Cesium carbonate → [6-Fluoro-4-(4-methanesulfonyl-phenylamino)-naphthalen-2-yl]-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (6-fluoro-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (115 mg, 0.31 mmol) and 4-methanesulfonyl-phenylamine (59 mg, 0.35 mmol) in N,N-dimethylformamide (3 mL), was added (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (39 mg, 0.063 mmol), tris(dibenzylideneacetone)dipalladium(0) (14 mg, 0.016 mmol), and cesium carbonate (102 mg, 0.31 mmol). After being heated under microwave conditions (160° C., 15 minutes), the resulting mixture was diluted with water (10 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was washed with brine, then dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (gradient elution with 0-50% ethyl acetate in hexanes) to afford [6-fluoro-4-(4-methanesulfonyl-phenylamino)-naphthalen-2-yl]-acetic acid methyl ester (84.0 mg, 69% yield) as a yellow solid.

Provenance & Evidence