Reacción #45754

Ecuación de reacción

Diisopropylethylamine

2-(methylamino)pyridine

dichloromethane

2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile

→

compound

Rendimiento 57.7%

7-Fluoro-5-methyl-2-[methyl(pyridin-2-yl)amino]-6-phenyl-1,3-benzoxazole-4-carbonitrile

Rendimiento 57.7%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby heating
2. 2
   OtroThe reaction liquid
3. 3
   workup.ADDITIONwas added
4. 4
   Lavadoby washing with water (50 ml) and saturated brine (50 ml)
5. 5
   SecadoAfter drying over anhydrous sodium sulfate and concentration under reduced pressure
6. 6
   Otrothe resulting residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1)

Procedimiento

Diisopropylethylamine (169 μl, 0.944 mmol) and 2-(methylamino)pyridine (102 μl, 0.994 mmol) were added to a dichloromethane (10 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (190 mg, 0.663 mmol), followed by heating under reflux in an oil bath at 50° C. for 3 hours. The reaction liquid was cooled to room, temperature, ethyl acetate (70 ml) was added, followed by washing with water (50 ml) and saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1) to obtain the entitled compound (137 mg, 57.5%) as a colorless solid.

Fuente