Water → 1-(4-difluoromethoxybenzenesulfonyl)-5-iodo-1H-indole

Participants

Reaction Conditions

Reaction Steps

5-Iodo-1H-indole (2.0 g, 8.23 mmol) was dissolved in dimethylformamide (DMF) (10 ml) and cooled to 0° C. Sodium hydride (494 mg, 12.34 mmol) was added in small portions. The reaction mixture was stirred for 1 hour at 0° C. 4-(Difluoro-methoxy)-benzenesulfonyl chloride (2.196 g, 9.05 mmol) was dissolved in DMF (5 ml), and added slowly to the reaction mixture. Stirring was continued for 45 minutes. Cold water (150 ml) was added to the reaction mixture. The reaction mixture was extracted twice with ethyl acetate (100 ml). The organic layer was dried over magnesium sulphate, filtered, and the solvent evaporated under reduced pressure to give a crystalline solid (3.0 g, 81%). ESI-MS [m/z]: 449.95 [M+H]+. 1H-NMR (500 MHz, d6-DMSO): δ=8.05 (d, 2H), 8.0 (s, 1H), 7.85 (d, 1H), 7.8 (d, 1H), 7.65 (d, 1H), 7.4 (t, J=70 Hz, 1H), 7.35 (d, 2H), 6.8 ppm (d, 1H).

Provenance & Evidence