تفاعل #45783

معادلة التفاعل

(3S)-3-(Dimethylamino)pyrrolidine

triethylamine

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

→

compound

المردود 24.7%

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

المردود 24.7%

المذيبات

dimethyl sulfoxide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe system was purged with nitrogen
2. 2
   أخرىsealed up
3. 3
   درجة الحرارةAfter cooling
4. 4
   أخرىthe solvent was evaporated away under reduced pressure
5. 5
   workup.DISSOLUTIONthe resulting residue was dissolved in chloroform
6. 6
   غسيلwashed with water and saturated brine
7. 7
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
8. 8
   أخرىthe solvent was evaporated away under reduced pressure
9. 9
   غسيلElution with a mixed solvent of chloroform/methanol (97:3
10. 10
    أخرىv/v) gave a main product
11. 11
    غسيلThis was washed with a mixed solvent of isopropyl ether and ethanol
12. 12
    ترشيحthe solid was collected by filtration

الإجراء التجريبي

(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.

المصدر