An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine

S Caron, SS Massett, DE Bogle…

Index: Caron, Stephane; Massett, Steve S.; Bogle, David E.; Castaldi, Michael J.; Braish, Tamim F. Organic Process Research and Development, 2001 , vol. 5, # 3 p. 254 - 256

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Citation Number: 47

Abstract

The synthesis of 2-phenyl-3-aminopyridine, a key intermediate in the preparation of 2- phenyl-3-aminopiperidine, from 2-chloro-3-aminopyridine is described using an imine as a protecting group for an aminopyridine. The in situ protection of 2-chloro-3-aminopyridine with benzaldehyde followed by Suzuki coupling with phenylboronic acid and subsequent acid hydrolysis provided the titled compound in a single, high-yielding step from ...