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Paper | Special issue | Vol 70, No. 1, 2006, pp.201-205
Published online, 14th July, 2006
DOI: 10.3987/COM-06-S(W)4
Direct Conversion of Substituted Pyrrole-2-carboxylic Acid Methyl Esters to Their 2-Carbonitrile Analogues

Xun Li,* Michael Reuman, and Ronald K. Russell

*US Resarch & Early Development, Johnson & Johnson Pharmaceutical Research & Development, L. L. C., 1000 Route 202, Rartan, New Jersey 08869, U.S.A.

Abstract

Small to large quantity (1-136 g) of substituted pyrrole-2-carbonitrles were reproducibly prepared from their corresponding 2-carboxylic acid methyl esters in one step with 53-61% yield and high chemical purity (>97%), with using dimethylaluminum amide [(CH3)2AlNH2] that was freshly generated by treating anhydrous ammonia (NH3) and trimethylaluminum [(CH3)3Al] at -40 °C in chlorobenzene, a modified Weinreb’s method.