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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2256220Generated: October 26, 2026

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

https://huagongshe.com/reaction/2256220

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
ReactantMethyl bromoacetateHCID 60984—
Reactant1-([1,1'-biphenyl]-2-ylmethyl)-4-hydroxy-2-methyl-1H-indoleHCID 10805153—
SolventDimethylformamideHCID 6228—
Product[[1-([1,1'-biphenyl]-2-ylmethyl)-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl esterHCID 1179449377.3%

Reaction Steps

1-([1,1'-Biphenyl]-2-ylmethyl)-4-hydroxy-2-methyl-1H-indole (767 mg, 2.45 mmol) was alkylated by treating with 0.23 mL (2.45 mmol) of methyl bromoacetate and 98 mg (2.45 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 730 mg(77% yield) of [[1-([1,1'-biphenyl]-2-ylmethyl)-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester, 99°-101° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05654326
Source datasetuspto-grants-1997_08
ORD IDord-4786e6c8a50f4513a3c547bd0a516049
Source noteuspto-grants-1997_08