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Synthesis of Imidazo[4,5-b]pyridines and Imidazo[4,5-b]pyrazines by Palladium Catalyzed Amidation of 2-Chloro-3-amino-heterocycles

Adam J. Rosenberg, Jinbo Zhao and Daniel A. Clark*

*Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, United States, Email:

A. J. Rosenberg, J. Zhao, D. A. Clark, Org. Lett., 2012, 14, 1761-1767.

DOI: 10.1021/ol300359s

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A Pd-catalyzed amide coupling reaction enables a facile synthesis of imidazo[4,5-b]pyridines and -pyrazines. This reaction provides quick access to various substituted products. A model system relevant to the natural product pentosidine has been demonstrated, as well as the total synthesis of the mutagen 1-Me-5-PhIP.

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Key Words

benzo-fused N-heterocycles

ID: J54-Y2012-0970