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

HRID 566643Notes

Reaction equation

HRID 566643 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C.O>[CH3:26][O:25][C:23](=[O:24])[CH2:22][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Product 1

HCID 10804819(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid methyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole (530 mg, 2.2 mmol) was added to 88 mg (2.2 mmol) of 60% NaH/mineral oil in 20 mL of DMF and the mixture stirred for 0.67 hours. Then, 0.21 mL (2.2 mmol) of methyl bromoacetate was added and stirring maintained for 17 hours. The mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4), and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 597 mg (88% yield) of [[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester, 140-143° C.

Workup

  1. stirringstirring
  2. temperaturemaintained for 17 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-7d756693fcfa4faf979e8a269f22c7d4
Source dataset
uspto-grants-2001_01
Patent number
US06175021B1

Reaction notes

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