Water → 6-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide

HRID 2292780Notes

Reaction equation

HRID 2292780 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:20][C:21]([NH2:23])=[O:22])=[C:8]([CH3:19])[N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:20][C:21]([NH2:23])=[O:22])=[C:8]([CH3:19])[N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 108286266-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide

Product 1

HCID 105657326-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamideYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.53 g (5 mmol) of 6-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide was added 20 mL (20 mmol) of 1M BBr3 in methylene chloride and the mixture stirred for 3 hours. Water was added and the mixture extracted with EtOAc. The EtOAc solution was washed with a NaCl solution, dried (MgSO4), and concentrated at reduced pressure. The residue was chromatographed on silica and the product eluted with 5% MeOH/methylene chloride to give 658 mg (45% yield) of 6-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 174°-179° C.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washThe EtOAc solution was washed with a NaCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was chromatographed on silica
  6. washthe product eluted with 5% MeOH/methylene chloride

Sources & evidence

ORD record
ord-0292fda54aab409882880e4daf89ee19
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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