1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-methyl-1H-indole → 1-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-methyl-1H-indole

HRID 581119Notes

Reaction equation

HRID 581119 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([O:17]C)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH3:19]>B(Br)(Br)Br.C(Cl)Cl>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH3:19]

Participants

3

Reactant 1

HCID 107349911-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-methyl-1H-indole

Product 1

HCID 108051531-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-methyl-1H-indoleYield 55%

Reagents, catalysts & solvents 1

HCID 22277759Boron tribromide dichloromethaneSolvent

Procedure

By the method used in Example 1, Part D, 1.6 g (4.9 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-methyl-1H-indole was O-demethylated by treating it with 20 mL of 1M BBr3 /CH2Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 841 mg (55% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-methyl-1H-indole.

Workup

  1. customThe crude product was chromatographed on silica gel
  2. washeluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-46f381dad35342a580586188d028f88a
Source dataset
uspto-grants-1999_07
Patent number
US05919810

Reaction notes

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