5-Bromo-2,3-dimethoxypyridine → 5,6-Dimethoxypyridine-3-carbonitrile

HRID 1675949Notes

Reaction equation

HRID 1675949 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[Cu][C:13]#[N:14]>CN(C)C=O>[CH3:11][O:10][C:4]1[C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]([CH:3]=1)[C:13]#[N:14]

Participants

4

Reactant 2

HCID 125630845-Bromo-2,3-dimethoxypyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 467367595,6-Dimethoxypyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 5-bromo-2,3-dimethoxypyridine (7-2, 0.300 g, 1.38 mmol, 1.0 equiv) in dimethylformamide (3.9 mL) was added copper (I) cyanide (0.15 g, 1.65 mmol, 1.2 equiv) and the reaction mixture was heated for 40 minutes at 180° C. in a microwave reactor. The reaction mixture was cooled and partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with water (2×30 mL) and brine (1×30 mL), dried over magnesium sulfate and concentrated. The residue was purified via normal phase chromatography (0 to 40% EtOAc in hexanes, silica) to afford the desired product (7-3) as white solid after concentration. ESI+MS [M+H]+ C8H8N2O2 calc'd 165.1, found 165.1.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between EtOAc (50 mL) and water (50 mL)
  3. washThe organic phase was washed with water (2×30 mL) and brine (1×30 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified via normal phase chromatography (0 to 40% EtOAc in hexanes, silica)

Sources & evidence

ORD record
ord-705f7fee70e246cf8fc3d3a01c3a89a8
Source dataset
uspto-grants-2011_08
Patent number
US08003797B2

Reaction notes

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