Reacción #979945

Ecuación de reacción

3-amino-4-(4'-cyanophenyl)aminopyridine

propionic anhydride

sodium bicarbonate

→

title compound

Rendimiento 22.0%

1-(4-Cyanophenyl)-2-ethylimidazo[4,5-c]pyridine

Rendimiento 22.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawere heated together under nitrogen
2. 2
   Temperaturaat reflux for 17 hours
3. 3
   Extracciónthe product was extracted into dichloromethane (3×150 ml)
4. 4
   SecadoThe combined extracts were dried (MgSO4)
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   Otrothe residue was purified by flash chromatography (gradient elution with ethyl acetate/methanol)

Procedimiento

A mixture of 3-amino-4-(4'-cyanophenyl)aminopyridine (Preparation 26(b)) (2.00 g, 9.5 mmol) and propionic anhydride (12.2 ml, 95 mmol) were heated together under nitrogen at reflux for 17 hours. The resulting solution was treated with excess aqueous sodium bicarbonate and the product was extracted into dichloromethane (3×150 ml). The combined extracts were dried (MgSO4), concentrated under reduced pressure, and the residue was purified by flash chromatography (gradient elution with ethyl acetate/methanol) to give the title compound as a brown solid (510 mg, 22%).

Fuente