5-Bromo-2,3-dimethoxypyridine → 5,6-Dimethoxypyridine-3-carbonitrile
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
Product 1
Reagents, catalysts & solvents 1
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.