in a manner analogous to Example 1 , using 3-chioro-6~(4-fluoro-3~methyiphenyl)~1 H~pyrrolo[3,2-b]pyridine and 3~

(chloromethyl)pyridazine hydrochloride in step C. MS (ESI): mass calcd. for C ₁₉ H ₁₄ CIFN ₄ , 352.1 ; m/z found, 353.1 [M+Hf. ¹ H NMR (400 MHz, CDCI ₃ ) δ 2.35 (d, J =1 .16 Hz, 3 H) 5.71 (s, 2 H) 7.09 (s, 2 H) 7.28 - 7.38 (m, 2 H) 7.39 - 7.45 (m, 1 H) 7.49 (s, 1 H) 7.72 (d, J =1 .62 Hz, 1 H) 8.75 (d, J =1 .16 Hz, 1 H) 9.16 (d, J =4.86 Hz, 1 H)

Example 615: 3-Chioro-1 -(pyridazin-3-ylmethyl)-6-i3- (trifluoromethyl)phenyllpyrrolof3,2-blpyridine.

The title compound was prepared in a manner analogous to Example 1 , using 3-chloro-6-(3-(trifluorometbyl)phenyl)-1 H-pyrrolo[3,2-b]pyridine and 3- (ch!oromethyl)pyridazine hydrochloride in step C. MS (ES!): mass calcd. for C ₉ Hi2CIF3N _4! 388.1 ; m/z found, 389.1 [M+H] ⁺ . Ή NMR (400 MHz, CDCI ₃ ) δ 5.74 (s, 2 H) 7.09 (dd, J =8.55, 1 .62 Hz, 1 H) 7.45 (dd, J =8.55, 5.09 Hz, 1 H) 7.54 (s, 1 H) 7.56 - 7.70 (m, 2 H) 7.75 (s, 1 H) 7.78 - 7.86 (m, 2 H) 8.80 (d, J =1 .85 Hz, 1 H) 9.18 (dd, J =4.85, 1 .62 Hz, 1 H) Example 616: 2-[6-(4-Fluoro-3-methyl-phenyl)-3-methyl-pyrrolof3 ₁ 2-b]pyridin- -yll-1 -pyrrolidin-1 -yl-ethanone.

The title compound was prepared in a manner analogous to Example 27, substituting (4-fluoro-3-methylphenyl)boronic acid for (4-fluorophenyl)boronic acid in step A. MS (ES!): mass calcd. for C21 H22FN3O, 351 .2; m/z found, 352 [M+H] ^÷ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8.58 (s, 1 H), 8.01 (s, 1 H), 7.64 (d, J = 7.4 Hz, 1 H), 7.60 - 7.48 (m, 1 H), 7.34 (s, 1 H), 7.25 (t, J = 9.1 Hz, 1 H), 5.09 (s, 2H), 3.58 (t, J = 6.7 Hz, 2H), 3.31 - 3.25 (m, 3H), 2.33 (s, 3H), 2.29 (s, 3H), 2.05 - 1 .88 (m, 2H), 1 .86 - 1 .72 (m, 2H).

Exam le 617: N-Ethyl-2-i6-(4-fluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3,2 -

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C ₂ oH ₂₂ FN ₃ G, 339.2; m/z found, 340 [M+H] ^{+ 1} H NMR (300 MHz, DMSO-ds) δ 8.58 (s, 1 H), 7.98 (d, J = 5.5 Hz, 1 H), 7.63 (d, J = 6.9 Hz, 1 H), 7.59 - 7.48 (m, 1 H), 7.35 (d, J = 8.4 Hz, 1 H), 7.25 (t, J = 9.1 Hz, 1 H), 5.19 (s, 0.8H), 5.15 (s, 1 .2H), 3.52 - 3.42 (m, 1 .2H), 3.30 - 3.24 (m, 0.8H), 3.08 (S.1 .8H), 2.82 (s, 1 .2H), 2.33 (s, 3H), 2.29 (s, 3H), 1 .22 (t, 1 .2H), 1 .02 (t, J = 7.1 Hz, 1 .8H). Exam le 618: 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(4-fluoro-3-methyl-phenyl)-3-

The title compound was prepared in a manner analogous to Example 27. The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C ₂ oHi8F ₃ IM ₃ 0, 373.1 ; m/z found, 374 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.60 (s, 1 H), 8.03 (s, 1 H), 7.64 (d, J = 7.4 Hz, 1 H), 7.60 - 7.51 (m, 1 H), 7,36 (s, 1 H), 7,26 (t, J = 9.1 Hz, 1 H), 5.06 (s, 2H), 4.70 (t, J = 12.5 Hz, 2H), 4.36 (t, J = 12.5 Hz, 2H), 2.33 (s, 3H), 2.30 (s, 3H). Example 619: 2-i6-(3,4-Difluorophenyl)-3-methyl-pyrrQio[3,2-b]pyridin-1 -yll-1 - pyrrolidin-1 -yl-ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd, for C20H19F2N3O, 355.1 ; m/z found, 356 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8.64 (s, 1 H), 8.10 (s, 1 H), 7.90 - 7.76 (m, 1 H), 7.65 - 7.47 (m, 2H), 7.38 (s, 1 H), 5.09 (s, 2H), 3.58 (t, J = 6,7 Hz, 2H), 3,30 - 3.21 (m, 2H), 2.30 (s, 3H), 2.03 - 1 .89 (m, 2H), 1 .87 - 1 .70 (m, 2H).

Example 620: 2-i6-(3,4-Difluorophenyl)-3-methyl-pyrroloi3,2-b1pyridin-1 -yll-N-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C19H19F2N3O, 343.1 ; m/z found, 344 [M+H] ^{+ 1} H NMR (300 MHz, DMSO-d ₆ ) δ 8.63 (s, 1 H), 8.07 (d, J = 8.8 Hz, 1 H), 7.89 - 7.77 (m, 1 H), 7.64 - 7.47 (m, 2H), 7,38 (d, J = 8.3 Hz, 1 H), 5.19 (s, 0.9H), 5.16 (s, 1 .1 H), 3.54 - 3.41 (m, 1 .1 H), 3.30 - 3.24 (m, 0.9H), 3.09 (s, 1 .7H), 2.82 (s, 1 ,3H), 2.29 (s, 3H), 1 .23 (t, J = 7.0 Hz, 1 .3H), 1 .02 (t, J = 7.0 Hz, 1 ,7H),

Example 621 : 1 -(3,3-Difluoroazetidin-1 -yl)-2-f6-(3,4-difluorophenyl)-3-methyl- -blpyridin-1 -yl1ethanone.

The title compound was prepared in a manner analogous to Example 27. S (ES!): mass calcd. for C19H15F4N3O, 377.1 ; m/z found, 378 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8.65 (s, 1 H), 8.10 (s, 1 H), 7.91 - 7.76 (m, 1 H), 7.65 - 7.47 (m, 2H), 7.39 (s, 1 H), 5.06 (s, 2H), 4,70 (t, J = 12,2 Hz, 2H), 4,36 (t, J = 12.6 Hz, 2H), 2.30 (s, 3H).

Example 622: 2-[6-(2,4-Difluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3 ₁ 2-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for 343.1 ; 343 [M+Hf. H NMR (300 MHz, DMSO-cfe) δ 8.41 (s, 1 H), 7.89 (s, 1 H), 7.48 - 7.32 (m, 2H), 7.19 (t, J = 8.7 Hz, 1 H), 5.16 (s, 2H), 3.08 (s, 3H), 2.84 (s, 3H), 2,30 (s, 3H), 2.24 (s, 3H). Example 623: 2-i6-(3.5-Difluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yll-1 -

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C ₂ oHi9F ₂ IM ₃ 0, 355.1 ; m/z found, 356 [M+H] ⁺ . ¹ H NMR (300 MHz, CDCI3) δ 8.66 (d, J = 1 .8 Hz, 1 H), 7.66 (d, J = 1 .8 Hz, 1 H), 7.23 - 7.08 (m, 3H), 6.85 - 6.74 (m, 1 H), 4,83 (s, 2H), 3.58 - 3.42 (m, 4H), 2.44 (s, 3H), 2.12 - 1 .97 (m, 2H), 1 .96 - 1 .82 (m, 2H).

Example 624: 2-[6-(2,4-Difluoro-3-methyl-phenyl)-3-methyl-pyrrolor3,2- b]pyridin-1 -yll-1 -pyrrolidin-1 -yl-ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd, for C2 H21 F2N3O, 389.2; m/z found, 370 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-cfe) δ 8.45 (s, 1 H), 7.98 (s, 1 H), 7.50 - 7.37 (m, 2H), 7.20 (t, J = 8.8 Hz, 1 H), 5.09 (s, 2H), 3.56 (t, J = 6,7 Hz, 2H), 3.29 - 3.17 (m, 2H), 2.31 (s, 3H), 2.24 (s, 3H), 2.03 - 1 .86 (m, 2H), 1 .86 - 1 .70 (m, 2H).

Example 625: 2-i6-(2,4-Difluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H21 F2N3O, 357.2; m/z found, 358 [M+H] ^{+ 1} H NMR (300 MHz, DMSO-cfe) δ 8.42 (s, 1 H), 7.89 (d, J = 6.9 Hz, 1 H), 7.49 - 7.34 (m, 2H), 7.19 (t, J = 8.7 Hz, 1 H), 5.18 (s, 0.8H), 5.14 (s, 1 .2H), 3.52 - 3.38 (m, 2H), 3.06 (s, 1 .8H), 2,81 (s, 1 .2H), 2.30 (s, 3H), 2.24 (s, 3H), 1 .20 (t, J = 6.9 Hz, 1.2H), 1.01 (t, J = 7.0 Hz, 1 .8H).

Example 626: 1 -(3,3-Difluoroazetidin-1 -yl)-2-r6-(2,4-difluoro-3-methyl- phenvn-3-methyl-pyrrolof3,2-blpyridin-1 -yl1ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C20H17F4N3O, 391 .1 ; m/z found, 392 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.44 (s, 1 H), 7.93 (s, 1 H), 7.54 - 7.34 (m, 2H), 7.20 (s, 1 H), 5.05 (s, 2H), 4.82 - 4.61 (m, 2H), 4.45 - 4.24 (m, 2H), 2.30 (s, 3H), 2,24 (s, 3H).

Example 627: 1 -(Azetidin- -yl)-2-f6-(2,4-difluoro-3-methyl-phenyl)-3-methyl-

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C ₂ oHi9F ₂ IM ₃ 0, 355.1 ; 356 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-de) δ 8.43 (s, 1 H), 7,90 (s, 1 H), 7.50 - 7.35 (m, 2H), 7.20 (t, J = 8.7 Hz, 1 H), 4.90 (s, 2H), 4.18 (t, J = 7.4 Hz, 2H), 3.88 (t, J = 7.5 Hz, 2H), 2.30 (s, 3H), 2.28 - 2.18 (m, 5H). -i6-(5-Chloro-2-thienyl)-3-methyl-pyrroloi3.2-b]pyridin-1 -yl]-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for Ci ₆ Hi6C!N ₃ OS, 333.1 ; 334 [M+H] ⁺ . H NMR (300 MHz, DMSO-d ₆ ) δ 8.56 (s, 1 H), 7.99 (s, 1 H), 7.40 (d, J = 3.9 Hz, 1 H), 7.36 (s, 1 H), 7.18 (d, J = 3.9 Hz, 1 H), 5.16 (s, 2H), 3.1 1 (s, 3H), 2.86 (s, 3H), 2.27 (s, 3H).

Example 629: 2-[6-(2.4-Difluoro-3-methyl-phenyl)-3-methyl-pyrrolo[3 ₁ 2- b]pyridin-1 -νΠ-1 -(3-fluoroazetidin-1 -vDethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C20H18F3N3O, 373.1 ; m/z found, 374 [M+H] ^{+ 1} H NMR (300 MHz, CDCI ₃ ) 6 8.61 (s, 1 H), 7.68 (s, 1 H), 7.38 - 7.27 (m, 1 H), 7.15 (s, 1 H), 6.96 (t, J = 8.5 Hz, 1 H), 5.42 - 5.21 (m, 1 H), 4.76 (s, 2H), 4.42 - 4.07 (m, 2H), 3.99 - 3.74 (m, 2H), 2.45 (s, 3H), 2.28 (s, 3H), 1 .60 (s, 3H).

Example 630: N-Ethyl-N-methyl-2-r3-methyl-6-(5-methyl-2-thienvnpyrrolof3, 2- b]pyridin-1 -yi]acetamide.

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C ₈ H ₂ i N ₃ OS, 327.1 ; m/z found, 328 [M+H] ⁺ . H NMR (300 MHz, DMSO-C ) δ 8.55 (s, 1 H), 7.88 (d, J = 7.7 Hz, 1 H), 7.37 - 7.26 (m, 2H), 6.84 (d, J = 2.4 Hz, 1 H), 5.16 (s, 0.8H), 5.13 (s, 1 .2H), 3.52 - 3.40 (m, 2H), 3.08 (s, 1 .8H), 2.82 (s, 1 .2H), 2.48 (s, 3H), 2.27 (s, 3H), 1 .22 (t, J = 7.0 Hz, 1 .2H), 1 ,02 (t, J = 7.1 Hz, 1 .8H).

Example 631 : 2-i3-Methyl-6-(5-niethyl-2-thienvi)pyrroloi3,2-b]pyridin-1 -yll-1 -

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for C19H21 N3OS, 339.1 ; m/z found, 340 [M+H] ⁺ . H NMR (300 MHz, DMSO-ds) δ 8.55 (s, 1 H), 7.94 (s, 1 H), 7.38 - 7.27 (m, 2H), 6.84 (d, J = 2,4 Hz, 1 H), 5,07 (s, 2H), 3.58 (t, J = 6.7 Hz, 2H), 3.30 - 3.24 (m, 2H), 2.48 (s, 3H), 2.27 (s, 3H), 1 .95 (dd, J = 13.3, 6.7 Hz, 2H), 1 .82 (dd, J = 13.4, 6.7 Hz, 2H).

