Novel metal-free coupling reaction of azoles with 2- or 3-haloindoles

ORGN 641

Martin Poirier, mpoirier@lav.boehringer-ingelheim.com1, Sébastien R. Goudreau, sebastien.goudreau@umontreal.ca2, Jason Poulin3, Jolaine Savoie3, and Pierre L. Beaulieu, pbeaulieu@lav.boehringer-ingelheim.com4. (1) Departement of Chemistry, Boehringer Ingelheim (Canada) Ltd, 2100 Cunard, Laval, QC H7S2G5, Canada, (2) Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada, (3) Université de Sherbrooke, Sherbrooke, QC, Canada, (4) Department of Chemistry, Boehringer Ingelheim Canada Ltd, 2100 Cunard Street, Laval, QC H7S2G5, Canada
A novel reaction involving a metal-free, direct coupling of azoles and 2-bromoindoles was discovered. This reaction is acid catalyzed and does not appear to proceed through an SNAr process. Successful cross-coupling is dependent on the pKa of the azole heterocycle. More synthetically accessible 3-haloindoles reacted under similar conditions and also produced the desired 2-substituted indoles. This reaction provides convenient access to novel and biologically useful heterocyclic systems under environmentally friendly conditions. The scope and limitations of this new reaction will be presented and possible mechanisms will be discussed.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006