4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole → 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole

HRID 3359

Reaction equation

HRID 3359 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:23])[N:7]2[CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.B(Br)(Br)Br.C(Cl)Cl>CCOC(C)=O.CCCCCC>[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:23])[N:7]2[CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 106380394-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indoleHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 104935294-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indoleYield 71%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

By the method used in Example 1, Part D, 1.17 g (3.9 mmol) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole was O-demethylated by treating it with 15.6 mL of 1M BBr3 /CH2Cl2 to give a material that was chromatographed on silica gel (eluted with 20% EtOAc/hexane then 50% EtOAc/hexane) to give 796 mg (71% yield) of 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.

Workup

  1. customto give a material that
  2. customwas chromatographed on silica gel (
  3. washeluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-ac45098226724296a2030ef33a83f824
Source dataset
uspto-grants-1998_03
Patent number
US05733923

Linked notes

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