Rearrangement of 4-amino-3-halo-pyridines by nucleophilic aromatic substitution.

J Org Chem

Drug Discovery Program, Ontario Institute for Cancer Research, 101 College Street, MaRS Centre, South Tower, Toronto, ON M5G 0A3, Canada.

Published: June 2013

The reaction of 3-halo-4-aminopyridines with acyl chlorides and triethylamine is described. The pyridin-4-yl α-substituted acetamide products were obtained in moderate to high yields. The presented rearrangement reaction, in which the presumed N-acylated intermediate reacts intramolecularly via nucleophilic aromatic substitution, results in a formal two-carbon insertion.

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http://dx.doi.org/10.1021/jo4003773DOI Listing

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