Can be dimetallated using the n-BuLi/KO-t-Bu system. Reaction with electrophiles (methyl iodide, benzophenone, t-butyl isocyanate) then occurs preferentially at the more reactive methyl position: J. Chem. Soc., Perkin 1, 179 (1990). An alternative approach to functionalization of the 2-methyl group involves low-temperature N-lithiation followed by reaction with dimethyl carbonate to give the 1-methoxycarbonyl derivative. NBS ɑ-bromination then allows nucleophilic substitution to give a variety of 2-substituted indoles: Synthesis, 743 (1992). Undergoes a mild, selective C-3 reductive alkylation in the presence of Triethyl-silane, A10320, and TFA; e.g. with benzaldehyde, the 3-benzyl derivative is formed in 88% yield: Tetrahedron Lett., 34, 1529 (1993).
