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Efficient Access to Azaindoles and Indoles

Mark McLaughlin,* Michael Palucki and Ian W. Davies

*Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, Email:

M. McLaughlin, M. Palucki, I. W. Davies, Org. Lett., 2006, 8, 3307-3310.

DOI: 10.1021/ol061232r


An effective reductive alkylation of electron-deficient o-chloroarylamines was developed. The derived N-alkylated o-chloroarylamines were elaborated to N-alkylazaindoles and N-alkylindoles via a novel one-pot process comprising copper-free Sonogashira alkynylation and a base-mediated indolization reaction.

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Key Words

reductive amination, aryl amines, Sonogashira coupling, indoles, azaindoles

ID: J54-Y2006-2100