3-(Trifluoromethyl)phenyl isocyanate → HCID 86686927, compound

Participants

Reaction Steps

To a solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester (which may be prepared as described above; 94 mg, 0.298 mmol) in methylene chloride (6.0 mL) was added trifluoro-m-tolyl isocyanate (82 μL, 0.596 mmol) at room temperature under nitrogen. The resulting light brown solution was stirred at room temperature for 40 minutes. The reaction mixture was diluted with water (˜25 mL) and the resulting mixture was extracted with methylene chloride (3×25 mL). The combined organic layers were washed with saturated aqueous NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to a yellow-orange film. Silica gel chromatography (20-25% ethyl acetate in hexanes) provided {6-fluoro-3-methyl-4-[1-(3-trifluoromethyl-phenylcarbamoyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (97 mg, 65%) as a colorless film. MS cald. for C27H27F4N2O3 [(M+H)+]: 503, obsd. 503.2.

Provenance & Evidence