Reaction #45700

Reaction equation

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

Solvents

dichloromethane

dichloromethane

Conditions

Workup

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

Procedure

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