HCID 10500247, compound → 1-([1,1'-biphenyl]-2-ylmethyl)-5-hydroxy-2-methyl-1H-indole-3-acetamide

HRID 1069608Notes

Reaction equation

HRID 1069608 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]C)=[CH:14][CH:15]=2)[C:10]([CH2:19][C:20]([NH2:22])=[O:21])=[C:9]1[CH3:23].B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([CH2:19][C:20]([NH2:22])=[O:21])=[C:9]1[CH3:23]

Participants

4

Reactant 2

HCID 10500247HCID 10500247, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 106905301-([1,1'-biphenyl]-2-ylmethyl)-5-hydroxy-2-methyl-1H-indole-3-acetamideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 369 mg (0.96 mmol) of 1-([1,1′-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetamide and 4 mL of 1M BBr3/methylene chloride in 20 mL of methylene chloride was stirred for 6 hours. The mixture was concentrated at reduced pressure, the residue dissolved in ethyl acetate, washed with water, brine and dried (MgSO4). After concentrating at reduced pressure, the residue was chromatographed on silica gel and eluted with EtOAc to give 295 mg (85% yield) of 1-([1,1′-biphenyl]-2-ylmethyl)-5-hydroxy-2-methyl-1H-indole-3-acetamide.

Workup

  1. concentrationThe mixture was concentrated at reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentrating at reduced pressure
  6. customthe residue was chromatographed on silica gel
  7. washeluted with EtOAc

Sources & evidence

ORD record
ord-e1ac4825e7ed4b81bae3653e42e09147
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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