2-Chlorobenzenesulfonyl chloride → HCID 86686905, compound

Participants

Reaction Steps

To a solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester (which may be prepared as described above; 108 mg, 0.34 mmol) and 2-chlorobenzenesulfonyl chloride (145 mg, 0.69 mmol) in THF (6 mL) was added excess N,N-diisopropylethylamine (179 μL, 1.0 mmol) at 0° C. under a nitrogen atmosphere. The resulting light brown solution was allowed to warm slowly to room temperature over 2 hours, was and then stirred for 15 hours at room temperature under a nitrogen atmosphere. The reaction mixture was diluted with water and brine solution and the organic compound was extracted with ethyl acetate (2×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration and concentration gave a crude brown oil which was purified by flash chromatography (40 g ISCO column, eluting with 0-60% ethyl acetate/hexanes) to give {4-[1-(2-chloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (110 mg, 65%) as an off-white solid. MS cald. for C25H26ClFNO4S [(M+H)+] 490, obsd. 490.0.

Provenance & Evidence