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
Org. Lett., 2006, 8 (15), pp 3307–3310
DOI: 10.1021/ol061232r
Publication Date (Web): June 22, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mark_mclaughlin@merck.com

Abstract

Abstract Image

An expedient, catalytic method for the synthesis of diverse azaindoles and indoles, starting from readily available and inexpensive starting materials, is described. Conditions were developed for effective reductive alkylation of electron-deficient o-chloroarylamines, substrates previously viewed as poor partners in this reaction. 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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History

  • Published In Issue July 20, 2006
  • Received May 19, 2006

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