Sodium hydride → HCID 44430234, compound

HRID 1394472Notes

Reaction equation

HRID 1394472 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]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=[O:22]>CN(C=O)C>[Cl:16][C:15]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[O:22])[C:7]([CH2:9][C:10]([F:12])([F:13])[F:11])=[N:6][C:5]=2[CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 116519105,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole

Product 1

HCID 44430234HCID 44430234, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (318 mg) in DMF (5 mL) was added sodium hydride (71 mg of 60% in oil dispersion). The resulting mixture was stirred at room temperature for 5 min. To the dark green solution was added 2-bromo-4′fluoroacetophenone (317 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 (10%-40% EtOAc/hexanes) to yield the title compound as a peach colored 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 (10%-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cdec3b310ec74d8ca14406d0e9f0c768
Source dataset
uspto-grants-2008_03
Patent number
US07348438B2

Reaction notes

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