Sodium hydride → [[2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester

HRID 581153Notes

Reaction equation

HRID 581153 reaction equation
[CH:1]1([C:4]2[N:5]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]3[C:11]([CH:12]=2)=[C:10]([OH:13])[CH:9]=[CH:8][CH:7]=3)[CH2:3][CH2:2]1.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].[H-].[Na+]>CN(C=O)C>[CH3:26][O:25][C:23](=[O:24])[CH2:22][O:13][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:12]=[C:4]([CH:1]1[CH2:2][CH2:3]1)[N:5]2[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 104918052-cyclopropyl-4-hydroxy-1-(phenylmethyl)-1H-indole

Product 1

HCID 10568807[[2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Cyclopropyl-4-hydroxy-1-(phenylmethyl)-1H-indole (316 mg, 1.2 mmol) was alkylated by treating with 0.11 mL (1.2 mmol) of methyl bromoacetate and 48 mg (1.2 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 253 mg (63% yield) of [[2-cyclopropyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester.

Workup

  1. customThe product was purified by chromatography over silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-0aa52e10d7ea431aa7d81657ed85d5f8
Source dataset
uspto-grants-1999_07
Patent number
US05919810

Reaction notes

Loading…