Ethyl bromoacetate → HCID 59682295, compound

HRID 1394476Notes

Reaction equation

HRID 1394476 reaction equation
[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]2[NH:6][C:7]([CH2:9][C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[C:15]([Cl:16])=[CH:14][C:5]=2[N:6]=[C:7]1[CH2:9][C:10]([F:12])([F:13])[F:11])[CH3:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 116519105,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole

Product 1

HCID 59682295HCID 59682295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (1 g) in DMF (5 mL) was added sodium hydride (85 mg of 60% in oil dispersion). The resulting mixture was stirred at room temperature for 5 min. To the dark green solution was added ethyl bromoacetate (363 mg) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with water, extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (5%-30% EtOAc/hexanes) to yield the title compound as a yellow solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by silica gel chromatography (5%-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-453061c4dd6f45c99744ffbd16b6e6a5
Source dataset
uspto-grants-2008_03
Patent number
US07348438B2

Reaction notes

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