Dimethylformamide → 5-Bromo-3-methylpyridine-2-carbonitrile

HRID 339980Notes

Reaction equation

HRID 339980 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH3:10][N:11](C)C=O.[Cu](C#N)C#N>>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([C:10]#[N:11])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418260HCID 178418260, compound

Product 1

HCID 207750075-Bromo-3-methylpyridine-2-carbonitrileYield 49.4%

Conditions

Temperature
120 °C

Procedure

To a solution of 2,5-dibromo-3-methylpyridine (5.0 g, 20. mmol) in N,N-dimethylformamide (20.0 mL, 259 mmol) was added copper cyanide (1.8 g, 20. mmol) and the reaction was stirred at 120° C. for 12 h. The reaction was partitioned between EtOAc and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated and purified by combi-flash chromatography to afford 1.94 g (49% yield) of the desired product as a white solid.

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by combi-flash chromatography

Sources & evidence

ORD record
ord-52a681ab55184b49a6001931513cf1c5
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

Loading…