Phosphorus oxychloride → HCID 20251887, compound

Participants

Reaction Steps

To a solution of 3-amino-2-anilinopyridine (2.0 g) and 2-(imidazol-1-yl)acetic acid (1.56 g) in pyridine (20 ml) was dropwise added phosphorus oxychloride (1.91 g) and the mixture was refluxed for 30 minutes. The reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate. The combined extract was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was removed under reduced pressure to give a residue, which was subjected to column chromatography on silica gel (20 g) eluting with a mixture of dichloromethane and ethanol. The fractions containing the desired compound were combined and evaporated in vacuo. The resultant crystal was recrystallized from a mixture of ethyl acetate and n-hexane to give 2-(imidazol-1-yl)methyl-3-phenyl-3H-imidazo[4,5-b]pyridine (0.8 g).

Provenance & Evidence