Example 632: 1 -(3,3-Difluoroazetidin-1 -yl)-2-f3-methyl-6-(5-methyl-2- thienyl)pyrrolor3,2-blpyridin-1 -yl1ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C18H17F2N3OS, 361 .1 ; m/z found, 362 [M+H] ⁺ . ¹ H NMR (300 MHz, CDCI ₃ ) 6 8.89 (s, 1 H), 7.70 (s, 1 H), 7.17 (d, J = 3.4 Hz, 1 H), 7.12 (s, 1 H), 6.77 (d, J = 2.5 Hz, 1 H), 4.85 (s, 2H), 4.38 (t, J = 1 1 .9 Hz, 2H), 4.03 (t, J = 1 1 .3 Hz, 2H), 2.53 (s, 3H), 2.41 (s, 3H). -(Azetidin-1 -yl)-2-[3-methyl-6-(5-methyl-2-thienyl)pyrrolof3,2-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C ₈ Hi ₉ N ₃ OS, 325.1 ; m/z found, 326 [M+H] ⁺ . H NMR (300 MHz, CDCI3) δ 8.72 (s, 1 H), 7.64 (s, 1 H), 7.20 - 7.00 (m, 2H), 6.77 (s, 1 H), 4.68 (s, 2H), 4.07 (t, J = 7.6 Hz, 2H), 3.77 (t, J = 7.8 Hz, 2H), 2.53 (s, 3H), 2.41 (s, 3H), 2.22 (dd, J = 15,3, 7.7 Hz, 2H).

The title compound was prepared in a manner analogous to Example 27. MS (ESi): mass calcd. for C ₈ H ₁₈ FN ₃ OS, 343.1 ; m/z found, 344 [M+H] ^{+ 1} H NMR (300 MHz, CDCI ₃ ) 6 8.73 (d, J = 1 .4 Hz, 1 H), 7.61 (d, J = 1 .5 Hz, 1 H), 7.15 (d, J = 3.4 Hz, 1 H), 7,09 (s, 1 H), 6.77 (d, J = 2.3 Hz, 1 H), 5.27 (dd, J = 9,7, 5.1 Hz, 0.5H), 5.13 - 5.01 (m, 0.5H), 4.74 (s, 2H), 4.41 - 4.08 (m, 2H), 3.85 (d, J = 4.2 Hz, 1 H), 3.78 (d, J = 4.2 Hz, 1 H), 2.53 (s, 3H), 2.41 (s, 3H).

Example 635: 2-[6-(3.5-Difluorophenyl)-3-methyl-pyrrolof3 _l 2-b]pyridin-1 -yll-1 - -fluoroazetidin-1 -yl)ethanQne.

The title compound was prepared in a manner analogous to Example 2/. MS (ESI): mass calcd. for C19H16F3N3O, 359.1 ; m/z found, 360 [M+Hf. ¹ H NMR (300 MHz, DMSO-cfe) δ 8.72 (s, 1 H), 8.19 (s, 1 H), 7.54 (d, J = 7.6 Hz, 2H), 7.42 (s, 1 H), 7.23 (t, J = 9.4 Hz, 1 H), 5.60 - 5.51 (m, 0.5H), 5.41 - 5.30 (m, 0.5H), 5.00 (s, 2H), 4.62 - 4.43 (m, 1 H), 4.38 - 4.14 (m, 2H), 4,05 - 3.86 (m, 1 H), 2.30 (s, 3H).

Example 636: 2-i6-(5-Chioro-2-thienyl)-3-methyl-pyrroloi3.2-b]pyridin-1 -yll-1 - (3-fluoroazetidin-1 -yl)ethanone.

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C17H15C N3GS, 383.1; m/z found, 384 [M+H] ^{+ 1} H NMR (300 MHz, D SO-cfe) δ 8.59 (d, J = 1.4 Hz, 1 H), 8.00 (d, J = 1.4 Hz, 1H), 7.45-7.35 (m, 2H), 7.19 (d, J = 3.9 Hz, 1H), 5.61 -5.48(m, 0.5H), 5.41 - 5.30 (m, 0.5H), 4.98 (s, 2H), 4.64 - 4.45 (m, 1 H), 4.40 - 4.15 (m, 2H), 4.06 -3.85 (m, 1H), 2.28 (s, 3H).

Example 637: N,N-Dimethyl-2-3-methyl-6-(5-methyi-2-thienynpyrrolo[3,2-

The title compound was prepared in a manner analogous to Example 27. MS (ESI): mass calcd. for C17H19N3OS, 313.1; m/z found, 314[M+H] ⁺ . H NMR (300 MHz, CDCI ₃ )68.69 (d, J = 1.6 Hz, 1H), 7.58 (d, J= 1.6 Hz, 1H), 7.13- 7.08 (m, 2H), 6.75 (d, J = 2.4 Hz, 1H), 4.86 (s, 2H), 3.09 (s, 3H), 3.01 (s, 3H), 2.52 (s, 3H), 2.40 (s, 3H). -(3-Fluoroazetidin-1 -yl)-2-[6-(2-fluorophenyl)-3-methyl-

The title compound was prepared in a manner analogous to Example 27. MS (ES!): mass calcd. for Ci ₉ Hi ₇ F ₂ N ₃ 0, 341 .1 ; m/z found, 342 [M+H] ⁺ . ¹ H NMR (300 MHz, DMSO-ds) δ 8.48 (s, 1 H), 7.95 (s, 1 H), 7.58 (t, J = 7.8 Hz, 1 H), 7.50 - 7.27 (m, 4H), 5,53 (s, 0.5H), 5.34 (s, 0.5H), 4.98 (s, 2H), 4.59 - 4.43 (m, 1 H), 4.37 - 4.13 (m, 2H), 3.95 (dd, J = 24.6, 1 1 .6 Hz, 1 H), 2.31 (s, 3H).

Example 639: 2-f6-f5-(Difluoromethyl)-2-thienyllpyrrolo[3 ₁ 2-blpyridin-1 -yl1-N, N-

The title compound was prepared in an analogous manner to Intermediate 10, using 6~bromo~1 H~pyrroio[3,2-b]pyridine and 2-bromo-N, N- dimethylacetamide. MS (ESI): mass calcd. for 0·Ι Ι Η Ι ₂ ΒΓΝ ₃ 0, 281 .1 ; m/z found, 282.05 [M+H]+.

Step B: 2-(6-(5-(Difluoromethyl)thiophen-2-yl)-1 H-pyrrolo[3,2-b]pyridin-1 -yl)- N. N-dimethylacetamide. To a solution of 2-bromo-5-(difluoromethyl)thiophene (100 mg, 0.47 mmol) in dioxane (2 mL) was added bis(pinacolato)diboron (143 mg, 0.56 mmol), PdCi ₂ (dppf).CH ₂ Cl2 (35 mg, 0.05 mmol), KOAc (138 mg, 1 .40 mmol). The resulting reaction mixture was heated to 90 °C in a sealed vessel and stirred for two hours. The reaction mixture was cooled to room temperature then the intermediate from Step A (50 mg, 0.18 mmol) was subsequently added followed by CS2CO3 (1 15 mg, 0.352 mmol) and additional amounts of PdCi2(dppf).CH ₂ Cl2 (35 mg, 0.05 mmol) and dioxane (3 mL). The reaction mixture was again heated to 90 °C and stirred for two hours in a sealed vessel. The reaction was cooled to room temperature and washed with saturated NaHCG ₃ solution. The organic layer was isolated then dried over Mg2S0 ₄ , filtered and cone, into a brown residue which was purified via silica gel chromatography (0-7% 2M NH ₃ / eOH in DCM) to provide the title compound (45 mg, 30%). MS (ESI): mass calcd. for C16H15F2N3OS, 335.3; m/z found, 335.9 [M+H]+. Ή NMR (500 MHz, CDCI ₃ ) δ 8.76 - 8.71 (d, J = 2.0 Hz, 1 H), 7.71 - 7.66 (m, 1 H), 7.37 - 7.33 (d, J = 3.3 Hz, 1 H), 7.28 - 7.23 (m, 2H), 6.97 - 6.72 (m, 2H), 4.96 - 4.89 (s, 2H), 3.14 - 3.09 (s, 3H), 3.04 - 2.97 (s, 3H).

BIOLOGICAL ASSAYS

Inhibition of Specific Binding to the Rat NR1/NR2B Receptor

The assay depends on the binding of a tracer to the GiuN2B subunit- containing NMDA receptors and the ability of the test compounds to displace such binding. 3-[ ³ H] 1 -(azetidin-1 -yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone is a high-affinity GiuN2B-selective antagonist, which binds to the Ifenprodil binding site located at the interphase between GluN1 and GluN2B subunits. Alternatively, The assay measures binding affinity for !igands that compete for the Ifenprodil binding site in the native NMDA receptors from adult rat cortical membranes.

In brief, rat adult cortex is homogenized in the assay buffer (50 m Tris; pH 7.4), The resulting cortical membranes containing native NMDA receptors are purified by centrifugation and extensively washed, then re-suspended in the assay buffer. The test compounds, tracer and membranes are mixed together and incubated with shaking for 2 hours at room temperature to reach binding equilibrium. Non-specific binding of the tracer is determined by pre-incubation of brain membranes with 10 μΜ of CP 101 ,606. Following the incubation, the bound and unbound tracer is separated by filtration with ceil harvester and GF/B filter plates (PerkinElmer) soaked with polyethyienimine.

The extent of binding is measured by counting [3H] radioactivity retained on the filters plates with liquid scintillator counter. Binding affinity (equilibrium dissociation constant Ki) for the test compounds is determined by fitting experimental data with the following model

logEC5o ^::: iog(10 ^A logKi ^* (1 +[Radioiigand]/HotKd)) and Y=Bottom + (Top- Bottom )/(1 +10 ^A (X-LogECso)) where [Radioligand] is the concentration of the tracer, HotKdNM is the equilibrium dissociation constant of the tracer, Top and Bottom are the curve plateaus in the units of Y axis.

HNR2BC: Effects of Test Articles on Cloned Human NR1/NR2B Ion Channels Expressed in Mammalian Cells

NMDA receptors are ion channels that are highly permeable to Ca ²⁺ ions, rendering it possible to monitor NMDA receptor function using cell-based calcium flux assay. In this assay, co-agonists glutamate and glycine are added to ceils heferologously expressing human GluN1/ GluN2B NMDA receptors to initiate cellular Ca ^2÷ influx. The time course of the changes in intracellular calcium is measured using a fluorescent dye and a FLIPR

(Fluorometric Imaging Plate Reader) device.

Twenty four hours before measurements, the expression of the NMDA receptors in the stable ceil line is induced with Tet-On inducible system in the presence of a non-selective NMDA receptor blocker. On the day of the experiment, cell culture media is carefully washed and the cells are loaded with Calcium 5 Dye Kit (Molecular Devices) in dye loading buffer containing 137 mM NaCi, 4 mM KCi, 2 mM CaCI ₂ , 0.5 mM MgCI ₂ , 10 mM HEPES and 5 mM D-giucose; pH 7.4. After 1 h incubation at the room temperature, the dye is washed away with the assay buffer (137 mM NaCi, 4 mM KCI, 2 mM CaCk, 0.01 mM EDTA, 10 mM HEPES and 5 mM D-glucose; pH 7.4) In the FLIPR TETRA reader, various concentrations of the test compounds are added to the cells for 5 min while fluorescence is monitored to detect potential agonist activity. Next, co-agonists, glutamate and glycine are added for another 5 minutes. The concentration of glutamate corresponding to -ECeo is used to maximize the assay's signal window and ability to detect NMDA receptor antagonists and negative ailosteric modulators. A saturating concentration (10 μΜ) of glycine is also present in the assay. A non-selective NMDA receptor antagonist, (+)MK-801 is used as a positive control for antagonist activity. The fluorescent signal in the presence of test compounds is quantified and normalized to the signal defined by the appropriate control wells.

Table 5. Example Compound Name pICso #

1 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-N- cyc!opropyl-acetam ide; 6.5

2 2-[3~Chtoro-6~(4-fluorophenyl)pyrrolo[3 _! 2-b]pyridin~1 - yl]-N-cyclopropyl-acetamide; 6.9

3 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(4- f!uoropheny!)pyrrolo[3,2-b]pyridin-1 -y!]eihanone; 7.6

4 2-(3~Chloro-6~phenyl-pyrrolo[3,2~b]pyridin-1 -yl)-1 - pyrrolidin-1 -yl-ethanone; 7.3

5 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 - morpholino-ethanone; 6.7

6 1 -(Azetidin-1 -yl)-2-(3-chloro-6-phenyl-pyrrolo[3,2- b]pyridin-1 -yi)eihanone; 7.3

7 2-[3-Chloro-6-(4-fiuorophenyl)pyrroio[3 _! 2-b]pyridin-1 - yl]-1 -morpholino-ethanone; 6.8

8 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.5

9 2-[3-Chloro-6-(4-fiuorophenyl)pyrroio[3 _i 2-b]pyridin-1 - yl]-1 -pyrrolidin-1 -yl-ethanone; 7.2

10 2-[3-Chioro-6-(m-tolyi)pyrrolo[3,2-b]pyridin-1 -yi]-N- cyclopropyi-acetam ide; 7.3

1 1 1 -(Azetidin-1 -yl)-2-(3-bromo-6-phenyl-pyrrolo[3,2- b]pyridin-1 -yl)ethanone; 7.6

12 2-[3-Chioro-6-(m-toiyl)pyrrolo[3,2-b]pyridin-1 -yi]-1 - pyrrolidin-1 -yl-ethanone; 7.4

13 2-[3-Chloro-8-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yi]-1 - morpholino-ethanone; 7.3 Example Compound Name pICso #

14 2-(3-Bromo-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-N- cyc!opropyl-acetam ide; 6.9

15 2-(3-Bromo-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 - pyrrolidin-1 -yl-ethanone; 7.4

16 2-(3-Bromo-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 - morpholino-eihanone; 7.1

17 2-[3-Bromo-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yl]-N-cyclopropyi-acetamide; 7.3

18 1 -(Azetidin-1 -yl)-2-[3-bromo-6-(4- fluorophenyl)pyrro!o[3,2-b]pyrid!n-1 -yl]ethanone; 7.7

19 2-[3-Bromo-6-(4-f!uorophenyl)pyrrolo[3 _! 2-b]pyridin-1 - yl]-1 -pyrrolidin-1 -yl-ethanone; 7.5

20 2-[3-Bromo-6-(4-fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 - yl]-1 -morpholino-eihanone; 7.3

21 2-[3-Bromo-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-N- cyclopropyl-acetam ide; 7.4

1 -(Azetidin-1 -yl)-2-[3-bromo-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.6

23 2-[3-Bromo-6-(m-iolyi)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrrolidin-1 ~yl-ethanone; 7.3

24 2-[3-Bromo-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - morpholino-ethanone; 7.0

25 2-[3-Chioro-6-(4-fluoro-3-methyi-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 ~(3,3-difluoroazetidin-1 -yl)ethanone; 7.1

26 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-fiuoroazetidin-1 -yl)ethanone; 7.4 Example Compound Name pICso #

27 2-[6-(4-Fluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin- 1 -yl]-1 -pyrrolidin-1 -y!-ethanone; 7.3

28 2-[8~(4-Fluorophenyl)~3-methyl~pyrrolo[3,2-b]pyridin~

1 -yl]-1 -morpholino-ethanone; 6.7

29 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3,4- difluorophenyl)pyrrolo[3,2-b]pyridin-1 -y!]eihanone; 7.7

