Reaktion #45696

Reaktionsgleichung

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

diisopropylethylamine

3-hydroxy-1-azetidine hydrochloride

→

7-Fluoro-2-(3-hydroxyazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby heating
2. 2
   Temperaturunder reflux in a sealed tube under nitrogen atmosphere for 6 hours
3. 3
   TemperaturAfter cooling
4. 4
   Waschendilution with methylene chloride and washing with water and saturated brine
5. 5
   Trocknenthe organic layer was dried over anhydrous sodium sulfate
6. 6
   Sonstigethe solvent was evaporated away under reduced pressure
7. 7
   SonstigeThe resisting residue was recrystallized
8. 8
   Sonstigepurified with n-hexane/ethyl acetate
9. 9
   Sonstigeto obtain the entitled compound (123 mg, quant) as a yellow white solid

Vorschrift

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (100 mg, 0.35 mmol) was dissolved in methylene chloride (2 ml), then diisopropylethylamine (237 μl, 1.39 mmol) and 3-hydroxy-1-azetidine hydrochloride (76 mg, 0.70 mmol) were added, followed by heating under reflux in a sealed tube under nitrogen atmosphere for 6 hours. After cooling, dilution with methylene chloride and washing with water and saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resisting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (123 mg, quant) as a yellow white solid.

Quelle