Diisopropylethylamine → HCID 86686918, compound

Participants

Reaction Conditions

Reaction Steps

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; 560 mg, 1.78 mmol) and (2-nitrophenyl)methanesulfonyl chloride (837 mg, 3.55 mmol) in THF (30 mL) was cooled to 0° C. under nitrogen and then N,N-diisopropylethylamine (930 μL, 5.34 mmol) was added. The resulting light brown solution was stirred for 2 hours at 0° C. temperature and then allowed to warm to room temperature and stirred for 36 hours. The reaction mixture was diluted with water and brine and the organic compound was extracted into ethyl acetate (2×100 mL). The combined organic layers were washed with brine and dried over MgSO4, filtered, and concentrated. The crude product was purified using flash chromatography (120 g ISCO column eluting with 0-60% ethyl acetate/hexanes) to give {6-fluoro-3-methyl-4-[1-(2-nitro-phenylmethanesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (645 mg, 71%) as a light yellow solid. 1H NMR (400 MHz, Chloroform-d) δ 8.07-8.1 (m, 1H), 7.85 (br. s, 1H), 7.55 (dd, J=8.8, 6.3 Hz, 1H), 7.67-7.72 (m, 2H), 7.56-7.64 (m, 2H), 7.16-7.24 (m, 1H), 4.83 (s, 2H), 3.89 (d, J=10.0 Hz, 2H), 3.82 (br. s, 2H), 3.72 (s, 3H), 3.43-3.63 (m, 1H), 2.90 (t, J=11.5 Hz, 2H), 2.32-2.71 (m, 5H), 1.77 (d, J=13.8 Hz, 2H). MS cald. for C26H27FN2O6S [(M+H)+] 514, obsd. 515.2.

Provenance & Evidence