Condensed Heteroaromatic Ring Systems. XII.1) Synthesis of Indole Derivatives from Ethyl 2-Bromocarbanilates

Abstract

The palladium-catalyzed reaction of ethyl 2-bromocarbanilate with trimethylsilylacetylene yielded ethyl 2-(trimethylsilylethynyl)carbanilate, which was treated with sodium ethoxide to give indole. The carbanilates having a methyl or a bromo substituent were similarly transformed to corresponding indole derivatives. Furthermore, pyrrolo[3, 2-b]- and pyrrolo[3, 2-c]pyridines were synthesized by this method. © 1987, The Pharmaceutical Society of Japan. All rights reserved.