4-benzyloxy-1-(2-fluorobenzenesulfonyl)-1H-indole → 1-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indole
Reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])(=[O:20])=[O:19])C1C=CC=CC=1>[Pd].C1COCC1>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[S:18]([N:13]1[C:14]2[C:10](=[C:9]([OH:8])[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1)(=[O:19])=[O:20]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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.