2,6-Difluorobenzenesulfonyl chloride → 2,6-difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-ylester

Participants

Reaction Steps

By a method similar to Example 45, using 3-(1-methyl-pyridin-4-yl)-5-hydroxy-1H-indole (1.50 g, 6.5 mmol) in dimethylformamide (40 mL), sodium hydride (0.29 g of a 60% dispersion in oil, 7.2 mmol), 2,6-difluorobenzenesulfonyl chloride (1.52 g, 7.2 mmol) provided 1.35 g (51%) of 2,6-difluorobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-ylester as an off-white solid: mp 235-238° C.; MS(ES+): m/e 407.0 (M+1); 1H NMR (400 MHz, dmso-d6): 11.04 (br s, 1H), 7.92-7.82 (m, 1H), 7.42-7.33 (m, 2H), 7.29 (d, 1H, J=8.8 Hz), 7.15 (d, 1H, J=2.0 Hz), 7.06 (d, 1H, J=2.0 Hz), 6.79 (dd, 1H, J=8.8, 1.8 Hz), 2.78 (br d, 2H, J=11.2 Hz), 2.56-2.46 (m, 1H), 2.16 (s, 3H), 1.93 (br t, 2H, J=11.8 Hz), 1.74-1.64 (m, 2H), 1.60-1.46 (m, 2H).

Provenance & Evidence