30 2-[3-Ch!oro~6-(3,4-difiuorophenyl)pyrro!o[3,2~

b]pyridin-1 -yl]-1 -(3-fluoroazetidin-1 -yl)etbanone; 7.7

31 2-[6-(4-Fluorophenyl)-2-methyl-pyrrolo[3,2-b]pyridin- 1 -yl]-1 -morpholino-ethanone; 5.5

32 N-Cyc!opropyl-2-[6-(4-fluoropheny!)-3-meihyl- pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.4

33 1 -(Azetidin-1 -yl)-2-[6-(4-fluorophenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.2

34 2-[3-Ch!oro-6-(3,4-difluorophenyl)pyrro!o[3,2- b]pyridin-1 -yl]-1 ~(3,3-difluoroazetidin-1 -yl)ethanone; 7.8

35 2-[3-Chloro-8-[4-fluoro-3-

(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]-1 - 6.7

(3~fluoroazetidin~1 -yl)ethanone;

36 2-[3-Chloro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin~1 -yl]-1 -(3,3~difluoroazetidin~1 ~yl)ethanone; 7.0

37 2-[8-(4-Fluorophenyi)-2-methyl-pyrrolo[3,2-b]pyridin- 1 -yl]-1 -pyrrolidin-1 -yl-ethanone; 6.0

38 N-Cyclopropyl-2-[6-(4-fluorophenyl)-2-methyl- pyrroiop^-bjpyridin-l -yljacetamide; 5.3

39 2-[3-Chloro-8-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-fiuoroazetidin-1 -yl)ethanone; 7.5 Example Compound Name pICso #

40 2-[3-ChloiO-6-[4-fluoro-3-

(irifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 -y!]-1 - 6.3 (3,3-difluoroazetidin-1 -yl)ethanone;

41 1 ~(Azeiidin~1 -yl)-2-[2-methyl-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.6

42 2-(2-Methyl-6-phenyl-pyrrolo[3,2-bJpyridin-1 -yl)-1 - pyrrolidin-1 -y!-ethanone; 5.6

43 N-Cyclopropyl~2-(2-methyl-6-phenyl-pyrrolo[3 _! 2- b]pyridin-1 -yl)acetamide; NT

44 2-[2-Methyi-8-(m-iolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrro!idin-1 -yl-eihanone; 6.7

45 2-[2-!Vlethyl-6-(m-io!yl)pyrro!o[3,2-b]pyridin-1 -yl]-1 - morpholino-eihanone; 6.3

46 1 -(Azetidin-1 -yl)-2-[6-(4-fluorophenyl)-2-methyl- pyrrolo[3,2-b]pyridin-1 -yijethanone; 6.3

47 1 -(Azetidin-1 -yl)-2-(2-methyi-8-phenyl-pyrrolo[3,2- bjpyridin-1 ~yi)ethanone; 7.1

48 2-[3-Chloro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -ylj-1 -(3-fiuoroazetidin-1 -yHethanone; 6.2

49 2-[3-Chloro-6-(3,4,5-trifluorophenyl)pyrro!o[3,2- b]pyridin~1 -ylj-1 -(3,3~difluoroazetidin~1 ~yi)ethanone; 6.7

50 2-[3-Chloro-6-(2,3,4-trifluorophenyl)pyrrolo[3,2- bjpyridin-1 -ylj-1 -(3,3-difluoroazetidin-l -yl)eihanone; 7.4

51 N-Cyclopropy!-2-[2-methyl-6-(m-to!yl)pyrro!o[3,2- bjpyridin-1 -yijacetamide; 7.2

52 2-(2-Methyl-6-phenyl-pyrrolo[3,2-bJpyridin-1 -yl)-1 - morpholino-eihanone; 5.9 Example Compound Name pICso #

53 2-[3-Chloro-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -

(3,3-dif!uoroazetidin-1 -y!)ethanone; 5.3

54 2-[3-Chloro-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 ~(3~

fluoroazeiidin-1 -yl)ethanone; 7.2

55 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 - (3,3-difluoroazeiidin-1 -yl)eihanone; 7.5

56 2-(3-Chloro-6-phenyl-pyrrolo[3,2~b]pyridin-1 -yl)-1 -(3- fluoroazetidin-1 -yl)eihanone; 7.3

57 2-[3-Chioro-6-(4-fluorophenyl)pyrroio[3,2-b]pyridin-1 - yl]-1 ~(3,3~difluoroazetidin-1 -y!)ethanone; 7.5

58 2-[3-Chloro-6-(4-f!uoropheny!)pyrrolo[3,2-b]pyridin-1 - yl]-1 -(3-fluoroazetidin-1 -yl)eihanone; 7.6

59 3-[[6-(4-Fluoro-2-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]methyl]-5-methyl-isoxazole; 7.4

60 5-Methyl-3-[[6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yl]methyl]isoxazole; 7.0

61 5-Methyl-3-[[6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yljmethyijisoxazo!e irifluoroacetate salt; 6.4

62 5-!Vleihy!-3-[[6-(o-io!yl)pyrro!o[3,2-b]pyridin-1 - yljmethyljisoxazole trifluoroacetate salt; 6.9

63 3-[[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-

1 -yl]methyi]-5-methyl-isoxazole trifluoroacetate salt; 6.7

64 3-[[6-(3,5-Difluorophenyl)pyrro!o[3,2-b]pyndin-1 - yl]methyl]~5-methyl~isoxazole trifluoroacetate salt; 7.2

65 3-[[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yl]methyi]-5-methyl-isoxazole trifluoroacetate salt; 7.1 Example Compound Name pICso #

66 N-Cyclobutyl-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide 6.7 trifiuoroacetate salt;

67 2-[6~(4-Fluoro-3~meihyl-phenyl)pyrrolo[3,2-b]pyridin~

1 -ylj-1 -pyrrolidin-1 -yl-ethanone trifiuoroacetate salt; 5.3

68 1 -(Azetidin-1 -yl)-2-[3-bromo-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-bjpyridin-1 -yljethanone; 7.4

69 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-bjpyridin-1 -yljethanone; 7.6

70 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]acetic acid; 7.3

71 1 -(Azetidin-1 -yl)-2-[6-(2-f!uoropheny!)pyrrolo[3,2- b]pyridin-1 -yljethanone; 5.1

72 1 -(Azetidin-1 -yl)-2-[6-(3-fluorophenyi)pyrrolo[3,2- b]pyridin-1 -yljethanone; 6.6

73 1 -(Azetidin-1 -yl)-2-[6-(p-to!yl)pyrro!o[3,2-b]pyridin-1 - yljethanone; 7.4

74 1 -(Azetidin-1 -yl)-2-[6-(3-ethylphenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone; 6.7

75 N-Cyciopropyl-2-[6-(2-fluoropheny!)pyrrolo[3,2- b]pyridin~1 -yljacetamide; 7.3

76 N-Cyclopropyl-2-[6-(3-fluorophenyl)pyrrolo[3,2- bjpyridin-1 -yljacetamide; 6.0

77 N-Cyclopropyi-2-[6-(p-to!yl)pyrrolo[3,2-bjpyridin-1 - yljacetamide; 6.6

78 2-(6-Phenylpyrrolo[3,2-b]pyridin-1 -yl)-1 -pyrrolidin-1 - yl-ethanone; 5.8 Example Compound Name pICso #

79 2-[6-(2-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrro!idin-1 -yl-eihanone; 7.1

80 2-[8~(4-Fluorophenyl)pyrroto[3,2-b]pyridin~1 -y!]~1 - pyrrolidin-1 -yl-ethanone; 6.5

81 2-[6-(m-Tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-

1 -y!-eihanone; 6.5

82 2-[6-(p-Tolyl)pyrro!o[3,2~b]pyridin-1 -yl]-1 -pyrrolidin-1 - yl-ethanone; 7.2

83 2-[6-(3-Ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrroiidin-1 -yl-eihanone; 6.6

84 2-[6-(3-Fiuoropheny!)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrrolidin-1 -yl-ethanone; 7.1

85 1 -Morpholino-2-(6-phenylpyrrolo[3,2-b]pyridin-1 - yl)ethanone; 7.2

86 2-[6-(2-Fluorophenyl)pyrro!o[3,2-b]pyridin-1 -yl]-1 - morphoiino-ethanone; 6.3

87 2-[6-(3-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - morphoiino-ethanone; 6.0

88 2-[6-(4-Fiuorophenyl)pyrrolo[3,2-b]pyridin-1 -y!]-1 - morphoiino-ethanone; 6.6

89 1 -Morphoiino-2-[8-(m-toiyl)pyrrolo[3,2-b]pyridin-1 - yljethanone; 6.7

90 1 -Morpholino-2-[6-(p-tolyl)pyrrolo[3,2-b]pyridin-1 - yljethanone; 7.2

91 2-[6-(3-Ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - morphoiino-ethanone; 5.8 Example Compound Name pICso #

92 2-[3-Fluoro-6-(4-fluoro-3-meihyl-phenyl)pyrrolo[3,2- b]pyridin-1 -y!]-N,N-dimeihyi~acetamide; 6.9

93 2-[8~(3,4~Difluorophenyl)~3-fluoro~pyrrolo[3 _! 2~

b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.4

94 2-[3-Fluoro-6-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.2

95 2-[6-[3-(Difluoromethyl)phenyl]-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.4

96 2-[3-Fluoro-6-(4-meibyl-2-ihienyl)pyrrolo[3,2- b]pyridin-1 -y!]-N,N-dimeihyi~acetamide; 7.3

97 2-[6-(5-Ch!oro-2-thieny!)-3-fluoro-pyrro!o[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.2

98 2-[3-Fluoro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yl]-N,N-dimeihy!-aceiamide; 7.3

99 N-Cyclopropy!-2-[6-[5-(irifluoromethyl)-3- pyridyl]pyrrolo[3,2~b]pyridin~1 -yl]aceiamide; 6.2

100 N-Cyclopropyl-2-[6-(3,4-difluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijacetamide; 6.0

101 N-Cyc!opropyl-2-[6-[4-fluoro-3-

(trifluoromeihy^phenyljpyrrotop^-bjpyridin-l - 6.7 y!jacetamide;

102 1 -(Azeiidin-1 -yl)-2-[6-[5-(trifluoromethyl)-3- pyridyl]pyrro!o[3,2-b]pyridin-1 -yl]ethanone; 6.4

103 1 -(Azeiidin-1 -yl)-2-[6-(3,4-difluorophenyi)pyrro!o[3,2- b]pyridin-1 -yijeihanone; 6.6

104 1 -(Azetidin-1 -yl)-2-[6-[4-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.5 yljethanone; Example Compound Name pICso #

105 2-[6-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yl]-1 -pyrro!idin-1 -y!-eihanone; 7.4

106 1 -(3,3-Difiuoroazetidin-1 ~yl)~2-[6~[4~fluoro~3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 6.5 yljeihanone;

107 2-[6-(3,4-Difiuorophenyl)pyrrolo[3,2-b]pyrid!n-1 -yl]-1 - morpholino-eihanone; 6.8

108 2-[6-[4-F!uoro-3-(irifluoromethyl)pheny!]pyrrolo[3,2- b]pyridin-1 -yl]-1 -morpholino-eihanone; 6.9

109 1 -(Azetidin-1 -yl)-2-[6-[2-(trifluoromethyl)-4- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.8

1 10 N-Cyc!opropyl-2-[6-[2-(trif!uoromeihy!)-4- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.6

1 1 1 N-Cyclopropyl-2-[6-[6-(trifluoromethyl)-2- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.4

1 12 1 -(Azetidin-1 -yl)-2-[6-(6-methyl-3-pyridyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 6.3

1 13 5-[1 -[2-( Azetidin-1 -yl)-2-oxo-ethyl]pyrrolo[3,2- b]pyridin-6-yi]pyridine-2-carbonitrile; 5.3

1 14 6-(3,4-Difluorophenyl)-1 -(pyrimidin-5- ylmethyl)pyrrolo[3,2-b]pyridine; <5

1 15 6-(3,4-Difluorophenyl)-1 -[(5-fiuoropyrimidin-2- yl)methyl]pyrrolo[3,2-b]pyridine; 6.5

1 16 Cyc!obutyl-[6-(3,4-difluorophenyl)pyrroio[3 _! 2- b]pyridin-1 -yl]methanone; 6.1

1 17 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-[6-(trifluoromethyl)-

2-pyridyl]pyrro!o[3,2-b]pyridin-1 -yi]ethanone; 5.3 Example Compound Name pICso # O C 1 -(Azetidin-1 -yl)-2-[6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.0

1 19 2-Cyclopropyi-1 ~[6~(3,4~difluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.3

120 1 -Pyrrolidin-1 -yl-2-[6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone; 6.2

121 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[6-(3,5- difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone; 7.2

122 2-[6-(3,5-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrro!idin-1 -yl-ethanone; 7.4

123 1 -Pyrrolidin-1 -yl-2-[6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone; 7.7

124 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone; 7.5

125 2-[6-(3,5-Difiuorophenyl)pyrrolo[3,2-bjpyridin-1 -y!j-1 - morpholino-ethanone; 7.5

126 1 -Morpholino-2-[6-(2,3,4-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.0

127 1 -Morpholino-2-[6-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin~1 -yijethanone; 6.8

128 2-[8-(3,4-Difiuorophenyl)pyrrolo[3,2-bjpyrid!n-1 -ylj-1 - (3-fiuoroazetidin-1 -yl)ethanone; 7.2

129 2-[6-(3,5-Difiuorophenyl)pyrrolo[3,2-bjpyridin-1 -ylj-1 - (3-fiuoroazetidin-1 ~yl)ethanone; 7.6

130 6-(4-Methyl-2-thienyl)-1 -(pyridazin-3- ylmethyl)pyrrolo[3,2-bjpyridine; 7.7 Example Compound Name pICso #

131 6-(3,4-Difluorophenyl)-1 -(pyridazin-3- ylmethy!)pyrroio[3,2-b]pyridine; 6.9

132 2-[6~(4-Methyl~2-ihienyl)pyrroio[3,2-b]pyridin~1 -yl]-1 - morpholino-ethanone; 6.9

133 1 -(Azeiidin-1 -yl)-2-[8-(2,4-difluorophenyl)pyrroio[3,2- b]pyridin-1 -yljethanone; 7.1

134 1 -(Azeiidin-1 -yl)-2-[6-(2,3-difluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone; 7.5

135 1 -(Azetidin-1 -yl)-2-[6-(2,5-difluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone; 7.4

136 1 -Cyciopropyl-2-[6-(3,4-dif!uoropheny!)-3-fiuoro- pyrroto[3,2-bjpyridin-1 -yljethanone; 7.2

