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Thompson AE, Hughes G, Batsanov AS, et al. Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: synthesis of highly substituted bipyridines and pyrazinopyridines. J Org Chem. 2005;70(1):388-90doi: 10.1021/jo0402226.
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. The Journal of organic chemistry, 70(1), 388-90. https://doi.org/10.1021/jo0402226
Thompson, Amy E, et al. "Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: synthesis of highly substituted bipyridines and pyrazinopyridines." The Journal of organic chemistry vol. 70,1 (2005): 388-90. doi: https://doi.org/10.1021/jo0402226
Thompson AE, Hughes G, Batsanov AS, Bryce MR, Parry PR, Tarbit B. Palladium-catalyzed cross-coupling reactions of pyridylboronic acids with heteroaryl halides bearing a primary amine group: synthesis of highly substituted bipyridines and pyrazinopyridines. J Org Chem. 2005 Jan 07;70(1):388-90. doi: 10.1021/jo0402226. PMID: 15624958.
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J Org Chem. 2005 Jan 07;70(1):388-90. doi: 10.1021/jo0402226.

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

The Journal of organic chemistry

Amy E Thompson, Gregory Hughes, Andrei S Batsanov, Martin R Bryce, Paul R Parry, Brian Tarbit

Affiliations

  1. Department of Chemistry, University of Durham, Durham DH1 3LE, England.

PMID: 15624958 DOI: 10.1021/jo0402226

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.

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