The present invention provides methods for the efficient preparation of
indole derivatives of the formula ##STR00001## wherein X is methyl or
benzyl; and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently
hydrogen, halogen, cyano, nitro, hydroxy, optionally substituted alkyl,
alkoxy, aralkoxy, carboxy, alkoxycarbonyl, aryl or heteroaryl; or R.sub.1
and R.sub.2 combined together with the carbon atoms to which they are
attached form a fused 6-membered aromatic ring; by reacting indoles of
the formula ##STR00002## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4
have meanings as defined for formula I, with dimethyl carbonate when X is
methyl, or with dibenzyl carbonate when X is benzyl, in the presence of a
catalytic amount of a base at an ambient temperature to afford compounds
of formula I wherein X, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have
meanings as defined herein above. In particular, the present invention
provides methylation and benzylation of the indole nitrogen in nearly
quantitative yields using 1,4-diazabicyclo[2.2.2]octane as the base in a
catalytic amount under mild conditions, wherein the alkylations may be
conducted in the absence or the presence of an ionic liquid, under
microwave irradiation or utilizing conventional heat, or combinations
thereof.