Ammonium formate → 1-(Phenylsulfonyl)-1H-indol-5-ol

HRID 2423125Notes

Reaction equation

HRID 2423125 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[CH:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>C1COCC1.CO.[Pd]>[C:21]1([S:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=3)[CH:12]=[CH:13]2)(=[O:19])=[O:20])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 118246245-(Phenylmethoxy)-1-phenylsulfonylindole2×

Product 1

HCID 99705131-(Phenylsulfonyl)-1H-indol-5-olYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Pd/C 10 wt. % (0.10 g, 0.094 mmol) was added to a solution of 5-(benzyloxy)-1-(phenylsulfonyl)-1H-indole (Intermediate 7, 6.00 g, 16.5 mmol) and ammonium formate (15.6 g, 248 mmol) in THF/MeOH 1:1 (300 mL). The reaction mixture was stirred overnight at room temperature and filtered through a short plug of silica gel. The filtrate was evaporated and dissolved in DCM and filtered through a plug of silica gel eluating with 2.5% MeOH in DCM. The purest fractions (monitored by TLC) were evaporated to give the title compound (4.2 g) as a white powder. MS m/z 273 [M+H]+.

Workup

  1. filtrationfiltered through a short plug of silica gel
  2. customThe filtrate was evaporated
  3. dissolutiondissolved in DCM
  4. filtrationfiltered through a plug of silica gel eluating with 2.5% MeOH in DCM
  5. customThe purest fractions (monitored by TLC) were evaporated

Sources & evidence

ORD record
ord-a6a0f526ab254b6aa00827ed58def583
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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