Sodium hydride → [[1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-1H-indol-4-yl]oxy]acetic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Sodium hydride	HCID 24758	—
Reactant	Methyl bromoacetate	HCID 60984	—
Reactant	2-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indole	HCID 10616205	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[[1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-1H-indol-4-yl]oxy]acetic acid methyl ester	HCID 10524971	59%

Reaction Steps

1-([1,1'-Biphenyl]-2-ylmethyl)-2-ethyl-4-hydroxy-1H-indole (911 mg, 2.8 mmol) was alkylated by treating with 0.26 mL (2.8 mmol) of methyl bromoacetate and 111 mg (2.8 mmol) of 60% NaH/mineral oil in DMF as described in Example 1, Part E. The product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane, to give 655 mg (59% yield) of [[1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-1H-indol-4-yl]oxy]acetic acid methyl ester.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05733923
Source dataset	uspto-grants-1998_03
ORD ID	ord-a877d6e90efd4757a0744545d7206df9
Source note	uspto-grants-1998_03