Methyl iodide → 4-Bromo-1-methyl-1H-pyrazole-3-carbonitrile

HRID 1865051Notes

Reaction equation

HRID 1865051 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([C:9]#[N:10])=[N:6][NH:7][CH:8]=1.[CH3:11]I>CN(C=O)C>[Br:3][C:4]1[C:5]([C:9]#[N:10])=[N:6][N:7]([CH3:11])[CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27356234-Bromo-1H-pyrazole-3-carbonitrile

Product 1

HCID 455943224-Bromo-1-methyl-1H-pyrazole-3-carbonitrileYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (60 wt % oil dispersion, 700 mg, 17.5 mmol) in several portions under a nitrogen purge to a solution of 4-bromo-1H-pyrazole-3-carbonitrile (2.0 g, 11.6 mmol) in 15 mL of anhydrous DMF at 0° C. Stir the reaction at 0° C. for one hour. Add methyl iodide (0.9 mL, 14.5 mmol) to the mixture and allow to stir and come to room temperature over 1 hour. Pour into 100 mL of ice-water and stir for 15 minutes. Filter off the resulting solid and rinse with 20 mL of water. Dry the solid overnight. Chromatograph (1/9-1/3 EtOAc/hexanes) over silica gel to give the title compound as a white solid (1.38 g, 63%), along with a small amount (100 mg) of the regioisomeric bromide.

Workup

  1. customthe reaction at 0° C. for one hour
  2. stirringto stir
  3. stirringstir for 15 minutes
  4. filtrationFilter off the resulting solid
  5. washrinse with 20 mL of water
  6. customDry the solid overnight

Sources & evidence

ORD record
ord-ac0ab512ba064c66b85bcda4067b29d0
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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