The regiospecific bromination of various substituted 3-methylindoles a
t either C(2) or the C(3) alkyl moiety was accomplished via an electro
philic or free radical bromination process to provide intermediates fo
r indole alkaloid total synthesis. The regiospecificity of the bromina
tion could be controlled by variation of both the substituent and the
N(1) protecting group on the indole ring.