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