Diisopropylethylamine → HCID 86686911, 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-methoxybenzenesulfonyl chloride (98 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 was stirred for 4 hours at room temperature under nitrogen. During this time, some solvent had evaporated. Additional methylene chloride was added. 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 and concentrated. Silica gel chromatography (20-33% ethyl acetate/hexanes) afforded {6-fluoro-4-[1-(2-methoxy-benzenesulfonyl)-piperidin-4-yl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (64 mg, 55%). MS cald. for C26H29FNO5S [(M+H)+]: 486, obsd. 486.2.

Provenance & Evidence