Efficient access to azaindoles and indoles.
[Structure: see text] 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.
McLaughlin
Mark
M
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. mark_mclaughlin@merck.com
Palucki
Michael
M
Davies
Ian W
IW
D000478:Alkylation; D001372:Aza Compounds / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure
D001372:Aza Compounds; D007211:Indoles