Ethyl bromoacetate → HCID 15728950, compound

HRID 1377633Notes

Reaction equation

HRID 1377633 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[NH:14][CH:13]=[CH:12][N:10]3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[CH2:22]([O:21][C:19]([CH2:18][N:14]1[C:9]2[N:10]([N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=2)[CH:12]=[CH:13]1)=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178420057HCID 178420057, compound

Product 1

HCID 15728950HCID 15728950, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 0.4 g of 6-phenyl-1H-imidazo[1,2-b]-pyrazole in 10 ml of dimethylformamide was slowly added dropwise, whilst stirring at room temperature, to 96 mg of a 55% w/w suspension of sodium hydride in mineral oil, which was itself suspended in 10 ml of dimethylformamide, and then the mixture was stirred for a further 1 hour. At the end of this time, 0.24 ml of ethyl bromoacetate and 10 ml of dimethylformamide were added, and then the whole mixture was stirred at room temperature for 3 hours. The reaction mixture was then partitioned between ethyl acetate and water, and then the organic phase was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified first by column chromatography through silica gel, eluted with a 1:1 by volume mixture of ethyl acetate and hexane, and then by recrystallization from a mixture of ethyl acetate and hexane, to give 0.38 g of the title compound in the form of plates melting at 85°-87° C.

Workup

  1. stirringthe whole mixture was stirred at room temperature for 3 hours
  2. customThe reaction mixture was then partitioned between ethyl acetate and water
  3. washthe organic phase was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified first by column chromatography through silica gel
  7. washeluted with a 1:1 by volume mixture of ethyl acetate and hexane
  8. customby recrystallization
  9. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-bd103d47539045a9b3e82919d349e109
Source dataset
uspto-grants-1997_09
Patent number
US05665752

Reaction notes

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