Methanol → 4,6-dichloro-2,3-dimethyl-3H-imidazo[4,5-c]pyridine
Reaction equation
ClC1C(NC)=C(N)C=C(Cl)N=1.[Cl:12][C:13]1[C:18]2[N:19]([CH3:24])[C:20]([CH3:23])(O)[NH:21][C:17]=2[CH:16]=[C:15]([Cl:25])[N:14]=1.CO.CC1C=CC(S(O)(=O)=O)=CC=1>CC(O)=O>[Cl:12][C:13]1[C:18]2[N:19]([CH3:24])[C:20]([CH3:23])=[N:21][C:17]=2[CH:16]=[C:15]([Cl:25])[N:14]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2,6-dichloro-N3-methylpyridine-3,4-diamine 2.45 (0.15 g, 0.78 mmol) was dissolved in AcOH (5 mL) and heated in a sealed tube at 100° C. After 48 hr, LC/MS indicated full conversion to desired intermediate 4,6-dichloro-2,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-c]pyridin-2-ol 2.46. Reaction mixture was evaporated under reduced pressure and re-dissolved with MeOH (3 mL), 4-methylbenzenesulfonic acid (220 mg, 1.2 mmol) was added and mixture heated at 120° C. in a microwave reactor. After 20 min, LC/MS indicated full conversion to desired product. Solvent was removed under reduced pressure, and solids were diluted and extracted with ethyl acetate and water. The organic layer was washed with water and brine. Organic phase was then dried over MgSO4, and evaporated under reduced pressure to obtain 4,6-dichloro-2,3-dimethyl-3H-imidazo[4,5-c]pyridine 2.47 that was used for next step without further purification.
Workup
- customReaction mixture
- customwas evaporated under reduced pressure
- additionwas added
- temperaturemixture heated at 120° C. in a microwave reactor
- waitAfter 20 min
Sources & evidence
- ORD record
- ord-2a3b331b98624a00b8f98935d808a1fb
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376441B2
Reaction notes
Loading…