Reacción #45700

Ecuación de reacción

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

diisopropylethylamine

ethyl azetidine-3-carboxylate hydrochloride

→

Ethyl 1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidine-3-carboxylate

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter heated
2. 2
   Temperaturaunder reflux for 3 hours
3. 3
   LavadoAfter washing with water
4. 4
   Secadodrying over anhydrous sodium sulfate
5. 5
   Otrothe solvent was evaporated away under reduced pressure
6. 6
   Otrothe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70:1)
7. 7
   Otroto obtain a brown oil (0.60 g, quant)

Procedimiento

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.45 g, 1.57 mmol) was dissolved in dichloromethane (15 ml), then diisopropylethylamine (0.6 ml, 3.53 mmol) and ethyl azetidine-3-carboxylate hydrochloride (I-147) (0.55 g) were added. After heated under reflux for 3 hours, this was diluted with dichloromethane. After washing with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70:1) to obtain a brown oil (0.60 g, quant).

Fuente