137 6-(4-Methyl-2-thienyl)-1 -[[5-(trifluoromethyl)-2- furyl]methyl]pyrrolo[3,2-b]pyridine; 7.7

138 6-(3,4-Dif!uorophenyl)-1 -[[5-(trif!uoromethyl)-2- furyijmethyljpyrrolo[3,2~bjpyridine; NT

139 N,N-Dimethyl-2-[6-(4-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yijacetamide; NT

140 1 -[6-(3,4-Difiuoropheny!)pyrrolo[3,2-bjpyridin-1 -y!j- 3,3~dimethyl-butan~2-one; 7.5

141 1 -[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-

1 -ylj-3,3-dimethyl-bulan-2-one; 6.4

142 1 -[6-(3,5-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -ylj- 3,3-dimethyl~butan-2~one; 6.3

143 3,3-Dimethyl-1 -[6-(4-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yijbutan-2-one; 6.1 Example Compound Name pICso #

144 1 -[6-[3-(Difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-

1 -yl]-3,3-dimeihy!-buian-2-one; 5.7

145 1 -[6~(3-Ethyiphenyl)pyrrolo[3,2-b]pyridin-1 ~yi]~3,3~

dimetbyl-buian-2-one; 6.3

146 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 6.0

147 2-[3-Chloro-6-(3,4-difluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.3

148 2-[3-Chloro-6-(3,5-difluorophenyl)pyrrolo[3,2- b]pyndin-1 -y!]-N,N-dimeihy!-acetamide; 7.3

149 2-[3-Cbloro-6-(4-meihy!-2-tbieny!)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.3

150 2-[3-Chloro-6-[3-(difluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.3

151 2-[3-Ch!oro-6-(3-etbylpheny!)pyrrolo[3,2-b]pyridin-1 - yl]-N,N-dimethyl-acetamide; 7.1

152 2-[3-Chioro-6-(3,4,5-irifiuorophenyi)pyrrolo[3,2- b]pyridin-1 -yi]-N,N-dimethyl-acetamide; 7.0

153 N-Cyc!opropyl-2-[6-(4-methyl-2-thieny!)pyrro!o[3,2- b]pyridin~1 -yl]aceiamide trifiuoroacetate salt; 7.2

154 N-Cyclopropyl-2-[6-(2,3-dimethylphenyl)pyrrolo[3,2- b]pyridin-1 -yl]acetamide trifiuoroacetate salt; 6.4

155 N-Cyciopropyi-2-[6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yljacetamide trifiuoroacetate salt; 6.6

156 N-Cyciopropyi-2-[6-(3,4-dichiorophenyi)pyrrolo[3,2- b]pyridin-1 -yi]acetamide trifiuoroacetate salt; 6.7 Example Compound Name pICso #

157 N-Cyclopropyl-2-[6-[2-methyl-3-

(irifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 - 6.6 yljacetamide trifluoroacetate salt;

158 N~Cyclopropyi-2~(6-phenylpyrrolo[3,2-b]pyridin-1 ~

yl)acetamide trifluoroacetate salt; 6.2

159 N-Cyclopropyl-2-[6-(4-fluoro-2,3-dimethyl- phenyl)pyrrolo[3,2-bjpyridin-1 ~yljacetamide 6.6 trifluoroacetate salt;

160 N-Cyclopropyl-2-[6-(o-tolyl)pyrrolo[3,2-b]pyridin-1 - yljacetamide; 6.7

161 N-Cyclopropyi-2-[6-(4-fluoro-2-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide 6.7 trifluoroacetate salt;

162 1 -(Azetidin-1 -yl)-2-[6-(o-tolyi)pyrroio[3,2-b]pyridin-1 - yljethanone trifluoroacetate salt; 7.0

163 1 -(Azetidin-1 -yl)-2-[6-(4-fluoro-2-methyl- phenyl)pyrrolo[3,2-bjpyridin-1 -yljethanone 7.1 trifluoroacetate salt;

164 1 -(Azetidin-1 -yl)-2-[6-(4-fluoro-2,3-dimethyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone 7.2 trifluoroacetate salt;

165 1 -(Azetidin-1 -yl)-2-[6-(2,3- dimethylphenyi)pyrrolo[3,2-b]pyridin-1 -yljethanone 7.2 trifluoroacetate salt;

166 1 -(Azetidin-1 -yl)-2-[6-[3-

(trifluoromethy^phenyijpyrroiop^-bjpyridin-l - 6.9 yljethanone trifluoroacetate salt;

167 1 -(Azetidin-1 -yl)-2-[6-[2-methyl-3-

(trifluoromethyi)phenyljpyrroio[3,2-bjpyridin-1 - 7.4 yljethanone trifluoroacetate salt;

168 N-Cyciopropyi-2-[6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijacetamide; 6.6

169 1 -(Azetidin-1 -yl)-2-[6-(4-fluoro-3-methyl-phenyl)-3- methyl-pyrrolo[3,2-bjpyridin-1 -yljethanone 6.7 trifluoroacetate salt; Example Compound Name pICso #

170 1 -Buiyl-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- bjpyridine trifluoroacetaie salt; 6.5

171 6-(4-Fluoro~3-methyl~phenyl)-1 -isopeniyl~pyrrolo[3,2- bjpyridine trifluoroaceiate salt; 6.7

172 6-(4-Fluoro-3-methyl-phenyl)-1 -(3- pyridy!methyl)pyrro!o[3,2-b]pyridine trif!uoroacetate 6.1 salt

173 1 -(Cyclobutylmethyl)-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridine trifluoroacetate salt; 7.2

174 1 -(Cyclopropylmethyl)-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3 _! 2-b]pyridine trifluoroacetate salt; 6.8

175 2-[6-(4-F!uoro-3-methyl-pheny!)pyrrolo[3,2-b]pyridin- 1 -yl]-N,N-dimethyl-acetamide trifluoroacetate salt; 6.3

176 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- bjpyridin-1 -yl]-N-cyclopropyl-acetam ide 7.5 trifluoroacetate salt;

177 6-(4-Fluoro-3-methyl-phenyl)-1 -(2- pyridylmethyl)pyrrolo[3,2-b]pyridine trifluoroacetate 7.5 salt;

178 (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 -

(tetrahydrofuran-3-ylmethyl)pyrroio[3,2-b]pyridine 6.5 trifluoroacetate salt;

179 6-(4-Fluoro-3-methyl-phenyi)-1 -(4- pyridylmethy pyrroiop^-bjpyridine trifluoroacetate 7.3 salt;

180 (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 -(oxiran-2- ylmethyl)pyrrolo[3,2-b]pyridine trifluoroacetate salt; 6.1

181 6-(4-Fluoro-3-methyl-phenyl)-1 -(2-pyrazol-1 - ylethyi)pyrrolo[3,2~b]pyridine trifluoroacetate salt; 6.1

182 1 -(Azetidin-1 -yl)-2-[6-(5-chloro-2-thienyl)-3-fluoro- pyrroio[3,2-b]pyridin-1 -yl]ethanone; 5.4 Example Compound Name pICso #

183 6-(4-Fluoro-3-methyl-phenyl)-1 -(pyrimidin-2- ylmethyl)pyrrolo[3,2-b]pyridine trif!uoroacetate salt; 7.5

184 (R/S)~6-(4~Fluoro~3-methyl~phenyl)-1 ~(oxetan~2- ylmethyl)pyrrolo[3,2-b]pyridine trifluoroacetate salt; 6.3

185 1 -(3,3-Difluoroazetidin-1 -yl)-2-[3-fluoro-6-(4-fluoro-3- methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.0

186 1 -Cyciopropyi~2-[6-(4-fiuoro-3-rnetbyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 7.4 trifluoroacetate salt;

187 1 -[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-

1 -yl]-3-methy!-butan-2-one trifluoroacetate salt; 7.3

188 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]-1 -(4-hydroxy-1 -piperidyl)ethanone 7.3 trifluoroacetate salt;

189 (R/S)-1 -(3-Azabicyclo[3.1 .0]hexan-3-yl)-2-[6-(4- fluoro-3-methyi-phenyi)pyrrolo[3,2-b]pyridin-1 - 6.9 yljethanone trifluoroacetate salt;

190 2-[6-(4-Fluoro-3-methyi-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]-1 ~(4-methoxy-1 ~piperidyl)ethanone 6.6 trifluoroacetate salt;

191 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]-1 -(4-f luoro-1 -piperidyl)ethanone trifluoroacetate 6.5 salt;

192 2-[6-(4-Fiuoro-3-methyl-phenyi)pyrrolo[3,2-b]pyridin- 1 -yl]-1 -[4~(fluoromethyi)~1 -piperidyijethanone 7.1 trifluoroacetate salt;

193 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -y|]-1 -(1 -piperidyl)ethanone trifluoroacetate salt; 6.1

194 (R/S)-2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 ~yi]~1 ~(2-methylmorphoiin-4~yi)ethanone 6.8 trifluoroacetate salt;

195 (R/S)-2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -[3-(trifluoromethyl)-1 - 6.4 piperidyijethanone trifluoroacetate salt; Example Compound Name pICso #

196 (R/S)-1 -(2-Ethylpyrrolidin-1 -yl)-2-[6-(4-fluoro-3- methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 5.9 trifiuoroacetate salt;

197 1 -(2,2-Dimethylmorpholin-4~yl)-2~[6-(4~fluoro-3~

methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 5.8 trifiuoroacetate salt;

198 (R/S)-2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-methoxypyrrolidin-1 -yl)ethanone 6.0 trifiuoroacetate salt;

199 (R/S)-2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yij-1 -(3-fluoro-1 -piperidyi)ethanone 6.7 trifiuoroacetate salt;

200 1 -(2,2-Dimethylpyrrolidin-1 -yl)-2-[6-(4-fluoro-3- methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 6.6 trifiuoroacetate salt;

201 2-[6-(4-Fiuoro-3-methyi-phenyi)pyrrolo[3,2-b]pyridin- -yl]-1 -[(3R)-3-fluoropyrroiidin-1 -yljethanone 5.4 trifiuoroacetate salt;

202 2-[6-(4-Fiuorophenyl)pyrroio[3,2-b]pyrid!n-1 -yl]-1 -(3- hydroxy-3-methyl-azetidin-1 -yljethanone; 6.9

203 2-[6-(4-Fiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yi]-1 -[3- hydroxy-3-(trifluoromethyl)azetidin-1 -yljethanone; 6.4

204 1 ~(3-Fluoroazetidin-1 -yl)-2-[6-(4- fluorophenyl)pyrroio[3,2-b]pyridin-1 -yljethanone; 5.8

205 N-Cyciopropyi-2-[6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N-methyl-acetamide; 7.3

206 2-[6-(4-Fiuorophenyl)pyrroio[3,2-b]pyrid!n-1 -yl]-1 -[3- (hydroxymethyl)azetidin-l -yljethanone; 6.5

207 2-[6-(4-Fiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yi]-1 -(3- methoxyazetidin~1 -yljethanone; 6.5

208 1 -(5-Azaspiro[2.3]hexan-5-yi)-2-[6-(4-fluoro-3- methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone 6.5 trifiuoroacetate salt; Example Compound Name pICso #

209 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]-1 -(4-hydroxy-4-methy!-1 -piperidyl)ethanone 6.7 trifiuoroacetate salt;

210 (R/S)~2-[6-(4-Fluoro~3-methyl~phenyl)pyrrolo[3,2~

b]pyridin-1 -yl]-1 -(3-methylmorpholin-4-yl)ethanone 6.4 trifiuoroacetate salt;

21 1 2-[8-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- hydroxyazetidin-1 -yl)ethanone; 6.4

212 1 -[2-[6-(4-Fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 - yl]acetyl]azetidine-3-carbonitrile; 6.5

213 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(4- fluorophenyl)pyrrolo[3,2-b]pyrid!n-1 -yl]ethanone; 6.2

214 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- meihylazeiidin-1 -yl ethanone; 7.0

215 1 -(3,3-Dimethylazetidin-1 -yl)-2-[6-(4- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.8

216 1 -[2-[6-(4-Fluorophenyl)pyrrolo[3 _! 2-b]pyridin-1 - yl]acetyl]pyrrolidin-3~one trifiuoroacetate salt; 5.9

217 1 -(3,3-Difluoropyrrolidin-1 -yl)-2-[6-(4- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.5

218 (R/S)-2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yl]-1 ~(3-hydroxypyrrolidin~1 -yl)ethanone; 6.4

219 1 -Cyclopropyl-2-[6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yljethanone; 6.3

220 1 -Cyciopropyi-2-(6-phenylpyrrolo[3,2-b]pyridin-1 - yl)ethanone; 7.3

221 1 -Cyciopropyl-2-[6-(3-fiuorophenyi)pyrrolo[3,2- b]pyridin-1 -yljethanone; 7.1 Example Compound Name pICso #

222 1 -Cyclopropyi-2-[6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone; 7.1

223 1 -[8~(4-Fluoro-2,3~dimeihyi-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-3-methyl-butan-2-one; 7.1

224 1 -[6-(3-Ethylphenyl)pyrrolo[3,2-b]pyridiri-1 -yl]-3- meihy!-buian-2-one; 6.4

22*3 1 -[6-(2,3-Dimethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-

3-meihyl-buian-2-one; 7.1

226 2-[8-(4-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-1 - phenyl-eihanone; 6.7

227 1 -(4-Fluorophenyl)-2-[6-(4-f!uoropheny!)pyrro!o[3,2- b]pyridin-1 -yijethanone; 6.1

228 (R/S)-6-(4-Fluorophenyl)-1 -(tetrahydropyran-2- ylmethyl)pyrrolo[3,2-b]pyridine trifluoroacetaie sa!i; 6.2

223 2-[6-(4-Fluorophenyl)pyrro!o[3,2-b]pyridin-1 -yl]-N- isopropyl-acetam ide; 6.3

230 2-[8-(4-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-N- propyl-aceiamide; 5.3

231 (R/S)-2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yl]-IM~(2,2,2~trifiuoro~1 -methyl~eihyi)acetamide; 5.7

232 2-[8-(4-Fiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N-(1 - meihy!cyciopropyl)acetamide; 5.0

233 N-(2-F!uoroeihy!)-2-[6-(4-fluorophenyl)pyrro!o[3,2- b]pyridin-1 -yijacetamide; 4.8

234 2-[8-(4-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-N- isobutyl-acetamide; 5.6 Example Compound Name pICso #

235 5-[[6-(4-Fluoro-3-meihyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]methyl]-3-methyl-1 ,2,4-oxadiazole; 4.9

236 6~(4-Fluoro~3-methyl~phenyl)-1 -[(1 -methylpyrazol-4~

yl)methyl]pyrrolo[3,2-b]pyridine; 6.7

237 N-(Cyclopropylmethyi)-2-[6-(4- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 5.7

238 6-(4-Fluoro-3-methyl-phenyl)-1 -[(1 -methyltriazol-4- yl)methyl]pyrrolo[3,2-b]pyridine; 5.5

