5-Bromo-2-methoxy-3-methylpyridine → 6-Methoxy-5-methylnicotinonitrile

HRID 1753218Notes

Reaction equation

HRID 1753218 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:11]([Cu])#[N:12]>CN(C=O)C.CCOC(C)=O>[C:11]([C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1)#[N:12]

Participants

5

Reactant 2

HCID 225911765-Bromo-2-methoxy-3-methylpyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 534159886-Methoxy-5-methylnicotinonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-2-methoxy-3-methyl-pyridine (1.0 g, 5.0 mmol) in DMF (10 ml) was added CuCN (0.534 g, 6.0 mmol) and the resulting mixture is heated at reflux for 28 h. After cooling to room temperature the mixture is diluted with EtOAc and washed with 10% ammonia solution followed by water and brine solution. The organic layer was separated, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by flash chromatography (5% EtOAc/Hexane) to give 5-cyano-2-methoxy-3-methyl-pyridine (36) (0.68 g, 93%).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 28 h
  3. washwashed with 10% ammonia solution
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (5% EtOAc/Hexane)

Sources & evidence

ORD record
ord-3331207347604db1bc03788b882b2c3f
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

Loading…