HCID 67099131, compound → HCID 23125737, compound

HRID 2077773Notes

Reaction equation

HRID 2077773 reaction equation
[Cl:1][C:2]1[C:3]([C:22]([F:25])([F:24])[F:23])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][C:19]#[N:20])=[N:16][CH:17]=3)[C:6]=2[CH:21]=1>N.C(O)C.[Ni]>[Cl:1][C:2]1[C:3]([C:22]([F:23])([F:24])[F:25])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][NH2:20])=[N:16][CH:17]=3)[C:6]=2[CH:21]=1

Participants

4

Reactant 1

HCID 67099131HCID 67099131, compound

Product 1

HCID 23125737HCID 23125737, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

To a solution of {5-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-1-yl]-2-pyridinyl}acetonitrile (step 4, 1.0 g, 2.8 mmol), in ammonia-ethanol (30 ml) was added Raney-Ni and stirred for 8 h under hydrogen atmosphere (3.0 kgf/cm2). The catalyst was filtered off and the solvent was removed. The residue was diluted with ethyl acetate, washed with brine, dried (MgSO4) and concentrated to give 813 mg of title compound as black solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8a8223903243425abc71b40c3e412982
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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