Reaktion #45628

Reaktionsgleichung

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

7-Fluoro-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrile

→

compound

Ausbeute 65.0%

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

Ausbeute 65.0%

Lösungsmittel

water

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   WaschenThe organic layer was washed with saturated brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   SonstigeThe solvent was evaporated away
5. 5
   Wascheneluted with a mixed solvent of chloroform/methanol (50:1
6. 6
   Sonstigev/v), recrystallized
7. 7
   Sonstigepurified with n-hexane/ethyl acetate

Vorschrift

7-Fluoro-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrile (I-92) (200 mg, 0.56 mmol) was dissolved in dimethylsulfoxide (2 ml), triethylamine (190 μl, 1.35 mmol) and (3S)-3-(dimethylamino)pyrrolidine (86 μl, 0.68 mmol) were added, followed by stirring at 90° C. for 15 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (50:1, v/v), recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (163 mg, 65%) as a yellow solid.

Quelle