Title:
METHOD FOR RAPIDLY METHYLATING HETEROAROMATIC RING ARYL AND METHOD FOR PRODUCING PET TRACER
Document Type and Number:
WIPO Patent Application WO/2010/074272
Kind Code:
A1
Abstract:
Provided is a method whereby a heteroaromatic ring aryl can be very rapidly methylated at a high yield. In an N-alkyl-2-pyrrolidinone, a heteroaromatic ring aryltrialkylstannan is cross-coupled with methyl iodide in the presence of a palladium complex, a phosphine ligand, a cuprous halide, a carbonic acid salt and/or an alkali metal fluoride to thereby rapidly methylate the heteroaromatic ring aryl. (Formula shows a case wherein the heteroaromatic ring aryl is a pyridyl group.)
Inventors:
SUZUKI MASAAKI (JP)
DOI HISASHI (JP)
KOYAMA HIROKO (JP)
DOI HISASHI (JP)
KOYAMA HIROKO (JP)
Application Number:
PCT/JP2009/071694
Publication Date:
July 01, 2010
Filing Date:
December 25, 2009
Export Citation:
Assignee:
UNIV GIFU (JP)
RIKEN (JP)
SUZUKI MASAAKI (JP)
DOI HISASHI (JP)
KOYAMA HIROKO (JP)
RIKEN (JP)
SUZUKI MASAAKI (JP)
DOI HISASHI (JP)
KOYAMA HIROKO (JP)
International Classes:
C07D213/127; A61K51/00; C07D217/02; C07D231/12; C07D237/08; C07D239/26; C07D307/36; C07D333/08; C07B61/00
Domestic Patent References:
| WO2007046258A1 | 2007-04-26 | |||
| WO2007046258A1 | 2007-04-26 | |||
| WO2008023780A1 | 2008-02-28 |
Other References:
IIDA, Y. ET AL.: "Evaluation of 5-11C-methyl-A- 85380 as an imaging agent for PET investigations of brain nicotinic acetylcholine receptors", THE JOURNAL OF NUCLEAR MEDICINE, vol. 45, no. 5, 2004, pages 878 - 884, XP008148848
BENNACEF, I. ET AL.: "Functionalization through Lithiation of (S)-N-(1-Phenylpropyl)-2- phenylquinoline-4-carboxamide. Application to the Labeling with Carbon-11 of NK-3 Receptor Antagonist SB 222200", JOURNAL OF ORGANIC CHEMISTRY, vol. 72, no. 6, 2007, pages 2161 - 2165, XP002509397
BAO, Z. ET AL.: "Exploration of the Stille Coupling Reaction for the Synthesis of Functional Polymers", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 117, no. 50, 1995, pages 12426 - 12435, XP002430212
FARINA, V. ET AL.: "Large rate accelerations in the stille reaction with tri-2-furylphosphine and triphenylarsine as palladium ligands: mechanistic and synthetic implications", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 113, no. 25, 1991, pages 9585 - 9595, XP002923480
MEE, S.P. ET AL.: "Stille coupling made easier - the synergic effect of copper(I) salts and the fluoride ion", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 43, no. 9, 2004, pages 1132 - 1136, XP003012119
See also references of EP 2383258A4
M. SUZUKI, H. DOI, M. BJORKMAN, Y. ANDERSON, B. LANGSTROM, Y. WATANABE, R. NOYORI, CHEM. EUR. J., vol. 3, no. 12, 1997, pages 2039 - 2042
T. HOSOYA, K. SUMI, H. DOI, M. SUZUKI, ORG. BIOMOL. CHEM., vol. 4, 2006
J. TARKIAINEN, J. VERCOUILLIE, P. EMOND, J. SANDELL, J. HILTUNEN, Y. FRANGIN, D. GUILLOTEAU, C. HALLDIN, J. LABELLED COMPD. RADIOPHARM., vol. 44, 2001, pages 1013 - 1023
J. PRABHAKARAN, V. J. MAIO, N. R. SIMPSON, R. L. V. HEERTUM, J. J. MANN, J. S. D.KUMAR, J. LABELLED, COMPDS. RADIOPHARM., vol. 48, 2005
M. SUZUKI, R. NOYORI, B. LANGSTROM, Y. WATANABE, BULL. CHEM. SOC. JPN., vol. 73, 2000
M. SUZUKI, H. DOI, T. HOSOYA, B. LANGSTROM, Y. WATANABE, TRENDS ANAL. CHEM., vol. 23, 2004
R. NOYORI, ANGEW. CHEM., INT. ED. ENGL., vol. 41, 2002
T. HOSOYA, M. WAKAO, Y. KONDO, H. DOI, M. SUZUKI: "Rapid methylation of terminal acetylenes by the Stille coupling of methyl iodide with alkynyltributylstannanes: a general protocol potentially useful for the synthesis of short-lived 11CH3-labeled PET tracers with 1-propynyl group", ORG. BIOMOL. CHEM., vol. 2, 2004, pages 24 - 27
