Potassium Cyanide → {6-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-yl]-3-pyridinyl}acetonitrile

HRID 1454701Notes

Reaction equation

HRID 1454701 reaction equation
[Cl:1][C:2]1[C:3]([C:21]([F:24])([F:23])[F:22])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][N:13]=3)[C:6]=2[CH:20]=1.[C-:25]#[N:26].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:21]([F:24])([F:23])[F:22])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[N:13]=[CH:14][C:15]([CH2:18][C:25]#[N:26])=[CH:16][CH:17]=3)[C:6]=2[CH:20]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 67099483HCID 67099483, compound

Product 1

HCID 67100013{6-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-yl]-3-pyridinyl}acetonitrileYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-1-[5-(chloromethyl)-2-pyridinyl]-2-ethyl-5-(trifluoromehyl)-1H-benzimidazole (from step 5, 550 mg, 1.5 mmol) in DMF (5 ml) and water (1 ml) was added KCN (470 g, 7.2 mmol) at room temperature, and then the reaction mixture was stirred for 2 h. The mixture was diluted with water and extracted with ethyl acetate/toluene (4/1) solution (3×30 ml). The organic layer was washed with water, dried (MgSO4) and concentrated. This was purified by SiO2 column chromatography developing with hexane/ethyl acetate (1/) gave 198 mg (37%) of title compound as orange oil.

Workup

  1. extractionextracted with ethyl acetate/toluene (4/1) solution (3×30 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThis was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-c10c339441e44dad97a145318ecd1158
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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