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; Daniel A Clark

doi:10.1021/ol300359s

Synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines by palladium catalyzed amidation of 2-chloro-3-amino-heterocycles

Org Lett. 2012 Apr 6;14(7):1764-7. doi: 10.1021/ol300359s. Epub 2012 Mar 13.

Authors

Adam J Rosenberg¹, Jinbo Zhao, Daniel A Clark

Affiliation

¹ Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA.

PMID: 22414201
DOI: 10.1021/ol300359s

Abstract

A facile synthesis of imidazo[4,5-b]pyridines and -pyrazines is described using a Pd-catalyzed amide coupling reaction. This reaction provides quick access to products with substitution at N1 and C2. 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.