NaH (26 mg, 1.07 mmol) was added in several batches to a solution of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carbonitrile (200 mg, 0.76 mmol) in DMF (2 mL) at 0-5° C., and the mixture was maintained for 1 hour at room temperature. Benzenesulfonyl chloride (222 mg, 1.24 mmol) was then added, and the resulting solution was maintained at room temperature for an additional 4 hours. The mixture was filtered, and the filter cake was washed with ethanol (2×10 mL) and diethylether (2×10 mL) to afford 250 mg (86%) of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-indole-5-carbonitrile as a white solid. 1H NMR (DMSO) δ 8.41 (s, 1H), 8.14 (d, 2H), 8.07 (d, 2H), 7.78 (d, 1H), 7.71 (d, 2H), 7.61 (t, 1H), 6.35 (s, 1H), 3.79 (2H), 3.34 (s, 2H), 2.80-2.87 (m, 5H).
