Water → HCID 86695027, compound

Participants

Reaction Steps

A stirred solution of [6-fluoro-3-methyl-4-(4,4,5,5-tetra methyl-[1,3,2]-dioxaborolan-2-yl)-naphthalen-2-yl]-acetic acid methyl ester (0.200 g, 0.56 mmol) in dimethoxyethane (5 mL) was purged with argon for 5 minutes at room temperature. Tetrakis(triphenylphosphine)palladium(0) (0.065 g, 0.056 mmol), 4-bromo-N-(2-hydroxyethyl)-benzenesulfonamide (0.157 g, 0.56 mmol) and 2.0 M aqueous sodium carbonate (0.8 mL, 1.6 mmol) were added simultaneously to the reaction mixture under argon. The reaction was refluxed for 2 hours and then cooled to room temperature. Water was added and the mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product, which was finally purified using flash chromatography to afford {6-fluoro-4-[4-(2-hydroxyethylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (0.070 g, 29%) as a solid. MS calcd. for C22H21FNO5S [(M−H)−] 430, obsd. 430.3.

Provenance & Evidence