4-benzyloxy-1-(2-fluorobenzenesulfonyl)-1H-indole → 1-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indole

Participants

Reaction Steps

A 500 mL round-bottomed flask equipped with a magnetic stirrer was charged with a solution of 4-benzyloxy-1-(2-fluorobenzenesulfonyl)-1H-indole (21.48 g, 0.056 mol) in 200 mL freshly distilled THF, followed by 5% palladium on carbon (0.100 g, 0.8 mol %). The flask was sealed with a rubber septum and purged with hydrogen gas at atmospheric pressure. The solution was stirred at ambient temperature for 6 hours. The catalyst was removed by filtration through celite, and the filtrate concentrated in vacuo. The resulting crude solid was recrystallized from ethyl ether (75 mL) to give 1-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indole as a white solid (6.55 g, 40%). MS: (M−H)−=290.1.

Provenance & Evidence