Ethyl bromoacetate → HCID 86646549, compound

HRID 1038764Notes

Reaction equation

HRID 1038764 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)=[N:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C=O)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][N:15]1[C:16]2[C:12](=[C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=3)[CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1)[CH3:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 14071978HCID 14071978, compound

Product 1

HCID 86646549HCID 86646549, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5-Nitropyridin-2-yloxy)-1H-indole (3.34 g, 13.1 mmol) was dissolved in DMF (20 mL). To the solution were added 60% sodium hydride (0.523 g, 13.1 mmol) and ethyl bromoacetate (1.45 mL, 13.1 mmol) under cooling with ice, and the resulting solution was stirred for 1 hour. Ice water (150 mL) was added to the solution, and the mixture was extracted with ethyl acetate (150 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. Thus obtained residue was purified by silica gel column chromatography (AcOEt:n-hexane=1:3), and then the obtained solid was recrystallized from ethyl acetate and n-hexane to yield 1.84 g of the title compound as a yellow powder.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe mixture was extracted with ethyl acetate (150 mL)
  3. washAfter the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThus obtained residue was purified by silica gel column chromatography (AcOEt:n-hexane=1:3)
  7. customthe obtained solid was recrystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-ac2c186f751e4ae08ce78a849ebc9742
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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