Sodium Hydroxide → 2,6-Difluorobenzenesulfonic acid 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1h-indol-5-yl ester

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Reaction Steps

By a method similar to Example 31, using a solution of 2,6-difluorobenzenesulfonyl chloride (380 mg, 1.79 mmol) in THF (5 mL) was added to a mixture of 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-hydroxy-1H-indole (340 mg, 1.49 mmol) in 0.2 N sodium hydroxide (8.2 mL, 1.64 mmol) and THF (5 mL) gave 170 mg (28%) of homogeneous product as a tan solid. The product was crystallized from ethyl acetate to give 96 mg (16%) of the title compound as a yellow powder: mp 183° C. dec; MS(m/e): 405 (M+1), 403 (M−1); Calculated for C20H18F2N2O3S: C, 59.40; H, 4.49; N, 6.93. Found: C, 59.22; H, 4.24; N, 6.65.

Provenance & Evidence