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.

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. E., Hughes, G., Batsanov, A. S., Bryce, M. R., Parry, P. R., & 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
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 70
• Issue: 1
• Pages: 388-390
• Public URL: https://durham-repository.worktribe.com/output/1568264