2,4-Dichlorobenzoyl chloride → HCID 86686920, compound

Participants

Reaction Steps

To a light brown 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-dichlorobenzoyl chloride (110 mg, 0.53 mmol) in dichloromethane (10 mL) was added N,N-diisopropylethylamine (183 μL, 1.05 mmol) at room temperature under a nitrogen atmosphere. The resulting light brown solution was stirred for 15 hours. The reaction mixture was diluted with water and brine and the resulting mixture was extracted into ethyl acetate (2×50 mL). The combined organic extracts were washed with brine solution, dried over MgSO4, filtered, and concentrated to give the crude product. Flash chromatography (40 g ISCO column, eluting with 0-60% ethyl acetate/hexanes) provided {4-[1-(2,4-dichloro-benzoyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (111 mg, 65%) as a white solid. MS cald. for C26H25Cl2FNO3 [(M+H)−] 488, obsd. 488.0.

Provenance & Evidence