Phenylmethanesulfonyl chloride → HCID 86686910, 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 α-toluenesulfonyl chloride (90.4 mg, 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 stirred for 4 hours at room temperature under nitrogen. During this time, some solvent had evaporated. The reaction mixture was diluted with water (˜25 mL) and extracted with methylene chloride (3×25 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography (eluting with 33% ethyl acetate/hexanes) to give [6-fluoro-3-methyl-4-(1-phenylmethanesulfonyl-piperidin-4-yl)-naphthalen-2-yl]-acetic acid methyl ester (88 mg, 79%). MS cald. for C26H29FNO4S [(M+H)+]: 470, obsd. 470.2.

Provenance & Evidence