HCID 11792628, compound → HCID 10497528, compound

HRID 1069621Notes

Reaction equation

HRID 1069621 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=3)[C:11]([CH2:20][C:21]([NH2:23])=[O:22])=[C:10]2[CH2:24][CH3:25])[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[C:11]([CH2:20][C:21]([NH2:23])=[O:22])=[C:10]2[CH2:24][CH3:25])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11792628HCID 11792628, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 10497528HCID 10497528, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 226 mg (0.63 mmol) of 1-[(3-chlorophenyl)methyl]-2-ethyl-5-methoxy-1H-indole-3-acetamide and 2.5 mL of 1M BBr3/methylene chloride in 15 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 174 mg (81% yield) of 1-[(3-chlorophenyl)methyl]-2-ethyl-5-hydroxy-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 and dried(MgSO4)
  4. concentrationAfter concentrating at reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. washeluted with EtOAc

Sources & evidence

ORD record
ord-747431b8af6c4e288ed80782baca2040
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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