Sodium Hydroxide → HCID 10202580, compound

Participants

Reaction Steps

By a method similar to Example 31, using 0.2N sodium hydroxide (2.4 mmol, 12.2 mL), 2,6-difluorobenzenesulfonyl chloride (2.9 mmol, 0.625 g), 6-fluoro-3-(1-methylpiperidin-4-yl)-1H-indole-5-ol (2.4 mmol, 0.608 g) in THF (7.7 mL). The crude isolated product was subjected to normal phase silica gel radial chromatography, 4 mm plate eluting with 9:1 methylene chloride:2M ammonia in methanol at 10 mL/minute. Fractions containing product combined, concentrated in vacuo to a white solid. The title compound was crystallized from methylene chloride to afford 0.282 g (27%) of the title compound: mp=202° C.; Mass spectrum (ion spray): m/z=425 (M+1); 1H NMR (DMSOd6): 11.10 (s, 1H), 7.91 (m, 1H), 7.40 (m, 2H), 7.26-7.16 (m, 3H), 2.78 (m, 2H), 2.52 (m, 1H), 2.20 (s, 3H), 1.96 (m, 2H), 1.69 (m, 2H), 1.51 (m, 2H); Calculated for C20H19F3N2O3S: C, 56.12; H, 4.57; N, 6.54. Found: C, 56.13; H, 4.56; N, 6.48.

Provenance & Evidence