Imidazole → 5-(1H-imidazol-1-yl)picolinonitrile

HRID 2064231Notes

Reaction equation

HRID 2064231 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>CN(C)C=O>[N:10]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 8171545-Bromopyridine-2-carbonitrile

Product 1

HCID 671513405-(1H-imidazol-1-yl)picolinonitrileYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

5-bromopicolinonitrile (2.0 g, 10.9 mmol), imidazole (818 mg, 12 mmol) potassium carbonate (1.66 g, 12 mmol) and dimethylformamide (40 mL) were combined and heated to 130° C. for 20 hours. The reaction solution was evaporated and the residue was partitioned between dichloromethane (150 mL) and water (100 mL). The phases were separated and the organic phase was washed with water (50 mL), dried over magnesium sulfate and evaporated to give a residue which was purified by flash chromatography eluting with 2-3% methanol in dichloromethane gradient to give 5-(1H-imidazol-1-yl)picolinonitrile (1.23 g, 66%).

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between dichloromethane (150 mL) and water (100 mL)
  3. customThe phases were separated
  4. washthe organic phase was washed with water (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give a residue which
  8. customwas purified by flash chromatography
  9. washeluting with 2-3% methanol in dichloromethane gradient

Sources & evidence

ORD record
ord-aaea9b01e3a544acab1acef278e29a01
Source dataset
uspto-grants-2012_10
Patent number
US08288405B2

Reaction notes

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