Diisopropylethylamine → HCID 86686907, compound

Participants

Reaction Steps

To a 0° C. solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester (which may be prepared as described above; 110 mg, 0.35 mmol) and 2,4-dichlorobenzenesulfonyl chloride (171 mg, 0.7 mmol) in THF (6.0 mL) was added N,N-diisopropylethylamine (183 μL, 1.05 mmol). The resulting light yellow solution was allowed to warm to room temperature during 2 hours and then it was stirred for 15 hours at room temperature under nitrogen. The reaction mixture was diluted with water and brine solution and the organic compound was extracted into ethyl acetate (2×50 mL). The combined extracts were washed with brine solution and dried over MgSO4. Filtration and concentration gave the crude product which was purified by flash chromatography (40 g ISCO column, eluting with 0-60% ethyl acetate in hexanes) to give {4-[1-(2,4-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (119 mg, 65%) as an off-white solid. MS cald. for C20H25FNO4S [(M+H)+] 524, obsd. 523.8.

Provenance & Evidence