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

TAKAO SAKAMOTO; YOSHINORI KONDO; SHIGEKI IWASHITA; HIROSHI YAMANAKA

doi:10.1248/cpb.35.1823

TAKAO SAKAMOTO, YOSHINORI KONDO, SHIGEKI IWASHITA, HIROSHI YAMANAKA

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Keywords: palladium-catalyzed reaction, trimethylsilylacetylene, ethyl 2-halocarbanilate, ethyl 2-halopyridinecarbamate, ethyl 2- (trimethylsilylethynyl) carbanilate, ethyl ο- (trimethylsilylethynyl) pyridinecarbamate, indole, pyrrolopyridine

JOURNAL FREE ACCESS

1987 Volume 35 Issue 5 Pages 1823-1828

DOI https://doi.org/10.1248/cpb.35.1823

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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.

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