Water → HCID 86686915, 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 3-(trifluoromethyl)benzenesulfonyl chloride (76 μL, 0.474 mmol). After stirring for ˜10 minutes at 0° C., the light yellow reaction mixture was allowed to warm to room temperature and then was stirred for overnight at room temperature. Water (˜25 mL) was added and the mixture was extracted with methylene chloride (2×30 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. Silica gel chromatography (25-33% ethyl acetate in hexanes) afforded {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (104 mg, 84%). MS cald. for C26H26F4NO4S [(M+H)+]: 524, obsd. 524.1.

Provenance & Evidence