3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridineacetonitrile → 3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridineethanamine

HRID 2408233Notes

Reaction equation

HRID 2408233 reaction equation
[Cl:1][C:2]1[C:3]([CH2:17][C:18]#[N:19])=[N:4][CH:5]=[C:6]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9]2)[CH:7]=1.[H][H]>CO.[Ni]>[Cl:1][C:2]1[C:3]([CH2:17][CH2:18][NH2:19])=[N:4][CH:5]=[C:6]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:16])[F:15])=[N:9]2)[CH:7]=1

Participants

5

Reactant 2

HCID 867072223-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridineacetonitrile2×HCID 178418361HCID 178418361, compound

Product 1

HCID 867072233-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridineethanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-chloro-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-pyridineacetonitrile (i.e. the product of Step B; 5.0 g, 0.017 mol) in methanol (50 mL) was shaken in a Parr hydrogenation apparatus in the presence of Raney nickel (5.0 g) and a hydrogen pressure of 50 psi (345 kPa) at room temperature for 2 h. The mixture was filtered through a pad of Celite® diatomaceous filter aid, and the filter pad was washed with dichloromethane. The filtrate was concentrated under reduced pressure to afford the title compound (2.0 g), which was used without further purification.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite® diatomaceous filter aid
  2. washthe filter pad was washed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a436766c5654e66b5e3e37e0627c609
Source dataset
uspto-grants-2014_08
Patent number
US08815772B2

Reaction notes

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