Sodium hydride → 2,6-Difluorobenzenesulfonic acid 7-methyl-1-phenethyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester hydrochloride

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Reaction Steps

By a method similar to Example 56, using 7-methyl-3-(1-methylpiperdin-4-yl)-1-phenethyl-1H-indol-5-ol (0.55 mmol, 0.190 g) in THF (1.4 mL), sodium hydride (0.65 mmol, 0.026 g, 60% dispersion in mineral oil), and 2,6-diflurobenzenesulfonyl chloride (0.60 mmol, 0.128 g) afforded 0.136 g (44%) of the title compound: MS (ion spray): m/z=511 (M+1); 1H NMR (DMSOd6): 7.97-7.87 (m, 1H), 7.45-7.38 (m, 2H), 7.29-7.17 (m, 2H), 7.13 (d, 2H), 6.63 (d, J=1.10 Hz, 1H), 4.53 (t, J=7.50 Hz, 2H), 3.47-3.39 (m, 2H), 3.11-2.95 (m, 4H), 2.87-2.69 (m, 4H), 2.60 (s, 3H), 1.94-1.71 (mm, 4H); Calculated for C28H28F2N2O3S-1.9 H2O: C, 61.73; H, 5.88; N, 5.14. Found: C, 61.43; H, 5.51; N, 4.93.

Provenance & Evidence