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

HRID 3371Notes

Reaction equation

HRID 3371 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[CH2:19][CH2:20][CH3:21].B(Br)(Br)Br.ClCl>>[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[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 3

HCID 24526ChlorineHCID 25134Boron tribromideHCID 106419401-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-propyl-1H-indole

Product 1

HCID 108547301-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-propyl-1H-indoleYield 71.1%

Procedure

By the method used in Example 1, Part D, 1.16 g (3.27 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-4-methoxy-2-propyl-1H-indole was O-demethylated by treating it with 13 mL of 1M BBr3 /CH2 Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 794 mg (71% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-propyl-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-a277cd76b49147da9acb93045c400b7a
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Reaction notes

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