Copper- and palladium-catalyzed amidation reactions for the synthesis of substituted imidazo[4,5-c]pyridines

Robert J. Wilson; Adam J. Rosenberg; Lauren Kaminsky; Daniel A. Clark

doi:10.1021/jo500064j

Copper- and palladium-catalyzed amidation reactions for the synthesis of substituted imidazo[4,5-c]pyridines

Robert J. Wilson, Adam J. Rosenberg, Lauren Kaminsky, Daniel A. Clark

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Imidazo[4,5-c]pyridines were synthesized in three steps utilizing a palladium-catalyzed amidation/cyclization strategy. N-Aryl substrates were synthesized using copper-catalyzed amidation of 3-amino-N-Boc-4-chloropyridine. Complementary protocols for the selective chlorination of imidazo[4,5-c] pyridines at the C2 and C7 positions were also developed.

Original language	English (US)
Pages (from-to)	2203-2212
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	79
Issue number	5
DOIs	https://doi.org/10.1021/jo500064j
State	Published - Mar 7 2014

ASJC Scopus subject areas

Organic Chemistry

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abstract = "Imidazo[4,5-c]pyridines were synthesized in three steps utilizing a palladium-catalyzed amidation/cyclization strategy. N-Aryl substrates were synthesized using copper-catalyzed amidation of 3-amino-N-Boc-4-chloropyridine. Complementary protocols for the selective chlorination of imidazo[4,5-c] pyridines at the C2 and C7 positions were also developed.",

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AU - Wilson, Robert J.

AU - Rosenberg, Adam J.

AU - Kaminsky, Lauren

AU - Clark, Daniel A.

PY - 2014/3/7

Y1 - 2014/3/7

N2 - Imidazo[4,5-c]pyridines were synthesized in three steps utilizing a palladium-catalyzed amidation/cyclization strategy. N-Aryl substrates were synthesized using copper-catalyzed amidation of 3-amino-N-Boc-4-chloropyridine. Complementary protocols for the selective chlorination of imidazo[4,5-c] pyridines at the C2 and C7 positions were also developed.

AB - Imidazo[4,5-c]pyridines were synthesized in three steps utilizing a palladium-catalyzed amidation/cyclization strategy. N-Aryl substrates were synthesized using copper-catalyzed amidation of 3-amino-N-Boc-4-chloropyridine. Complementary protocols for the selective chlorination of imidazo[4,5-c] pyridines at the C2 and C7 positions were also developed.

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Copper- and palladium-catalyzed amidation reactions for the synthesis of substituted imidazo[4,5-c]pyridines

Abstract

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