239 5-[[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]methyl]-3-methyl-1 ,2,4-oxadiazole; 6.8

240 3-Chloro-6-(4-fluoro-3-meihy!-phenyl)-1 -[(1 - methylpyrazol-4-yl)methyl]pyrrolo[3,2-b]pyridine; 6.3

241 2-[3-Chloro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -cyciobutyl-etbanone; 5.3

242 1 -Cyclobuty!-2-[6~(4-fiuoro-3-rnethyl- phenyl)pyrrolo[3,2~b]pyridin-1 ~yl]eihanone; 6.1

243 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[5-(trifluoromethyl)-3- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]ethanone 7.0 trifluoroacetate salt;

244 2-[3-Chloro-6-[5-(trifluoromethyl)-3- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]-N-cyclopropyl- 6.2 acetamide trifluoroacetate salt;

245 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[6-(trifluoromethyl)-2- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.4

246 2-[3-Ch!oro-6-[6-(trifluoromethyl)-2- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]-N-cyclopropyl- 7.0 acetamide;

247 2-[3-Chioro-6-[6-(trifluoromethyl)-2- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]-1 -{3-fiuoroazetidin- 6.5 1 -yl)ethanone; Example Compound Name pICso #

248 N-Cyclopropyi-2-[6-(3,4,5-irifluorophenyl)pyrrolo[3 _i 2- b]pyridin-1 -y!jacetamide; 7.2

249 N~Cyclopropyi-2~[6-(2,3,4-trifluorophenyl)pyrrolo[3 _! 2~

b]pyridin-1 -yijacetamide; 7.1

250 N-Cyclopropyl-2-[6-[3-

(difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 6.6 yljacetamide;

251 N-Benzy!-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin- 1 -yijacetamide; 7.3

2-[[6-(4-Fluoro-3-meihyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]methyi]oxazole; 5.3

2-[6-(4-F!uoropheny!)pyrrolo[3,2-b]pyridin-1 -y!]-N-(2- hydroxyethyl)acetam ide; 7.1

254 2-[6-(4-Fiuorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N-(2- meihoxyethyl)acetam ide; 5.9

255 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[6-[2-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 5.4 yljethanone trifluoroacetate salt;

256 1 -(3,3-Difluoroazetidin-l -yl)-2-[6-(3- fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]ethanone 7.1 trifluoroacetate salt;

257 1 -(3,3-Difluoroazetidin-1 -yl)-2-(6-phenylpyrrolo[3,2- b]pyridin~1 -yl)ethanone trifluoroacetate salt; 6.9

258 1 -(3,3-Difiuoroazetidin-1 -yl)-2-[6-(3- ethyiphenyl)pyrroio[3,2-b]pyridin-1 -yl]etharione 6.7 trifluoroacetate salt;

259 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 7.5 trifluoroacetate salt;

260 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.4 yljethanone trifluoroacetate salt; Example Compound Name pICso #

261 1 -(3,3-Difluoroazeiidin-1 -yl)-2-[6-(4-fluoro-2-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 7.3 trifiuoroacetate salt;

262 1 -(3-Fluoroazetidin-1 ~yl)~2-[6-[4~fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.0 yljethanone trifiuoroacetate salt;

263 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(3- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 6.8 trifiuoroacetate salt;

264 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(4-fluoro-2-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 7.2 trifiuoroacetate salt;

265 1 -(3-Fluoroazefidin-1 -yl)-2-[6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.0 yljethanone trifiuoroacetate salt;

266 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -yl]ethanone trifiuoroacetate salt; 6.9

267 1 -(3-Fiuoroazetidin-1 -yl)-2-[6-[2-fluoro-3-

(trifluoromethyl)phenyl]pyrroio[3,2-b]pyridin-1 - 7.4 yljethanone trifiuoroacetate salt;

268 2-[6-(3-Ethylphenyi)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3- fluoroazetidin~1 -yi)ethanone trifiuoroacetate salt; 7.1

269 1 -(3,3-Difluoroazefidin-1 -yl)-2-[6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.2

270 1 -(3-Fluoroazetidin-1 -yl)-2-(6-phenyipyrrolo[3,2- b]pyridin~1 -yi)ethanone; 7.4

271 1 -(3,3-Difiuoroazetidin-1 -yl)-2-[6-(2,4-difluoro-3- methyl-phenyi)-3-fiuoro-pyrrolo[3,2-b]pyridiri-1 - 7.1 yljethanone;

272 (R/S)-1 -[6-(3,5-Difluorophenyl)pyrrolo[3,2-b]pyridin- 1 -yl]-3-methyl-butan-2-ol; 7.6

273 2-[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -y|]-l -{3-hydroxyazetidin-1 -yl)ethanone; 6.0 Example Compound Name pICso #

274 (R/S)-1 -Cyelopropyi-2-[6-(4-fluoro-3-meihyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanol; 7.2

275 (R/S)~2-Cyciopropyl~1 -[6~(4-fluoro~3-methyl~

phenyl)pyrrolo[3,2-b]pyridin-1 -yl]propan-2-ol 6.8 trifiuoroacetate salt;

276 1 -Cyclopropyl-2-[6-(4-fluoro-3-methyl- phenyl)pyrro!o[3,2-b]pyridin-1 -yl]-IM-methoxy- 6.3 ethanimine;

277 1 -(3-F!uoroazetidin-1 -yl)-2-[6-(2-thieny!)pyrrolo[3,2- b]pyridin-1 -yl]ethanone; 5.5

278 1 -Pyrrolidin-1 -yl-2-[6-(2-thienyl)pyrrolo[3,2-b]pyridiri-

1 -yl]ethanone; 6.6

279 1 -(3,3-Difluoroazeiidin-1 -yl)-2-[6-(5-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.6

280 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(5-methyl-2- thieny!)pyrrolo[3,2-b]pyridin-1 -yl]eihanone; 7.5

281 2-[6-(5-Eihyl-2-thieny!)pyrrolo[3,2-b]pyridin-1 -yl]-1 - (3-fluoroazetidin-1 ~yl)ethanone; 7.7

282 2-[6-(5-Ethyl-2-tbienyl)pyrroio[3,2-b]pyridin-1 -yl]-1 - pyrrolidin-1 -yl-ethanone; 7.1

283 2-[6-(5-Meihy!-2-thienyl)pyrrolo[3,2-b]pyridin-1 -y!]-1 - pyrrolidin-1 ~yl-ethanone; 6.7

284 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(5-ethyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]eihanone; 7.0

285 2-[6-(4-Chloro-2-ihienyl)pyrro!o[3,2-b]pyridin-1 -yl]-1 - (3-fiuoroazetidin-1 ~yl)ethanone; 6.8

286 1 -Cyciopropyl-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone oxime 6.8 trifiuoroacetate salt; Example Compound Name pICso #

287 2-[6-(5-Chloro-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrro!idin-1 -yl-eihanone; 6.2

288 2-[8~(4-Chloro~2-ihienyl)pyrroio[3,2-b]pyridin~1 -yl]-1 - pyrrolidin-1 -yl-etbanone; 7.7

289 (R/S)-1 -(2-Cyclopropyl-2-fiuoro-ethyl)-6-(4-fluoro-3- methyl-phenyl)pyrrolo[3,2-b]pyridine; 7.1

290 2-[6-(4-Fluoro~3-methyi~phenyl)pyrrolo[3,2~b]pyridin- 1 -yl]-1 -(3-methoxyazetidin-1 -yl)efhanone; 6.2

291 6-(4-Fluoro-3-methyl-phenyl)-1 -(2- methoxyethyl)pyrrolo[3,2-b]pyridine irif!uoroaceiate 7.1 salt;

202 1 -Cyclobutyl-2-[6-(3-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 5.9

293 2-[6-(4-Fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -

[(3R)-3-fluoropyrrolidin-1 -yijethanone trifluoroacetate 7.5 salt;

294 2-[6-(4-Fluorophenyl)pyrro!o[3,2-b]pyridin-1 -yl]-1 - [(3S)-3~fiuoropyrrolidin~1 -yijethanone trifluoroacetate 6.5 salt;

295 1 -[6-(4-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin-

1 -yl]butan-2-one trifluoroacetate salt; 6.5

296 N-Ethyl-2-[6-(4-fluoro-3-methyi-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N-methyl-acetamide; 7.6

297 N,N-Diethyl-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetaniide; 7.4

298 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 6.3 yljethanone;

299 2-[3-Chioro-8-(m-toiyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - cyciopropyl-ethanone; 7.3 Example Compound Name pICso #

300 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-1 - cyc!opropyl-ethanone; 7.7

301 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.7

302 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(4- fiuorophenyi)pyrrolo[3,2-b]pyridin-1 -y!]eihanone; 7.5

303 1 -(Azetidin-1 -yi)-2-[3-chioro-6-(3 _! 5- dimethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.4

304 2-[3-Fiuoro-6-(4-fluoro-3-meihyl-phenyl)pyrroio[3,2- b]pyridin-1 -yl]-1 -morpho!ino-ethanone; 6.8

305 2-[3-F!uoro-6-(4-f!uoropheny!)pyrrolo[3,2-b]pyridin-1 - yl]-1 -morpholino-ethanone; 7.1

306 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.4

307 1 -(3-F!uoroazetidin-1 -yl)-2-[3-fluoro-6-(4-fluoro-3- methyl-pheny pyrroiois^-bjpyridin-l -yljethanone; 7.4

308 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(4- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.2

309 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(4-methyl-2- thienyi)pyrrolo[3,2~b]pyridin-1 ~yl]ethanone; 6.7

310 2-[6-[3-(Difluoromethyl)phenyl]-3-fluoro-pyrrolo[3,2- bjpyridin-1 -yl]-1 -(3-fluoroazetidin-1 -yl)eihanone; 7.3

31 1 2-[6-(3,4-Difluorophenyl)-3-f!uoro-pyrrolo[3 _! 2- b]pyridin-1 -yl]-1 ~(3-fiuoroazetidin-1 ~yl)ethanone; 7.2

312 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.8 Example Compound Name pICso #

313 2-[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -pyrro!idin-1 -y!-eihanone; 7.7

314 2-[3~Fluoro-6-(4~fluorophenyl)pyrrolo[3,2-b]pyridin-1 ~

yl]-1 -pyrrolidin-1 -yl-ethanone; 7.2

315 2-[3-Fluoro-6-(3,4,5-tr!fluorophenyl)pyrrolo[3,2- bjpyridin-1 -yl]-1 -pyrrolidin-1 -yl-ethanone; 7.1

316 1 -Cyclopropy!-2-[3-f!uoro-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.4

317 1 -Cyclopropyl-2-[3-fluoro-8-(4-methyl-2- thienyl)pyrrolo[3,2~b]pyridin-1 -yl]ethanone; 7.4

318 2-[6-(5-Chloro-2-thienyl)-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yl]-1 -cyclopropyl-ethanone; 7.7

319 1 -Cyclopropyl-2-[3-fluoro-6-(4- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]eihanone; 7.7

320 1 -Cyclopropy!-2-[3-f!uoro-6-(3,4,5- irifluorophenyl)pyrrolo[3,2-b]pyridin-1 ~yl]ethanone; 7.5

321 1 -Cyclopropyl-2-[6-[3-(difluoromethyl)phenyl]-3- fluoro-pyrrolo[3,2-b]pyridin-1 -yl]eihanone; 7.7

322 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(4-methyl-2- thienyl)pyrrolo[3,2~b]pyridin-1 ~yl]ethanone; 7.7

323 1 -(Azetidin-1 -yl)-2-[6-[3-(difluoromethyl)phenyl]-3- fluoro-pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.0

324 1 -[3-Fiuoro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3 _! 2- b]pyridin-1 ~yi]~3~methyl~butan~2-one; 7.0

325 1 -[6-(3-Ethylphenyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 - yl]-3-methyl-butan-2-one; 6.7 Example Compound Name pICso #

326 1 -[6-(3,4-Difluorophenyl)-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yl]-3-methyl-butan-2-one; 6.7

327 1 -[3~Fluoro-6-(3~fluorophenyl)pyrrolo[3,2-b]pyridin-1 - yl]-3-methyl-buian-2-one; 7.2

328 1 -[3-Fluoro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yl]-3-methyl-butan-2-one; 7.2

329 1 -[3-F!uoro-6-(m-io!yl)pyrro!o[3,2-b]pyridin-1 -yl]-3- methyl-butan-2-one; 6.3

330 6-(4-Fluoro-3-meihyl-phenyl)-1 - (methylsulfanylmethyl)pyrrolo[3,2-b]pyridine; 7.2

331 (R/S)-6-(4-Fluoro-3-methyl-phenyl)-1 - (methylsulfinylmethyl)pyrrolo[3,2-b]pyridine; 5.4

332 6-(4-Fluoro-3-methyl-phenyl)-1 - (methylsulfonylmethyl)pyrrolo[3,2-b]pyridine; 5.8

333 1 -[3-Fluoro-6-(4-fluorophenyl)pyrro!o[3,2-b]pyridin-1 - yl]butan-2~one; 5.2

334 1 -[3-Fluoro-6-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yi]butan-2-one; 7.6

335 1 -[3-Fluoro-6-(4-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin~1 -yl]buian-2~one; 7.9

336 1 -[6-(3,4-Difiuorophenyl)-3-fluoro-pyrrolo[3 _i 2- b]pyridin-1 -yl]butan-2-one; 7.7

337 1 -[6-[3-(Difluoromethyl)phenyl]-3-fluoro-pyrrolo[3,2- b]pyridin-1 ~yi]butan~2-one; 7.8

338 1 -[6-(5-Chloro-2-thienyl)-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yi]butan-2-one; 7.8 Example Compound Name pICso #

339 1 -[3-Fluoro-6-(4-methyi-2-ihienyl)pyrrolo[3,2- b]pyridin-1 -y!]butan-2-one; 7.9

340 4-[8~(4-Fluorophenyl)pyrroto[3,2-b]pyridin~1-yl]buian- 2-one; 7.9

341 1 -[3-Fluoro-6-(4-fluorophenyi)pyrrolo[3,2-b]pyridin-1 - y!]-3-meihy!-butan-2-one; 6.0

342 1 -[6-[3-(Difluoromethyl)phenyl]-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yl]-3-methyl-butan-2-one; 7.3

343 1 -[3-Fluoro-6-(4-methyi-2-ihienyl)pyrrolo[3,2- b]pyridin-1 -yl]-3-methyl-butan-2-one; 7.2

344 1 -[3-Fluoro-6-(3,4,5-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]-3-methyl-butan-2-one; 7.3

