An Efficient Synthesis of 1-Methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine and Its N⁶-Substituted Analogues

An efficient synthesis of 1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine hydrochloride was achieved using simple sodium borohydride reduction of 6-benzyl-1-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium bromide as the key step followed by its debenzylation with hydrogen over palladium on carbon on a multigram scale. Similarly, a series of N⁶-substituted 1-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium halides were synthesized and reduced with sodium borohydride, showing this method to be applicable for the synthesis of different N6-substituted 1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridines.

Nechayev M. A.; Gorobets N. Y.; Kovalenko S. M.; Tolmachev A. A.
Synthesis 2013, 45 (07), 919-924
DOI: 10.1055/s-0032-1318346