Cesium carbonate → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-4-fluoro-3-(2-oxopyrrolidin-1-yl)-benzamide

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Reaction Steps

A mixture of N-[(1S,2S,4R)-1-benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-bromo-4-fluoro-benzamide (126 mg, 0.24 mmol) (D3), caesium carbonate (117 mg, 0.36 mmol), 2-pyrrolidinone (1 ml of 0.36M solution in 1,4-dioxan, 0.36 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1 ml of 0.015M solution in 1,4-dioxan) and tris(dibenzylideneacetone)dipalladium (0) (1 ml of 0.005M solution in 1,4-dioxan, 0.01 mmol of Pd) was refluxed under argon for 40 h. After cooling, the mixture was filtered and evaporated in vacuo. Column chromatography on silica gel (elution with dichloromethane/methanol) gave the title compound (52 mg) as a white solid.

Provenance & Evidence