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