345 1 -[8-(5-Chloro-2-ihienyl)-3-fluoro-pyrrolo[3 _i 2- b]pyridin-1 -yl]-3-methyl-butan-2-one; 7.5

346 2-[6-(4-Fluoro-3-meihy!-phenyl)pyrro!o[3,2-b]pyridin- 1 -yl]-1 -morpholino-ethanone; 7.4

347 1 -(3-Fluoroazeiidin-1 -yl)-2-[6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1-yi]ethanone; 7.3

348 N-Cyclopropyl-2-[6-(4-fluoro-3-methyl- pheny pyrrolo^^-bjpyridin-l-yljaceiamide; 7.5

349 1 -(Azetidin-1 -yl)-2-[6-(4-fluoro-3-methyl- pheny!)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.5

350 N-Cyclopropy!-2-[6-(3,5-difluorophenyl)pyrrolo[3,2- b]pyridin-1 ~yi]acetamide irifluoroaceiate salt; 7.8

351 N-Cyciopropyi-2-[6-[3-

(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.1 yljacetamide irifluoroaceiate sali; Example Compound Name pICso #

352 N-Cyciopropyi-2-[6-[2-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.4 yljacetamide tnfiuoroacetate salt;

353 1 ~(Azetidin~1 -yl)-2~[6~(4~fluorophenyl)pyrrolo[3,2- b]pyridin-1 -yljethanone; 7.5

354 1 -(Azeiidin-1 -yl)-2-(6-phenylpyrrolo[3,2-b]pyridin-1 - yl)ethanone; 7.5

355 1 -(Azeiidin-1 -yl)-2-[6-(3,5-difluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]ethanone; 7.3

356 1 -(Azeiidin-1 -yl)-2-[6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 - yljethanone tnfiuoroacetate salt; 7.7

357 1 -(Azetidin-1 -yl)-2-[6-(3,4-dich!orophenyl)pyrro!o[3,2- b]pyridin-1 -yljethanone trifluoroacetate salt; 7.7

358 1 -(Azetidin-1 -yl)-2-[6-[2-fluoro-3-

(trifluoromethyl)phenyl]pyrroio[3,2-b]pyridin-1 - 7.4 yljethanone trifluoroacetate salt;

359 1 -(Azetidin-1 -yl)-2-[6-(4-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yljethanone trifluoroacetate salt; 7.5

360 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(4-fluoro-3-methyl- phenyl)pyrrolo[3,2-bjpyridin-1 -yljethanone; 7.5

361 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(3,4- difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone; 7.6

362 1 -(Azetidin-1 -yl)-2-[6-[6-(trifluoromethyl)-2- pyridyl]pyrrolo[3,2-bJpyridin-1 -yljethanone; 7.5

363 1 -(Azetidin-1 -yl)-2-[6-(3,4,5- trifiuorophenyi)pyrrolo[3,2-bjpyridin-1 -yljethanone; 7.1

364 1 -[6-(3,5-Difluorophenyl)pyrrolo[3,2-bJpyridin-1 -yl]-3- methyl-butan-2-one; 7.7 Example Compound Name pICso #

365 1 -Cyclobutyl-2-[6-(4-fluorophenyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone; 7.7

366 N~Cyclopropyi-2~[6-(3~ethylphenyl)pyrrolo[3,2~

b]pyridin-1 -yijacetamide; 7.5

367 2-[6-(3,4-Difiuorophenyl)pyrrolo[3,2-b]pyrid!n-1 -yl]-1 - pyrrolidin-1 -y!-ethanone; 7.3

368 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[6-(4-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.6

369 2-[6-(4-Methyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 - pyrro!idin-1 -yl-eihanone; 7.7

370 1 -(3-Fluoroazeiidin-1 -yl)-2-[6-(4-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.5

371 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.8

372 2-[6-(5-Chloro-2-ihienyl)pyrro!o[3,2-b]pyridin-1 -yl]-1 - (3-fluoroazetidin-1 ~yl)ethanone; 7.8

373 1 -(Azetidin-1 -yl)-2-[6-(5-chloro-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.7

374 2-[3-Chloro-6-(2,3,4-irifluorophenyl)pyrro!o[3,2- b]pyridin~1 -y!]-1 -(3~fluoroazeiidin~1 -yl)ethanone; 7.7

375 N.N-Dimeihyl^-p^S^^-trifluorophenylipyrrolo^^- b]pyridin-1 -yijacetamide; 7.9

376 2-[6-(3,5-Difluorophenyl)pyrro!o[3,2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide; 7.7

377 2-[6-[3-(Difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin- 1 -yl]-N,N-dimethyl-acetamide; 8.0 Example Compound Name pICso #

378 2-[6-(5-Chloro-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-

N,N-dimethyl-acetamide; 8.2

379 2-[8~(3,4~Difluorophenyl)pyrroio[3,2-b]pyridin~1 -yl]~

N,N-dimethyl-acetamide; 7.5

380 1 -(Azetidin-1 -yl)-2-[6-(5-methyl-2-thienyl)pyrroio[3,2- b]pyridin-1 -yljethanone; 8.0

381 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(5-ch!oro-2- thienyl)pyrroio[3,2-bjpyridin-1 -yljethanone; 7.8

382 1 -(Azetidin-1 -yl)-2-[6-(3,4-difluorophenyl)-3-fluoro- pyrroio[3,2-bjpyridin-1 -yljethanone; 7.8

383 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(3 ,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.8

384 2-[3-Chloro-6-(4-fiuorophenyl)pyrroio[3 _! 2-b]pyridin-1 - yl]-1 -cyclopropy!-ethanone; 7.7

385 1 -(Azetidin-1 -yl)-2-[6-(3-thienyl)pyrro!o[3,2-b]pyridin- 1 -yljethanone trifiuoroacetate salt; 7.7

386 N,N-Dimethyl-2-[6-(5-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yi]acetamide trifiuoroacetate salt; 6.4

387 2-[3-Fluoro-6-(2-thienyl)pyrrolo[3,2-b]pyridin-1 -yi]- N,IM~dimethyl-acetamide; 7.2

388 2-[6-(5-Ethyl-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide trifiuoroacetate salt; 6.1

389 1 -(Azetidin-1 -yl)-2-[3-f!uoro-6-(2-thienyl)pyrroio[3,2- b]pyridin-1 -yljethanone trifiuoroacetate salt; 6.8

390 2-[3-Fluoro-6-(5-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 6.5 Example Compound Name pICso #

391 2-[6-(4-Chloro-2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-

Ν,Ν-dimethyl-acetamide trifluoroacetate salt; 7.3

392 1 -(Azeiidin~1 -yl)-2~[6~(5~ethyl~2-ihienyl)pyrroto[3,2- b]pyridin-1 -yl]ethanone trifluoroacetate salt; 7.2

393 2-[6-(5-Ethyl-2-thienyl)-3-fluoro-pyrrolo[3,2-b]pyridin- 1 -yl]-N,N-dimethyl-acetamide; 6.9

394 1 -(Azetidin-1 -yl)-2-[6-(4-chloro-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yl]ethanone trifluoroacetate salt; 6.8

395 1 -(3-Fluoroazefidin-1 -yl)-2-[3-fluoro-6-(2- thienyl)pyrro!o[3,2~b]pyridin-1 -yl]ethanone 7.3 trifluoroacetate salt;

396 2-[6-(4-Ch!oro-2-thienyi)~3-fluora-pyrroio[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 6.3

397 1 -(Azetidin-1 -yl)-2-[6-(4-chloro-2-thienyl)-3-fluoro- pyrroio[3 _! 2-b]pyridin-1 -y!jethanone trifluoroacetate 7.3 salt;

398 2-[6-(5-Ethyl-2-thienyl)-3-fluoro-pyrrolo[3,2-b]pyridin- 1 -yl]-1 ~(3~fiuoroazetidin~1 -yi)ethanone 7.4 trifluoroacetate salt;

399 1 -(Azetidin-1 -yl)-2-[6-(2-thienyl)pyrrolo[3,2-b]pyridin-

1 -yl]ethanone; 6.8

400 N,N-Dimethyl-2-[6-(2-thienyi)pyrroio[3,2-b]pyridin-1 - yljjacetamide; 6.3

401 1 -(Azetidin-1 -yl)-2-[6-(5-ethyl-2-thienyl)-3-fluoro- pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.2

402 1 -(3-F!uoroazetidin-1 -yl)-2-[3-fluoro-6-(5-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone 6.6 trifluoroacetate salt;

403 1 -(Azetidin-1 -yl)-2-[6-(3-chloro-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.0 Example Compound Name pICso #

404 1 -(Azetidin-1 -yl)-2-[6-(2-methylthiazol-5- y!)pyrrolo[3,2-b]pyridin-1 -y!]eihanone; 7.5

405 1 -(Azeiidin~1 -yl)-2-(6-thiazol-5-ylpyrrolo[3,2- b]pyridin-1 -yljethanone; 5.0

406 1 -(Azetidin-1 -yl)-2-[6-(6-fluoro-3-pyridyl)pyrroio[3,2- b]pyridin-1 -yljethanone; NT

407 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(4-methyl-2- thienyl)pyrrolo[3,2-bjpyridin-1 -yljethanone; 5.2

408 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(5-ethyl-2- thienyl)pyrrolo[3,2~bjpyridin-1 -yljethanone; 7.4

409 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(2-thienyl)pyrrolo[3,2- b]pyridin-1 -yljethanone; 6.7

410 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(5-methyl-2- thienyi)pyrrolo[3,2-bjpyridin-1 -yljethanone; 6.5

41 1 2-[6-(4-Fiuorophenyl)pyrro!o[3,2-bjpyridin-1 -ylj-N- methyl-N-(2,2,2-trifluoroethyl)acetamide; 7.6

412 2-[3-Chloro-6-(5-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yij-1 -(3-fluoroazetidin-i -yl)ethanone; 5.1

413 2-[3-Chioro-6-(5-chloro-2-thienyi)pyrro!o[3,2- bjpyridin~1 -yij-1 -(3~fluoroazetidin~1 -yi)ethanone; 7.3

414 2-[3-Chloro-6-(4-chloro-2-thienyl)pyrrolo[3,2- bjpyridin-1 -ylj-N,N-dimethyl-acetamide; 7.4

415 2-[6-(4-Fluoro-3-methy!-phenyl)pyrro!o[3,2-bjpyridin- l -ylj-N-methyl-N^^^-trifluoroethylJacetamide; 7.2

416 2-[3-Chloro-6-(4-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yij-1 -(3-fiuoroazetidin-i -yljethanone; 5.6 Example Compound Name pICso #

417 2-[3-Chloro-6-(2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -

(3-f!uoroazetidin-1 -y!)ethanone; 7.2

418 2-[3~Chtoro-6~(4-chloro~2-thienyi)pyrrolo[3,2~

b]pyridin-1 -yl]-1 -(3-fluoroazeiidin-1 -yl)eihanone; 6.3

419 N-Eihyl-2-[6-(4-fluorophenyl)pyrroio[3,2-b]pyridin-1 - yl]-N-methyl-acetamide; 7.2

420 2-[3-Ch!oro-6-(2-ihienyl)pyrro!o[3,2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide; 6.2

421 2-[3-Chloro-6-(5-ethyl-2-thienyl)pyrrolo[3,2-b]pyridin-

1 -yl]-N,N~dimethy!-acetamide; 6.2

422 1 -(Azetidin-1 -y!)-2-[3-ch!oro-6-(4-chloro-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.7

423 2-[3-Chloro-6-(5-chloro-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.4

424 2-[3-Ch!oro-6-(5-ethyl-2-thieny!)pyrro!o[3,2-b]pyridin- 1 -yl]-1 ~(3~fluoroazetidin~1 -yi)eihanone; 7.5

425 2-[6-[2-Fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yi]-N,N-dimethyl-acetamide; 6.5

426 2-[6-(5-Ch!oro-4-meihy!-2-thieny!)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.1

427 2-[6-(2,5-Dimeihyl-3-thienyi)pyrrolo[3,2-b]pyridin-1 - yl]-N,N-dimeihy!-acetamide; 7.5

428 N,N-Dimeihy!-2-[6-(2,4,5-tnmethyi-3- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 7.0

429 2-[6-(3-Chlorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide; 6.1 Example Compound Name pICso #

430 2-[6-(4-Fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]-N _! N- dimethyl-acetamide; 7.2

431 2-[6~(2-Fluorophenyl)pyrroto[3,2-b]pyridin~1 -yl]~N _! N- dimethyl-acetamide; 6.6

432 2-[6-(2-Fluoro-3-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]-N,N-dimethyl-acetamide; 6.1

433 N,N-Dimethyl-2-(6-phenylpyrrolo[3,2-b]pyridin-1 - yl)acetamide; 7.6

434 N,N-Dimethyl-2-[6-(m-tolyl)pyrroio[3,2-b]pyridin-1 - yljacetamide; 7.0

435 N,N-Dimethyi-2-[6-[3-

(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.3 y!jacetamide;

436 2-[6-[4-Fluoro-3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.1

437 N,N-Dimethyl-2-[6-(2,3,4-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yijacetamide; 6.5

438 N,N-Dimethyl-2-[6-[5-(trifluoromethyl)-2- thienyl]pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.6

439 2-[6-(5-Ch!oro-3-thieny!)pyrrolo[3,2-b]pyridin-1 -y!]- N,IM~dimeihyl-acetamide; 7.3

440 2-[6-(2,5-Dichloro-3-thienyl)pyrrolo[3,2-b]pyridin-1 - yl]-N,N-dimeihy!-acetamide; 6.9

44 i N,N-Dimethyl-2-[6-[6-(trifluoromethyl)-2- pyridyl]pyrrolo[3,2~b]pyridin~1 -yl]aceiamide; 7.0

442 N,N-Dimethyl-2-[6-[2-(trifluoromethyl)-4- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.8 Example Compound Name pICso #

443 N,N-Dimethyl-2-[6-[5-(trifluoromethyl)-3- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.4

444 2~[6~(2,6~Difluoro-3~meihyi-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 6.2

445 2-[6-(2-Fluoro-5-methyl-phenyl)pyrrolo[3,2-b]pyridin- 1 -yl]-N,N-dimethyl-acetamide; 6.4

446 1 -(Azetidin-1 -yl)-2-[6-[3-

(difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.0 yljethanone;

447 2-[6-(2,4-Difluoro-3-methyl-pbenyl)pyrrolo[3,2- b]pyndin-1 -y!]-N,N-dimeihy!-acetamide; 7.7

448 2-[6-(3-Ch!oro-2-f!uoro-pheny!)pyrrolo[3,2-b]pyridin- 1 -yl]-N,N-dimeihyl-acetamide; 7.7

449 2-[6-(3-Ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide; 7.2

450 2-[6-(3-Fluorophenyl)pyrro!o[3,2-b]pyridin-1 -yl]-N _! N- dimethyl-acetamide; 7.4

