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Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: Synthesis of highly substituted bipyridines and pyrazinopyridines

Thompson, A.E.; Hughes, G.; Batsanov, A.S.; Bryce, M.R.; Parry, P.R.; Tarbit, B.

Authors

A.E. Thompson

G. Hughes

A.S. Batsanov

P.R. Parry

B. Tarbit



Abstract

A range of halogenated aromatics and heteroaromatics bearing a primary amine group are shown to be suitable substrates for Suzuki cross-coupling reactions with arylboronic acids and pyridylboronic acids under standard conditions, without the need for protection/deprotection steps. New amino-substituted arylpyridines, bipyridines, and pyrazinopyridines have thereby been obtained. Conditions for the efficient syntheses of 2-methoxy-5-pyridylboronic acid 1 and 2-methoxy-3-pyridylboronic acid 2 in ca. 75 g batches have been defined. A 2-fold reaction of 2-amino-5-bromopyrazine with 2,5-dimethoxy-1,4-benzenediboronic acid affords 1,4-dimethoxy-2,5-bis[2-(5-aminopyrazyl)] benzene 31. The X-ray crystal structures of 1 and 31(.)DMF are reported.

Citation

Thompson, A., Hughes, G., Batsanov, A., Bryce, M., Parry, P., & Tarbit, B. (2005). Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: Synthesis of highly substituted bipyridines and pyrazinopyridines. Journal of Organic Chemistry, 70(1), 388-390

Journal Article Type Article
Publication Date 2005-01
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 70
Issue 1
Pages 388-390