Cesium carbonate → 1-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A suspension of 93.7 mg (0.655 mmol) 4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester (synthesis described in J. Leroy et al. Tetrahedron 58, p. 6713, 2002) and 640 mg (1.96 mmol) cesium carbonate in 1.3 ml DMF is heated to 50° C. under stirring. 167 mg (0.655 mmol) 2-bromo-1-(4-tert-butyl-phenyl)ethanone is added and the reaction mixture is stirred for 18 hours at 50° C. The reaction mixture is filtered with suction and the filtrate is evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 1-[2-(4-tert-butyl-phenyl)-2-oxo-ethyl]-4-fluoro-1H-pyrrole-2-carboxylic acid methyl ester as brown amorphous solid; HPLC/MS 3.26 min (B), [M+H] 318.

Provenance & Evidence