451 1 -(Azetidin-1 -yl)-2-[6-(2-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yi]ethanone; 7.3

452 1 -(Azetidin-1 -yl)-2-[6-(2,4-difluoro-3-methyl- pheny pyrrolo^^-bjpyridin-l-yljethanone; 7.6

453 1 -(Azetidin-1 -yi)-2-[6-(3-chioro-2-fluoro- pheny!)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.6

■454 1 -(3-F!uoroazetidin-1 -yl)-2-[6-(2-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.6

455 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone; 7.5 Example Compound Name p!C.¾o #

456 1 -(Azetidin-1 -yl)-2-[6-(3-chloro-4-fluoro- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.2

457 1 -(3-Fiuoroazetidin-1 -yl)-2-[6-(2- fluorophenyl)pyrroio[3,2-b]pyridin-1 -yl]eihanone; 7.8

458 2-[6-[3-(Difluoromethyl)phenyl]pyrrolo[3,2-b]pyridin- 1 -yl]-1 -(3-f!uoroazetidin-1 -y!)ethanone; 6.4

459 N-Eihy!-N-methy!-2-[6-(m-io!yl)pyrrolo[3,2-b]pyridin- 1 -yl]aceiamide; 7.4

460 2-[6-(2,4-Difluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-f!uoroazetidin-1 -yl)etbanone; 7.2

461 2-[6-(3,4-Difluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N- ethyl-N-methyl-acetamide; 7.5

462 N-Ethyl-N-methyl-2-[6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.9

463 1 -(Azetidin-1 -yi)-2-[6-(3-chiorophenyi)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.0

464 N-Ethyl-2-[6-[2-fluoro-3-

(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]-N- 7.9 methyl-acetamide;

465 2-[6-(3-Ch!orophenyl)pyrroio[3,2-b]pyridin-1 -yl]-1 -(3- fiuoroazetidin-1 ~yi)ethanone; 7.1

466 2-[6-(3-Chloro-2-fiuoro-phenyi)pyrrolo[3,2-b]pyridin- 1 -yl]-1 -(3-fiuoroazetidin-1 -yi)ethanone; 7.7

467 2-[6-(3-Chloro-4-fiuoro-phenyi)pyrro!o[3,2-b]pyridin- 1 -yl]-1 ~(3~fluoroazetidin~1 -yl)ethanone; 7.2

468 2-[6-(3-Chloro-4-fluoro-phenyl)pyrrolo[3,2-b]pyridin-

1 -yl]-N,N-dimethy!-acetamide; 7.8 Example Compound Name pICso #

469 2-[6-(2,4-Difluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N-ethyl-N-methyl-acetamide; 7.8

470 N~Ethyl-IM-methyl~2-[6-[3~

(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 6.7 y!jacetamide;

471 1 -(Azeiidin-1 -yl)-2-[3-fluoro-6-(2- f!uoropheny!)pyrrolo[3,2-b]pyridin-1 -y!]eihanone; 7.0

472 1 -(Azeiidin-1 -yl)-2-[3-fluoro-6-(2-fluoro-3-methyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]eihanone; 6.7

473 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -y!jeihanone; 7.5

1 -(Azetidin-1 -yi)-2-[6-(3,5-dif!uoropheny!)-3-fluoro- pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.5

475 1 -(Azeiidin-1 -yl)-2-[3-fluoro-6-[3-

(trif!uoromethy!)phenyl]pyrro!o[3,2-b]pyridin-1 - 7.6 yijethanone;

476 1 -(Azeiidin-1 -yl)-2-[3-fluoro-6-[2-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.3 yljethanone;

477 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.3

478 1 -(Azetidin-1 -y!)-2-[6-(3-ch!orophenyi)-3-f!uoro- pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.4

479 1 -(Azeiidin-1 -yi)-2-[6-(3-chioro-2-fluoro-phenyl)-3- fluoro-pyrroio[3,2-b]pyridin-1 -yl]ethanone; 7.6

480 1 -(Azeiidin-1 -yi)-2-[6-(2,4-difluoro-3-methy!-phenyl)- 3-fluoro~pyrroio[3,2-b]pyridin~1 ~yi]eihanone; 7.4

481 1 -(Azetidin-1 -yi)-2-[6-(3-chioro-4-fluoro-phenyl)-3- fluoro-pyrrolo[3,2-b]pyridin-1 -yl]eihanone; 7.6 Example Compound Name pICso #

482 1 ~(3-Fluoroazeiidin-1 -yl)-2-(3-fluoro-6-phenyl- pyrro!o[3,2-b]pyridin-1 ~yl)ethanone; 7.8

483 1 -(3-Fiuoroazetidin-1 ~yl)~2-[3~fluoro-6~(2-fluoro-3~

methyl-phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.2

484 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.9 yljethanone;

485 1 -(3-F!uoroazetidin-1 -yl)-2-[3-fluoro-6-[2-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.4 yljethanone;

486 1 ~(3-Fluoroazeiidin-1 -yl)-2-[3-fluoro-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyndin-1 -yl]ethanone; 7.6

487 2-[6-(3,5-Dif!uoropheny!)-3-fluoro-pyrro!o[3,2- b]pyridin-1 -yl]-1 ~(3-fluoroazeiidin-1 -yl)eihanone; 7.3

488 2-[6-(2,4-Difiuoro-3-methyl-phenyl)-3-fluoro- pyrrolo[3 _! 2-b]pyridin-1 -y!]-1 -(3-f!uoroazetidin-l - 7.8 yl)eihanone;

489 2-[6-(3-Chloropheny!)-3-f!uoro-pyrro!o[3,2-b]pyridin- 1 -yl]-1 ~(3~fluoroazetidin~1 -yl)eihanone; 8.0

490 2-[6-(3-Chloro-2-fluoro-phenyl)-3-fluoro-pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-fiuoroazetidiri-1 -yl)ethanone; 7.7

491 2-[6-(3-Ethylpheny!)-3-f!uoro-pyrro!o[3,2-b]pyridin-1 - yl]-1 ~(3-fluoroazetidin~1 -yl)ethanone; 7.8

492 1 -(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(3- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -y!]eihanone; 7.6

493 2-[3-Fluoro-6-(2-fluorophenyl)pyrro!o[3,2-b]pyridin-1 - yl]-N,N-dimethyl-acetamide; 7.6

494 2-[3-Fluoro-6-(2-fluoro-3-meihyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yi]-N,N-dimethyl-acetamide; 6.5 Example Compound Name pICso #

495 2-(3-Fluoro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-N,N- dimethyl-acetamide; 7.9

496 2-[3~Fluoro~6-(m-iolyl)pyrroio[3,2-b]pyridin~1 -yl]~N _! N~

dimethyl-acetamide; 7.1

497 1 -(Azetidin-1 -yl)-2-(3-fluoro-6-phenyl-pyrrolo[3,2- b]pyridin-1 -yljethanone; 7.5

498 1 -(Azetidin-1 -yl)-2-[6-(3-ethylpheny!)-3-fiuoro- pyrrolo[3,2-bjpyridin-1 -yljethanone; 7.1

499 2-[3-Fluoro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -y!]-N,N-dimethyi-acetamide; 7.6

500 2-[3-Fiuoro-6-[2-fiuoro-3-

(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]- 7.5

N,N-dimethyl-acetamide;

501 2-[3-Fiuoro-6-(2,3,4-trifiuorophenyl)pyrrolo[3 _! 2- b]pyridin-1 -yl]-IM,N-dimethyi-acetamide; 7.4

502 2-[6-(2,4-Difluoro-3-methy!-phenyl)-3-fiuoro- pyrroio^^-bjpyridin-l -ylj-IM.N-dimethyl-acetamide; 7.4

503 2-[6-(3-Chlorophenyl)-3-fluoro-pyrrolo[3,2-b]pyridin-

1 -yl]-N,N-dimethy!-acetamide; 7.8

504 2-[6-(3-Ch!oro-4-f!uoro-pheny!)-3-fiuoro-pyrro!o[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.9

505 2-[6-(3-Ethylphenyl)-3-fluoro-pyrrolo[3,2-b]pyridin-1 - yl]-N,N-dimeihy!-acetamide; 7.7

506 1 -(Azetidin-1 -yl)-2-[3-fluoro-6-(3- fluorophenyl)pyrroio[3,2-b]pyridin~1 -yljethanone; 7.8

507 1 ~(3-Fluoroazetidin-1 -yl)-2-[3-fluoro-6-(2- fluorophenyl)pyrrolo[3,2-b]pyridin-1 -yljethanone; 7.7 Example Compound Name pICso #

508 1 ~(3-Fluoroazeiidin-1 -yl)-2-[3-fluoro-6-[4-fluoro-3-

(irifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 - 6.9 yljethanone;

509 2-[6~(3,5~Difluorophenyl)~3-fluoro~pyrrolo[3 _! 2~

b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.5

510 2-[3-Fluoro-6-(3-fluorophenyi)pyrrolo[3,2-b]pyridin-1 - yl]-N,N-dimeihy!-aceiamide; 7.4

46 2-[3-Ch!oro-6-(4-fluorophenyl)pyrro!o[3,2-b]pyrid!n-1 - yl]-N,N-dimethyl-acetamide; 7.5

512 2-[3-Chioro-6-(2-fluorophenyl)pyrrolo[3 _i 2-b]pyridin-1 - yl]-N,N-dimethyl-acetamide; 6.5

513 2-[3-Chloro-6-(2-f!uoro-3-methyl-pheny!)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.3

514 2-(3-Chloro-6-phenyl-pyrrolo[3,2-b]pyridin-1 -yl)-N,N- dimethyl-acetamide; 6.9

515 2-[3-Chloro-6-(m-tolyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N- dimethyl-acetamide; 7.0

516 2-[3-Chioro-6-[4-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]- 6.7

N,IM~dimeihyl-acetamide;

517 2-[3-Chioro-6-[2-fiuoro-3-

(trifluoromeihy^phenyljpyrrotop^-bjpyridin-l -yl]- 7.0

N,N-dimethyl-acetamide;

518 2-[3-Chloro-6-(2,3,4-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.2

519 2-[3-Ch!oro-6-(2,4-difluoro-3-meihy!- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]- ,N-dimethyl- 7.2 acetamide;

520 2-[3-Chioro-6-(3-chloro-4-fluoro-phenyl)pyrrolo[3,2- b]pyridin-1 -yi]-N,N-dimethyl-acetamide; 7.1 Example Compound Name pICso #

521 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(2- fluorophenyl)pyrro!o[3,2-b]pyrid!n-1 -yl]ethanone; 6.9

5 1 -(Azeiidin~1 -yl)-2~[3~chloro-6~(2-fluoro~3-methyl~

phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.1

523 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[4-fluoro-3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 6.8 yljethanone;

524 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[2-fluoro-3- (t fluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.1 yljethanone;

525 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(2,4-difluoro-3-methyi- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.3

526 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3- chlorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.2

527 1 -(Azetidin-1 -yl)-2-[3-chioro-6-(3-chloro-4-fiuoro- pheny!)pyrroio[3,2-b]pyridin-1 -yl]ethanone; 7.3

528 1 -(Azetidin-1 -yl)-2-[3-chioro-6-(3-ch!oro-2-fiuoro- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.4

529 1 -(Azetidin-1 -yl)-2-[3-chloro-6-[3-

(difluoromethy!)phenyl]pyrroio[3,2-b]pyridin-1 - 7.1 yljethanone;

530 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3- fiuorophenyi)pyrrolo[3,2~b]pyridin-1 ~yl]ethanone; 7.4

531 2-[3-Chloro-6-(3-fiuorophenyl)pyrroio[3 _! 2-b]pyridin-1 - yl]-N,N-dimethy!-acetamide; 7.3

532 1 -(Azetidin-1 -yi)-2-[3-chioro-6-(3 _! 5- difluorophenyl)pyrroio[3,2-b]pyridin~1 -yl]ethanone; 7.3

533 1 -(Azetidin-1 -yl)-2-[3-chloro-6-(3- ethylphenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.3 Example Compound Name pICso #

534 2-[3-Chloro-6-(3-chlorophenyl)pyrrolo[3,2-b]pyridin-

1 -yl]-N,N~dimethy!-acetamide; 7.5

535 2-[3~Chtoro-6~(2-fluorophenyl)pyrrolo[3 _! 2-b]pyridin~1 - yl]-1 -(3-fluoroazetidin-1 -yl)eihanone; 6.7

536 2-[3-Chloro-6-(2-fluoro-3-methyl-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-fluoroazeiidin-1 -y!)eihanone; 7.6

537 2-[3-Ch!oro-6-(3,5-difluorophenyl)pyrro!o[3,2- b]pyridin-1 -yl]-1 -(3-fluoroazetidin-1 -yl)ethanone; 7.9

538 2-[3-Chloro-6-[2-fluoro-3-

(irifluoromethyl)pheny!]pyrrolo[3 _! 2-b]pyridin-1 -y!]-1 - 7.1 (3~fluoroazetidin~1 -yl)eihanone;

539 2-[3-Cbloro-6-(2,4~dif!uoro-3-metbyl- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-1 -(3-fluoroazeiidin- 7.6 1 -yl)eihanone;

540 2-[3-Chloro-6-(3-chloro-4-fluoro-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-fluoroazeiidin-1 -yl)ethanone; 7.6

541 2-[3-Ch!oro-6-(3-ch!oro-2-f!uoro-pheny!)pyrrolo[3,2- b]pyridin-1 -yl]-1 ~(3-fiuoroazetidin-1 -yl ethanone; 7.4

542 2-[3-Chloro-6-(3-ethylphenyi)pyrrolo[3,2-b]pyridin-1 - yl]-1 -(3-fluoroazeiidin-1 -yi)ethanone; 7.5

543 2-[3-Chloro-6-(3-f!uorophenyl)pyrrolo[3 _! 2-b]pyridin-1 - yl]-1 ~(3-fluoroazetidin~1 -yl)ethanone; 7.7

544 2-[3-Chloro-6-(3-chloro-2-fluoro-phenyl)pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.5

545 2-[3-Ch!oro-6-(3-ch!orophenyl)pyrro!o[3,2-b]pyridin- 1 -yl]-1 ~(3~fluoroazetidin~1 -yi)eihanone; 7.9

546 2-[3-Chloro-6-[3-(difluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-fiuoroazetidiri-1 -yl)ethanone; 7.4 Example Compound Name pICso #

547 1 -(Azetidin-1 -yl)-2-[3-fluoro-2-methyl-6-(m- toiyl)pyrro!o[3,2~b]pyridin-1 -yi]ethanone; 6.4

548 1 ~(Azeiidin~1 -yl)-2~[6~(3,4~difluorophenyl)~3-methyl~

pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.1

549 2-[6-(3,4-Difiuorophenyl)-3-methyi-pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.1

