Synlett 2004(13): 2394-2396  
DOI: 10.1055/s-2004-832836
LETTER
© Georg Thieme Verlag Stuttgart · New York

Cesium Carbonate Promoted N-Alkylation of Indoles

David M. Fink*
Aventis Pharmaceuticals, Department of Medicinal Chemistry, Route 202-206, Bridgewater, NJ 08807, USA
e-Mail: david.fink@aventis.com.;
Further Information

Publication History

Received 24 April 2004
Publication Date:
24 September 2004 (online)

Abstract

The N-alkylation of indoles with alkyl halides and epoxides, using cesium carbonate as the base in DMPU, is reported.

9

Using n-butyllithium as the base in THF as in ref. 2 resulted in a slow but clean conversion to product (24% conversion at reflux for 18 h). However, if DMPU was used as solvent, then the product was formed at r.t. over 48 h.

12

The products exhibited satisfactory 1H NMR spectra.