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 Et 3 N.

No abstract