J. SANDELL, M. YU, P. EMOND, L. GARREAU, S. CHALON, K. NAGREN, D. GUILLOTEAU, C. HALLDIN, BIOORG. MED. CHEM. LETT., vol. 12, 2002, pages 3611 - 3613
IIDA, M., OGAWA, M., UEDA, A., TOMINAGA, H., KAWASHIMA, Y., MAGATA, S., NISHIYAMA, H., TSUKADA, T., MUKAI, H. SAJI, J. NUCL. MED., vol. 45, 2004, pages 878 - 884
Y. HUANG, R. NARENDRAN, F. BISCHOFF, N. GUO, Z. ZHU, S.-A BAE, A. S. LESAGE, M. LARUELLE, J. MED. CHEM., vol. 48, 2005, pages 5096 - 5099
1. BENNACEF, C. PERRIO, M.C.LASNE, L. BARRE, J. ORG. CHEM., vol. 72, 2007, pages 2161 - 2165
K. MENZEL, G. C. FU, J. AM. CHEM. SOC., vol. 125, 2003, pages 3718 - 3719
H. TANG, K. MENZEL, G. C. FU, ANGEW,INT. ED. ENGL., vol. 42, 2003, pages 5079 - 5082
J. BALDWIN ET AL., ANGEW. CHEM. INT. ED., vol. 43, 2004, pages 1132 - 1136
BENNACEF, I. ET AL.: "Functionalization through Lithiation of (S)-N-(1-Phenylpropyl)-2- phenylquinoline-4-carboxamide. Application to the Labeling with Carbon-11 of NK-3 Receptor Antagonist SB 222200", JOURNAL OF ORGANIC CHEMISTRY, vol. 72, no. 6, 2007, pages 2161 - 2165, XP002509397
BAO, Z. ET AL.: "Exploration of the Stille Coupling Reaction for the Synthesis of Functional Polymers", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 117, no. 50, 1995, pages 12426 - 12435, XP002430212
FARINA, V. ET AL.: "Large rate accelerations in the stille reaction with tri-2-furylphosphine and triphenylarsine as palladium ligands: mechanistic and synthetic implications", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 113, no. 25, 1991, pages 9585 - 9595, XP002923480
MEE, S.P. ET AL.: "Stille coupling made easier - the synergic effect of copper(I) salts and the fluoride ion", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 43, no. 9, 2004, pages 1132 - 1136, XP003012119
See also references of EP 2383258A4
M. SUZUKI, H. DOI, M. BJORKMAN, Y. ANDERSON, B. LANGSTROM, Y. WATANABE, R. NOYORI, CHEM. EUR. J., vol. 3, no. 12, 1997, pages 2039 - 2042
T. HOSOYA, K. SUMI, H. DOI, M. SUZUKI, ORG. BIOMOL. CHEM., vol. 4, 2006
J. TARKIAINEN, J. VERCOUILLIE, P. EMOND, J. SANDELL, J. HILTUNEN, Y. FRANGIN, D. GUILLOTEAU, C. HALLDIN, J. LABELLED COMPD. RADIOPHARM., vol. 44, 2001, pages 1013 - 1023
J. PRABHAKARAN, V. J. MAIO, N. R. SIMPSON, R. L. V. HEERTUM, J. J. MANN, J. S. D.KUMAR, J. LABELLED, COMPDS. RADIOPHARM., vol. 48, 2005
M. SUZUKI, R. NOYORI, B. LANGSTROM, Y. WATANABE, BULL. CHEM. SOC. JPN., vol. 73, 2000
M. SUZUKI, H. DOI, T. HOSOYA, B. LANGSTROM, Y. WATANABE, TRENDS ANAL. CHEM., vol. 23, 2004
R. NOYORI, ANGEW. CHEM., INT. ED. ENGL., vol. 41, 2002
T. HOSOYA, M. WAKAO, Y. KONDO, H. DOI, M. SUZUKI: "Rapid methylation of terminal acetylenes by the Stille coupling of methyl iodide with alkynyltributylstannanes: a general protocol potentially useful for the synthesis of short-lived 11CH3-labeled PET tracers with 1-propynyl group", ORG. BIOMOL. CHEM., vol. 2, 2004, pages 24 - 27
J. SANDELL, M. YU, P. EMOND, L. GARREAU, S. CHALON, K. NAGREN, D. GUILLOTEAU, C. HALLDIN, BIOORG. MED. CHEM. LETT., vol. 12, 2002, pages 3611 - 3613
IIDA, M., OGAWA, M., UEDA, A., TOMINAGA, H., KAWASHIMA, Y., MAGATA, S., NISHIYAMA, H., TSUKADA, T., MUKAI, H. SAJI, J. NUCL. MED., vol. 45, 2004, pages 878 - 884
Y. HUANG, R. NARENDRAN, F. BISCHOFF, N. GUO, Z. ZHU, S.-A BAE, A. S. LESAGE, M. LARUELLE, J. MED. CHEM., vol. 48, 2005, pages 5096 - 5099
1. BENNACEF, C. PERRIO, M.C.LASNE, L. BARRE, J. ORG. CHEM., vol. 72, 2007, pages 2161 - 2165
K. MENZEL, G. C. FU, J. AM. CHEM. SOC., vol. 125, 2003, pages 3718 - 3719
H. TANG, K. MENZEL, G. C. FU, ANGEW,INT. ED. ENGL., vol. 42, 2003, pages 5079 - 5082
J. BALDWIN ET AL., ANGEW. CHEM. INT. ED., vol. 43, 2004, pages 1132 - 1136
Attorney, Agent or Firm:
AOYAMA, Yo (JP)
Aoyama Sun (JP)
Aoyama Sun (JP)
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