Dimethylformamide → HCID 89854217, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.[CH3:13][N:14](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1)#[N:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 5-bromo-N-methylpyridine-3-sulfonamide (0.1 g, 0.39 mmol) in N,N-dimethylformamide was added zinc cyanide (0.056 g, 0.47 mmol). The solution was degassed with nitrogen for 10 min, then tetrakis(triphenylphosphine)palladium(0) (30 mg) was added. The reaction mixture was heated to 100° C. for 2 h. The mixture was then diluted with water and extracted with ethyl acetate. The organic layer was dried, filtered, and concentrated under reduced pressure. The crude compound was purified by rinsing with diethyl ether to afford 5-cyano-N-methylpyridine-3-sulfonamide (60 mg) which was used without further purification.