1-([1,1'-biphenyl]-3-ylmethyl)-4-methoxy-2-methyl-1H-indole → HCID 10495408, compound

HRID 1741136Notes

Reaction equation

HRID 1741136 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]=[C:3]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([O:17]C)[CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:19])[CH:2]=1.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]=[C:3]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:19])[CH:2]=1

Participants

3

Reactant 2

HCID 107586031-([1,1'-biphenyl]-3-ylmethyl)-4-methoxy-2-methyl-1H-indoleHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 10495408HCID 10495408, compoundYield 87%

Procedure

A solution of 125 mg (3.8 mmol) of 1-((1,1'-biphenyl)-3-ylmethyl)-2-methyl-4-methoxy-1H-indole is O-demethylated by treating it with 15 mL of 1M BBr3 /CH2Cl2. The reaction mixture is stirred at room temperature for 5 hours and concentrated at reduced pressure. The crude product is chromatographed on silica gel and is eluted with 20% EtOAc/hexane to give 1030 mg (87% yield) of 1-((1,1'-biphenyl)-3-ylmethyl)-2-methyl-4-hydroxy-1H-indole.

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThe crude product is chromatographed on silica gel
  3. washis eluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-b2d5739fa97c4b2880077c9881043d66
Source dataset
uspto-grants-1999_10
Patent number
US05972988

Reaction notes

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