Réaction #45700

Équation de réaction

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

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source