Ethyl bromoacetate → HCID 19089097, compound

HRID 1463986Notes

Reaction equation

HRID 1463986 reaction equation
[H-].[Na+].[NH:3]1[C:10]2[N:6]([N:7]=[CH:8][CH:9]=2)[CH:5]=[CH:4]1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(OCC)(=O)C>CN(C)C=O.O>[CH2:16]([O:15][C:13]([CH2:12][N:3]1[C:10]2[N:6]([N:7]=[CH:8][CH:9]=2)[CH:5]=[CH:4]1)=[O:14])[CH3:17]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178419859HCID 178419859, compound

Product 1

HCID 19089097HCID 19089097, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 62% sodium hydride (7.23 g) in N,N-dimethylformamide (70 ml) was added 1H-imidazo[1,2-b]-pyrazole (20 g) by portions under ice-cooling. A solution of ethyl bromoacetate (20.7 ml) in N,N-dimethylformamide (50 ml) was added thereto at the same condition. The mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into a mixture of ethyl acetate (1 l) and water (500 ml). The separated organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated and the residue was subjected to column chromatography on silica gel using ethyl acetate as an eluent. Fractions containing the object compound were combined and evaporated in vacuo to give 1-ethoxycarbonylmethyl-1H-imidazo[1,2-b]pyrazole (25 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. additionFractions containing the object compound
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f4c0a2fe026443de90ae0968234eeaa1
Source dataset
uspto-grants-1994_04
Patent number
US05302712

Reaction notes

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