Green N-Methylation of Electron Deficient Pyrroles with Dimethylcarbonate

Abstract Image

The N-methylation of electron-deficient pyrroles was affected using dimethyl carbonate in the presence of DMF and catalytic DABCO. This alkylation methodology has proven useful for the alkylation of a variety of pyrroles in 72−98% yields and is considered to be greenchemistry relative to the more common use of methyl halides or dimethyl sulfate.

Eli Lilly and Company, Chemical Product Research and Development Division, Indianapolis, Indiana 46285, U.S.A
Org. Process Res. Dev., 2009, 13 (6), pp 1199–1201
DOI: 10.1021/op900256t
Publication Date (Web): October 26, 2009
Herein, the N-methylation of compound 1 along with a number of commercially available pyrrole derivatives using DMC, DMF and catalytic 1,4-diazabicyclo[2.2.2]octane (DABCO) are described.
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