N-alkylation of indole and pyrroles in dimethyl sulphoxide

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Abstract
The potassium salts of indole, pyrrole, and 2,5-dimethylpyrrole were converted into N-alkyl derivatives in high yield in dimethyl sulphoxide by use of iodomethane, iodoethane, 1-iodopropane, and benzyl bromide. Dehydrohalogenation occurred when 2-iodo- and 2-bromo-2-methylpropane were used; when 2-iodopropane was employed alkylation and dehydrohalogenation were observed.