550 1 -(3-F!uoroazetidin-1 -yl)-2-[3-methyl-6-(m- iolyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.9

551 2-[6-(3,4-Difluorophenyl)-3-methyl-pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-f!uoroazetidin-1 -yl)ethanone; 7.2

552 1 -(Azetidin-1 -yl)-2-[3-methyl-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.1 yljeihanone;

553 N,N-Dimethyl-2-[3-methyl-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 7.1 yljacetamide;

554 1 -(3-F!uoroazetidin-1 -yl)-2-[3-methyl-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 6.7 yljethanone;

555 2-[6-(3,5-Difluorophenyl)-3-methyl-pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.2

556 1 -(Azetidin-1 -yl)-2-[6-(3,5-dif!uoropheny!)-3-meihy!- pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.4

557 2-[6-(3,5-Difiuorophenyi)-3-methyi-pyrrolo[3,2- b]pyridin-1 -yl]-N-eihyi-N-meihy!-acetamide; 6.9

558 2-[6-(4-Fluorophenyl)-3-methyl-pyrro!o[3,2-b]pyridin- 1 -yl]-N,N-dimethyl-acetamide; 7.1

559 N-Eihyi-2-[6-(4-fiuorophenyi)-3-methyi-pyrrolo[3,2- b]pyridin-1 -yi]-N-methyl-acetamide; 6.8 Example Compound Name pICso #

560 N-Ethyl-2-[6-(2-fluoro-3-methyl-phenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]-N-methyl-acetamide; 6.1

561 1 -(Azeiidin~1 -yl)-2~[6~(2~fluoro-3~meihyi-phenyl)~3- methyl-pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.4

562 2-[6-(2-Fluoro-3-methyl-phenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.3

563 1 -(3-F!uoroazetidin-1 -yl)-2-[6-(2-fluoro-3-methyl- phenyl)-3-meihyl-pyrroio[3,2-b]pyridin-1 -yl]ethanone; 7.4

564 1 -(3,3-Difluoroazeiidin-l -yl)-2-[6-(2-fluoro-3-methyl- phenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.0

565 2-[6-(2-F!uoro-3~methyl-pheny!)-3-metby!- pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 -yl-ethanone; 6.9

566 2-[6-(4-Fluoro-3-methyl-phenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.3

567 2-[3-fVfeihy!-6-[3-(trif!uoromeihy!)phenyl]pyrro!o[3,2- b]pyridin-1 -yl]-1 ~pyrroiidin~1 -yl-ethanone; 6.7

568 N-Ethyl-N-methyl-2-[3-methyl-6-[3- (trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 - 6.3 yljacetamide;

569 1 -(3,3-Difluoroazeiidin-1 -yl)-2-[3-methyl-6-[3-

(trifluoromeihy^phenyljpyrrotop^-bjpyridin-l - 6.4 yljeihanone;

570 1 -(Azetidin-1 -yl)-2-[3-methyl-6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.2

571 N,N-Dimeihy!-2-[3-meihy!-6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 7.3

572 N,N-Dimethyl-2-[3-methyl-6-(m-tolyl)pyrroio[3 _i 2- b]pyridin-1 -yijacetamide; 7.1 Example Compound Name pICso #

573 N,N-Dimethyi-2-[3-methyl-6-(4-methyl-2- ihienyl)pyrro!o[3,2-b]pyridin-1 -yl]acetamide; 6.9

574 1 -(Azetidin-1 -yl)-2~[3~methyl-6~(4~methyl-2~

thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.1

575 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(4-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 7.1

576 N,N-Dimethyl-2-(3-methyl-6-phenyl-pyrrolo[3,2- b]pyridin-1 -yl)acetamide; 7.0

577 N-Ethyl-N-methyl-2-(3-methyl-6-phenyl-pyrrolo[3,2- b]pyridin-1 -yl)acetamide; 6.7

578 1 -(3-Fluoroazeiidin-1 -yl)~2-(3-metbyl-6-phenyl- pyrrolo[3,2-b]pyridin-1 -yl)ethanone; 6.9

579 1 -(3,3-Difluoroazetidin-1 -yl)-2-(3-methyl-6-phenyl- pyrrolo[3 _! 2-b]pyridin-1 -y!)ethanone; 7.2

580 1 -(3-F!uoroazetidin-1 -yl)-2-[6-(4-fluoro-3-methyl- phenyl)~3~methyl-pyrrolo[3,2~b]pyridin-1 ~yi]eihanone; 7.1

581 1 -(Azetidin-1 -yl)-2-[3-methyl-6-(m-tolyl)pyrrolo[3,2- b]pyridin-1 -yijethanone; 7.1

582 1 -(Azetidin-1 -yl)-2-[3-methyl-6-(2,3,4- trifiuorophenyi)pyrrolo[3,2~b]pyridin~1 -yijethanone; 7.4

583 N.N-Dimethyi^-p-methyl-e^.S^- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.9

584 N-Ethyl-N-methyl-2-[3-methyl-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]acetamide; 6.4

585 1 -(Azetidin-1 -yl)-2-[6-[2-fluoro-3- (trifluoromethyl)phenyl]-3-methyl-pyrrolo[3,2- 6.6 b]pyridin~1 -yijethanone; Example Compound Name pICso #

586 2-[6-[2-Fluoro-3-(trifluoromethyl)phenyl]-3-methyl- pyrro!o[3,2-b]pyridin-1 -yl]-IM,N-d!methyl-acetamide; 6.9

587 N~Ethyl-2-[6-[2~fluoro-3~(trifiuoromeihyi)phenyl]-3- methyl-pyrrolo[3,2-b]pyridin-1 -yl]-N-methyl- 6.6 acetamide;

588 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.2

589 1 -(3-F!uoroazetidin-1 -yl)-2-[6-[2-fluoro-3- (trifluoromethyl)phenyl]-3-methyl-pyrrolo[3,2- 6.9 b]pyridin-1 -yijethanone;

590 2-[6-[2-Fluoro-3-(trifluoromethyl)phenyl]-3-methyl- pyrro!o[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 -yl-ethanone; 6.5

591 2-[3-Methyl-6-(2,3,4-trifluorophenyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 -pyrroiidin-1 -yl-ethanone; 6.9

592 1 -(Azetidin-1 -yl)-2-[6-(2-fluorophenyl)-3-methyi- pyrrolo[3,2-b]pyridin-1 -yijethanone; 6.9

593 2-[6-(2-Fluorophenyl)-3-methyl-pyrrolo[3,2-b]pyridin- 1 -yl]-N,N-dimethyl-acetamide; 6.6

594 N-Ethyl-2-[6-(2-fluorophenyl)-3-methyl-pyrrolo[3,2- bJpyridin-1 -ylJ-N-methyl-acetamide; 6.1

595 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-[2-fluoro-3- (trifluoromethyl)phenylJ-3-methyl-pyrrolo[3,2- 6.6 bjpyridin-1 -yijethanone;

596 1 -(3,3-Difluoroazetidin-1 -yl)-2-[3-methyl-6-(2,3,4- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone; 7.3

597 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[6-(2-f!uoropheny!)-3- methyl-pyrrolo[3,2-b]pyridin-1 -yijethanone; 6.5

598 1 ~(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(3,4,5- trifluorophenyl)pyrrolo[3,2-b]pyridin-1 -yijethanone; 7.4 Example Compound Name pICso #

599 2-[3-Chloro-6-(2,5-dimethyl-3-thienyl)pyrrolo[3,2- b]pyndin-1 -y!]-N,N-dimeihy!-acetamide; 7.0

600 2-[3-Chloro-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.1

601 2-[3-Chloro-6-[6-(trifluoromethyl)-2- pyridyl]pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl- 6.9 aceiamide;

602 2-[3-Ch!oro-6-(5-ch!oro-4-methy!-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl- 8.0 acetamide;

603 2-[3-Chloro-6-[5-(irifluoromethyl)-2- thienyl]pyrrolo[3,2-b]pyridin~1 ~yl]~N,N~dimethyl- 7.2 acetamide;

604 2-[6-(Benzothiophen-2-yl)pyrrolo[3,2-b]pyridin-1 -yl]- N,N-dimethyl-acetamide; 6.7

605 2-[3-Fluoro-6-[4-fluoro-3-

(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridin-1 -yl]- 7.2

N,N-dimethyl-acetamide;

606 2-[6-(3-Chloro-2-fluoro-phenyl)-3-f!uoro-pyrrolo[3 _! 2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.2

607 1 ~(3-Fluoroazeiidin-1 -yl)-2-[3-fluoro-6-(m- io!yl)pyrro!o[3,2-b]pyridin-1 -yl]ethanone; 7.4

608 2-[6-(3-Ch!oro-4-f!uoro-pheny!)-3-fluoro-pyrro!o[3,2- b]pyridin-1 -yl]-1 -(3-fluoroazeiidin-1 -yl)ethanone; 7.7

609 1 -(Azetidin-1 -yl)-2-(3-[ ³ H]-6-(4-fluoro-3- meihy!phenyl)-1 H- NT pyrrolo[3,2-b]pyridin-1 -yl)eihanone;

610 2-[2-Deuterio-6-(4-fluoro-3-meihy!- phenyl)pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl- 8.7 aceiamide;

61 1 2-[6-(3,5-Difiuorophenyl)-3-

(irifluoromethyl)pyrro!o[3,2-b]pyridin-1 -y!]-N,N- 8.0 dimethyl-acetamide; Example Compound Name pICso #

612 3-Ch!oro-1 -(3-pyridyimethyi)-6-[3- (trifluoromeihyi)phenyl]pyrroto[3 _! 2-b]pyridine; 7.5

613 1 -(Pyridazin-3~ylmethyl)~6~[3~

(trif!uoromethyi)phenyl]pyrroio[3,2-b]pyridine; 5.6

614 3-Chloro-6-(4-fiuoro-3-methyl-phenyi)-1 -(pyridazin-3- ylmethyl)pyrrolo[3,2-b]pyridine; 7.5

615 3-Chloro-1 -(pyridazin-3-ylmeihy!)-6-[3- (tnfluoromethyl)phenyi]pyrrolo[3,2-b]pyridine; 7.6

616 2-[6-(4-FiuorQ-3-melhyl-phenyi)-3-metbyi- pyrrolo[3 _! 2~b]pyridin-1 ~yi]-1 ~pyrroiidin~1 ~yi-ethanone; 7.5

617 N-Ethyl-2-[6-(4-fluoro-3-meihy!-phenyl)-3-methyl- pyrrolop^-bjpyridin-l -ylj-N-rneihyl-acetamide; 7.3

618 1 -(3,3-Difluoroazetidin-1 -yl)-2-[6-(4-fiuoro-3-methyl- phenyl)~3~methyl-pyrrolo[3,2~b]pyridin-1 ~yi]eihanone; 7.5

619 2-[6-(3,4-Difluorophenyl)-3-metbyl-pyrro!o[3,2- b]pyridin-1 -yl]-1 -pyrrolidin-1 -yl-eihanone; 7.4

620 2-[6-(3,4-Difluorophenyl)-3-methyl-pyrrolo[3,2- b]pyridin-1 -yl]-N-ethyl-N-methyl-acetamide; 7.6

621 1 -(3,3-Difluoroazeiidin-1 -yl)-2-[6-(3,4- difluorophenyl)-3-meihyl-pyrroio[3,2-b]pyridin-1 - 6.2 yljeihanone;

622 2-[6-(2,4-Difluoro-3-methyl-phenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.0

623 2-[6-(3,5-Difluorophenyl)-3-metbyl-pyrro!o[3,2- b]pyridin-1 -yl]-1 -pyrrolidin-1 -yl-eihanone; 7.8

624 2-[6-(2,4-Difluoro-3-methyl-phenyl)-3-methyl- pyrrolo[3,2-b]pyridin-1 -yl]-1 -pyrrolidin-1 -yl-ethanone; 7.1 Example Compound Name pICso #

625 2-[6-(2,4-Difiuoro-3-methyl-phenyi)-3-meihyi- pyrrolo[3,2-b]pyridin-1 -yl]-N-ethyl-N-methyl- 7.0 acetamide;

626 1 -(3,3-Difiuoroazetidin-1 ~yl)~2-[6~(2,4-difluoro~3- meihy!-phenyl)-3-methyl-pyrrolo[3,2-b]pyridin-1 - 6.2 yljethanone;

627 1 -(Azetidin-1 -yl)-2-[6-(2,4-difluoro-3-meihy!-phenyl)- S-methyl-pyrroiop^-bjpyridin-l -yljethanone; 6.8

628 2-[6-(5-Chloro-2-ihienyi)-3-methyl-pyrro!o[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 7.0

629 2-[6-(2,4-Difiuoro-3-methyl-phenyi)-3-meihyi- pyrrolo[3 _! 2~b]pyridin-1 ~yi]-1 ~(3-fluoroazetidiri-1 - 7.4 yi)ethanone;

630 N-Ethyl-N-methyl-2-[3-methyl-6-(5-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]aceiamide; 6.6

631 2-[3-Methyl-6-(5-methyl-2-thienyl)pyrrolo[3,2- b]pyridin-1 -yl]-1 ~pyrroiidin~1 -yi-ethanone; 6.8

632 1 -(3,3-Dif!uoroazetidin-1 -yl)-2-[3-methyl-6-(5-methyl- 2-thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.7

633 1 -(Azetidin-1 -yl)-2-[3-methyl-6-(5-methyl-2- thienyi)pyrro!o[3,2-b]pyridin-1 -yl]ethanone; 7.3

634 1 -(3-Fluoroazetidin-1 -yl)-2-[3-methyl-6-(5-methyl-2- thienyl)pyrrolo[3,2-b]pyridin-1 -yl]ethanone; 6.2

635 2-[6-(3,5-Difiuorophenyi)-3-methyi-pyrrolo[3,2- b]pyridin-1 -yl]-1 -(3-fluoroazetidin-1 -yi)ethanone; 6.5

636 2-[6-(5-Chloro-2-thienyi)-3-methyl-pyrro!o[3,2- b]pyridin-1 -yl]-1 -(3-fluoroazetidin-1 -yl)ethanone; 6.8

637 N,N-Dimethyi-2-[3-methyl-6-(5-methyl-2- thienyi)pyrro!o[3,2-b]pyridin-1 -yl]acetamide; 6.5 Example Compound Name pICso #

638 1 -(3-Fluoroazetidin-1 -yl)-2-[6-(2-fluorophenyl)-3- methyl-pyrrolo[3,2-bjjpyridin~1 -yljethanone; and 6.9

639 2-[6~[5-(Difluoromeihyl)-2~thienyl]pyrroto[3,2- b]pyridin-1 -yl]-N,N-dimethyl-acetamide; 6.7

^* NT means not tested.