Potassium Carbonate → 5,6-Dichloro-1-(2-nitro-benzyl)-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole

HRID 2043267Notes

Reaction equation

HRID 2043267 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.C(=O)([O-])[O-].[K+].[K+].[N+:23]([C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28]Br)([O-:25])=[O:24]>CN(C=O)C>[Cl:16][C:15]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:28][C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=3[N+:23]([O-:25])=[O:24])[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 11430Potassium CarbonateHCID 77569alpha-Bromo-2-nitrotolueneHCID 116519105,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole

Product 1

HCID 444301765,6-Dichloro-1-(2-nitro-benzyl)-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (319 mg) in DMF (5 mL) was added potassium carbonate powder (491 mg) I) and 2-nitrobenzyl bromide (768 mg). 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%-35% EtOAc/hexanes), followed by dissolution in CH2Cl2 and trituration with hexanes to yield the title compound as orange solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customThe crude product was purified by silica gel chromatography (5%-35% EtOAc/hexanes)
  5. dissolutionfollowed by dissolution in CH2Cl2

Sources & evidence

ORD record
ord-95649c7cf77e44b3bd172926733af49d
Source dataset
uspto-grants-2013_11
Patent number
US08586616B2

Reaction notes

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