Preparation of 2-substituted pyrroles and indoles by regioselective alkylation and deprotection of 1-(2-trimethylsilyllethoxymethyl)pyrrole and 1-(2-trimethylsulylethoxymethyl) indole

Article abstract of DOI:10.1016/S0040-4020(01)87342-7

After N-alkylation of pyrrole and indole with 2-trimethylsilylethoxymethyl chloride the products of the reaction could be regioselectively deprotonated with n-butyllithium at the 2-position.Reaction of the resulting anions with acid chlorides, lactones, silyl chlorides or aldehydes gave addition products, some of which were deprotected to the parent pyrrole or indole using anhydrous tetra-n-butylammonium fluoride.