Sodium hydride → (1-Benzyl-2-ethyl-1H-indol-4-yloxy)-acetic acid methyl ester

HRID 1795190Notes

Reaction equation

HRID 1795190 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>CN(C)C=O.O>[CH3:27][O:26][C:24](=[O:25])[CH2:23][O:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:3]([CH2:1][CH3:2])[N:4]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 98164161-Benzyl-2-ethyl-1H-indol-4-OL

Product 1

HCID 10687371(1-Benzyl-2-ethyl-1H-indol-4-yloxy)-acetic acid methyl esterYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole (1.56 g, 6.2 mmol) is treated with 248 mg (6.2 mmol) of 60% NaH/mineral oil in dimethylformamide and the mixture stirred for 0.67 hours. 0.6 mL(6.2 mmol) of methyl bromoacetate is added and the mixture stirred for 17 hours. The reaction mixture is diluted with water and then extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried, and concentrated at reduced pressure. The product is purified by chromatography over silica gel eluting with 20% EtOAc/hexane, to give 1.37 g (69% yield) of [[2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester, 89-92° C.

Workup

  1. stirringthe mixture stirred for 17 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution is washed with brine
  4. customdried
  5. concentrationconcentrated at reduced pressure
  6. customThe product is purified by chromatography over silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-999faf11e35c4519a3372b62a30622cd
Source dataset
uspto-grants-2006_04
Patent number
US07026348B2

Reaction notes

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