Pyrazole → 6-(1H-pyrazol-1-yl)pyridine-2-carbonitrile

HRID 748273Notes

Reaction equation

HRID 748273 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[N:10]1([C:2]2[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[N:11]1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1184246-Chloropyridine-2-carbonitrile

Product 1

HCID 229395546-(1H-pyrazol-1-yl)pyridine-2-carbonitrileYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-2-pyridinecarbonitrile (1.0 g, 7.2 mmol) and pyrazole (2.4 g, 35.9 mmol) were dissolved in DMF (10 ml), and potassium carbonate (3.0 g, 21.7 mmol) was added thereto. The mixture was stirred at 100° C. for 18 hrs. The reaction mixture was combined with ethyl acetate and water, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (3:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (0.98 g, 80%).

Workup

  1. washthe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washThe fractions eluted with hexane-ethyl acetate (3:1
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-58038b9cffe04c0886aa5686118476d0
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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