Synthesis and reactions of 4,6-dimethoxyindole,an unusual indole system

A synthesis of 4,6-dimethoxyindole is described. Formylation or oxalylation reactions gave substitution at position 7 rather than the usual 3-substitution characteristic of other indoles. A synthesis of N,N-dimethyl-4,6-dimethoxytryptamine is presented along with NMR data for 3 and 7-substituted compounds in this series.