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

Participants

Role	Name	HCID	Charge
Reactant	Chlorine	HCID 24526	—
Reactant	Boron tribromide	HCID 25134	—
Reactant	1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-methoxyl-1H-indole	HCID 10546013	—
Product	1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-hydroxy-1H-indole	HCID 10617069	29.2%

Reaction Steps

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 /CH2 Cl2. 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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05733923
Source dataset	uspto-grants-1998_03
ORD ID	ord-4a94e879ce5b4777a46e8ccc576b08e1
Source note	uspto-grants-1998_03