Methanol → 5-(Imidazo[1,2-a]pyridin-6-yl)-2-methoxy-6-methyl-3-pyridinecarbonitrile

Reaction equation

C(Cl)Cl.Cl[C:5]1[C:10]([C:11]#[N:12])=[CH:9][C:8]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([CH:19]=[CH:20][N:21]=3)[CH:18]=2)=[C:7]([CH3:22])[N:6]=1.[CH3:23][OH:24]>>[N:21]1[CH:20]=[CH:19][N:17]2[CH:18]=[C:13]([C:8]3[CH:9]=[C:10]([C:11]#[N:12])[C:5]([O:24][CH3:23])=[N:6][C:7]=3[CH3:22])[CH:14]=[CH:15][C:16]=12

Participants

Reactant 3

HCID 887Methanol

HCID 6344Dichloromethane

HCID 138523142-Chloro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methylpyridine-3-carbonitrile

Product 1

HCID 138523345-(Imidazo[1,2-a]pyridin-6-yl)-2-methoxy-6-methyl-3-pyridinecarbonitrile

Procedure

In a solvent mixture of 30 ml of methylene chloride and 30 ml of methanol, 0.59 g of 2-chloro-5-(imidazo[1,2-a]pyridin-6-yl)-6-methyl-3-pyridinecarbonitrile described above was stirred under reflux for 3 hours. After cooling, the solvent was removed by distillation and chloroform-water was added to the residue. The chloroform was taken by fractionation. After washing with water and drying over magnesium sulfate, chloroform was removed by distillation under reduced pressure. The residue was recrystallized from benzene-n-hexane to obtain 0.75 g of 5-(imidazo[1,2-a]pyridin-6-yl)-2-methoxy-6-methyl-3-pyridinecarbonitrile.