2,5-Dichlorobenzenesulfonyl chloride → HCID 86686908, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 102 mg, 0.237 mmol) and N,N-diisopropylethylamine (124 μL, 0.711 mmol) in methylene chloride (6.0 mL) was added 2,5-dichlorobenzenesulfonyl chloride (116 mg, 0.474 mmol). After stirring for ˜15 minutes at 0° C., the light yellow reaction mixture was allowed to warm to room temperature and then was stirred overnight at room temperature under nitrogen. During this time, some solvent evaporated. Methylene chloride (˜10 mL) and water (˜25 mL) were added. The resulting mixture was extracted with methylene chloride (2×25 mL). The combined extracts were washed with brine solution then concentrated to give the crude product which was purified by elution from a silica gel plug (20% ethyl acetate in hexanes) to give {4-[1-(2,5-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (52 mg, 42%) as an off-white solid. MS cald. for C25H25Cl2FNO4S [(M+H)+]: 524, obsd. 524.0.

Provenance & Evidence