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

HRID 566680Notes

Reaction equation

HRID 566680 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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[CH:19]1[CH2:21][CH2:20]1.B(Br)(Br)Br.C(Cl)Cl>>[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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[CH:19]1[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 105460131-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-methoxyl-1H-indoleHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 106170691-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-hydroxy-1H-indoleYield 29.2%

Procedure

By the method used in Example 1, Part D, 1.25 g (3.7 mmol) of 1-([1,1′-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-methoxyl-1H-indole was O-demethylated by treating it with 15 mL of 1M BBr3/CH2Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 367 mg (29% yield) of 1-([1,1′-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-hydroxy-1H-indole as an oil.

Workup

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

Sources & evidence

ORD record
ord-43b427facf5f418b99020f1bde5effc1
Source dataset
uspto-grants-2001_01
Patent number
US06175021B1

Reaction notes

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