Heumann Indole Flow Chemistry Process

J Org Chem. 2019 Sep 6;84(17):10929-10937. doi: 10.1021/acs.joc.9b01516. Epub 2019 Aug 8.

Abstract

Continuous flow chemistry has improved efficiency in the Heumann indole process. 3-Substituted indoles were prepared by three flow steps performed in succession in better overall yield and shorter reaction times relative to their batch counterparts. Novel 3-alkyl and 3-methoxyindoles were synthesized from their corresponding amino ketone and ester precursors by flow sequences featuring base-free alkylation with methyl bromoacetate in DMF, saponification, and cyclization with acetic anhydride and Et3N.

Publication types

  • Research Support, Non-U.S. Gov't