5-bromo-2-methyl-3H-imidazo[4,5-b]pyridine → HCID 178432171, compound
Reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH3:11])[NH:10][C:5]2=[CH:4][CH:3]=1.[Cu][C:13]#[N:14]>CN(C)C=O>[CH3:11][C:9]1[N:8]=[C:6]2[NH:7][C:2]([C:13]#[N:14])=[CH:3][CH:4]=[C:5]2[N:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a solution of 5-bromo-2-methyl-1H-imidazo[4,5-b]pyridine (1.92 g) in N,N-dimethylformamide (48 ml) was added Copper (I) cyanide (2.04 g), and the mixture was stirred for 9 hr at 150° C. After evaporation of the solvent under reduced pressure, water (45 ml) and ethylenediamine (2.7 g) were added to the residue, and the mixture was heated at 70° C. for 15 min. The solution was concentrated under reduced pressure and the residue was purified by a short silica gel column to give the objective compound (927 mg) as a brown powder. Purification by silica gel column chromatography (dichloromethane/methanol=10/1) gave a purer compound.