Water → HCID 21191894, compound

HRID 2292804Notes

Reaction equation

HRID 2292804 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[CH3:24])[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C(Cl)Cl.O>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[CH3:24])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10854831HCID 10854831, compoundHCID 22277759Boron tribromide dichloromethane2×

Product 1

HCID 21191894HCID 21191894, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 483 mg (1.4 mmol) of 1-[(3-chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetamide and 5.6 mL of 1M BBr3 /methylene chloride in 20 mL of methylene chloride was stirred for 5 hours, 2 mL of 1M BBr3 /methylene chloride added and stirred 16 hours. The mixture was poured into water, extracted with ethyl acetate, the ethyl acetate solution washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted using a gradient, 50% EtOAc/hexane→EtOAc, to give 155 mg of starting material, 1-[(3-chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetamide, and 220 mg (48% yield) off 1-[(3-chlorophenyl)methyl]-5-hydroxy-2-methyl-1H-indole-3-acetamide, mp, 173°-177° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe ethyl acetate solution washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluted

Sources & evidence

ORD record
ord-edff2aab4c5843ccae2c14f7f0238363
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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