Title:
METHOD OF SYNTHESIZING PHARMACEUTICAL INTERMEDIATE PHENANTHRENE COMPOUND IN THE PRESENCE OF DIISOPROPYLAMINE
Document Type and Number:
WIPO Patent Application WO/2016/141827
Kind Code:
A1
Abstract:
The present invention relates to a method of synthesizing a phenanthrene compound, represented by formula (I), in the presence of a diisopropylamine. The method comprises: in an inert atmosphere, and in the presence of a catalyst, an organic ligand, and a diisopropylamine, reacting in a solvent a compound represented by formula (II) and a compound represented by formula (III) to obtain a compound represented by formula (I), wherein R1 and R2 are independently an H, a C1-C6 alkyl, a C1-C6 alkyloxy or a halogen; R3 is a C6-C10 aryl or a C5-C8 heteroaryl; the C6-C10 aryl or the C5-C8 heteroaryl is optionally substituted with 1-3 substituent groups; and the substituent groups are a C1-C6 alkyl or a halogen. The method obtains a favorable result by selecting a suitable catalyst, an organic ligand, a base, and a solvent, and has a wide prospect for an industrial application.
Inventors:
ZHAI XUEYAN (CN)
Application Number:
PCT/CN2016/075404
Publication Date:
September 15, 2016
Filing Date:
March 03, 2016
Export Citation:
Assignee:
JIN YINGHUA (CN)
International Classes:
C07B37/10; C07C2/42; C07C17/275; C07C15/30; C07C25/22; C07D213/127; C07D213/16
Foreign References:
| CN104692986A | 2015-06-10 | |||
| CN102827077A | 2012-12-19 |
Other References:
KIM K.H. ET AL.: "2,3-Dichloro-5,6-dicyano-para-benzoquinone (DDQ)/Methanesulfonic Acid (MsOH)-Mediated Intramolecular Arene-Alkene Oxidative Coupling Adv.", SYNTH. CATAL., vol. 356, no. 4, 20 February 2014 (2014-02-20), ISSN: 1615-4169
YAO, QINGWEI ET AL.: "Ligand-Free Heck Reaction: Pd (OAc) 2 as an Active Catalyst Revisited", J. ORG. CHEM., vol. 68, no. 19, 16 August 2003 (2003-08-16), XP001170659, ISSN: 0022-3263
SHIMIZU M. ET AL.: "Palladium-catalyzed double cross-coupling reaction of 1,2-bis (pinacolatoboryl) alkenes and-arenes with 2,2'-dibromobiaryls: annulative approach to functionalized polycyclic aromatic hydrocarbons", TETRAHEDRON, vol. 69, no. 41, 12 August 2011 (2011-08-12), pages 8014 - 8026, XP028288356, ISSN: 0040-4020
YAO, QINGWEI ET AL.: "Ligand-Free Heck Reaction: Pd (OAc) 2 as an Active Catalyst Revisited", J. ORG. CHEM., vol. 68, no. 19, 16 August 2003 (2003-08-16), XP001170659, ISSN: 0022-3263
SHIMIZU M. ET AL.: "Palladium-catalyzed double cross-coupling reaction of 1,2-bis (pinacolatoboryl) alkenes and-arenes with 2,2'-dibromobiaryls: annulative approach to functionalized polycyclic aromatic hydrocarbons", TETRAHEDRON, vol. 69, no. 41, 12 August 2011 (2011-08-12), pages 8014 - 8026, XP028288356, ISSN: 0040-4020
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