Reaktion #45783

Reaktionsgleichung

(3S)-3-(Dimethylamino)pyrrolidine

triethylamine

7-fluoro-2-(2-hydroxyphenyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

Ausbeute 24.7%

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-2-(2-hydroxyphenyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 24.7%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe system was purged with nitrogen
2. 2
   Sonstigesealed up
3. 3
   TemperaturAfter cooling
4. 4
   Sonstigethe solvent was evaporated away under reduced pressure
5. 5
   workup.DISSOLUTIONthe resulting residue was dissolved in chloroform
6. 6
   Waschenwashed with water and saturated brine
7. 7
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
8. 8
   Sonstigethe solvent was evaporated away under reduced pressure
9. 9
   WaschenElution with a mixed solvent of chloroform/methanol (97:3
10. 10
    Sonstigev/v) gave a main product
11. 11
    WaschenThis was washed with a mixed solvent of isopropyl ether and ethanol
12. 12
    Filtrationthe solid was collected by filtration

Vorschrift

(3S)-3-(Dimethylamino)pyrrolidine (100 μl, 0.79 mmol) and triethylamine (220 μl) were added to a dimethyl sulfoxide (5 ml) solution of 7-fluoro-2-(2-hydroxyphenyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-212) (204 mg, 0.59 mmol). The system was purged with nitrogen, then sealed up, and heated at 120° C. for 30 minutes. After cooling, the solvent was evaporated away under reduced pressure, then the resulting residue was dissolved in chloroform, and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, and the resulting residue was subjected to silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (97:3, v/v) gave a main product. This was washed with a mixed solvent of isopropyl ether and ethanol, and the solid was collected by filtration to obtain the entitled compound (64 mg, 24%) as a pale yellow solid.

Quelle