Methanol → HCID 21717349, compound

Participants

Reaction Steps

A mixture of 8-amino-6-chloro-2,3-dimethylimidazo[1,2-a]pyridine (0.894 g, 4.57 mmol), 2,6-dimethylbenzaldehyde (0.77 g, 5.7 mmol), ZnCl2 (1.08 g, 7.92 mmol), NaB(CN)H3 (0.36 g, 5.7 mmol) and MeOH (35 ml) was refluxed for 3.5 h. More 2,6-dimethylbenzaldehyde (0.25 g in 4 ml MeOH), ZnCl2 (0.55 g) and NaB(CN)H3 (0.35 g) were added. The reaction mixture was refluxed for additional 4 h. Subsequent workup by addition of 1 M NaOH (150 ml), and water (50 ml), followed by extraction of the mixture with CH2Cl2, drying, and evaporation of solvent gave a solid residue. The crude product dissolved in ethyl acetate and ether was added. Filtration and evaporation of solvent gave a residue which was recrystallized from ethyl acetate to give 0.52 g product.

Provenance & Evidence