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

HRID 1835915Notes

Reaction equation

HRID 1835915 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

HCID 121489984-benzyloxy-1-(2-fluorobenzenesulfonyl)-1H-indole

Product 1

HCID 114718421-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indoleYield 40.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customA 500 mL round-bottomed flask equipped with a magnetic stirrer
  2. customThe flask was sealed with a rubber septum
  3. custompurged with hydrogen gas at atmospheric pressure
  4. customThe catalyst was removed by filtration through celite
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe resulting crude solid was recrystallized from ethyl ether (75 mL)

Sources & evidence

ORD record
ord-429b58367ca94fe283cbe0ff7f0b3859
Source dataset
uspto-grants-2004_08
Patent number
US06774241B2

Reaction notes

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