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

Takao Sakamoto, Yoshinori Kondo, Shigeki Iwashita, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

51 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1823-1828
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume35
Issue number5
DOIs
Publication statusPublished - 1987

Keywords

  • ethyl 2-(trimethylsilylethynyl)carbanilate
  • ethyl 2-halocarbanilate
  • ethyl 2-halopyridinecarbamate
  • ethyl o-(trimethylsilylethynyl)pyridinecarbamate
  • indole
  • palladium-catalyzed reaction
  • pyrrolopyridine
  • trimethylsilylacetylene

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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