تفاعل #45831

معادلة التفاعل

Potassium phosphate

2-amino-5-bromo-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methyl-3-nitrobenzonitrile

phenylboronic acid

→

compound

المردود 90.2%

4-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-methyl-5-nitrobiphenyl-3-carbonitrile

المردود 90.2%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىby purging with nitrogen
2. 2
   درجة الحرارةheating
3. 3
   درجة الحرارةunder reflux for 18 hours
4. 4
   درجة الحرارةAfter cooling
5. 5
   workup.ADDITIONwater was added
6. 6
   استخلاصfollowed by extraction with ethyl acetate
7. 7
   غسيلThe organic layer was washed with saturated brine
8. 8
   تجفيفdried over anhydrous sodium sulfate
9. 9
   أخرىThe solvent was evaporated away under reduced pressure
10. 10
    غسيلeluted with a mixed solvent of chloroform/methanol (2:1

الإجراء التجريبي

Potassium phosphate (115 mg, 0.54 mmol) and Pd(PPh3)4 (16 mg, 5 mol %) were added to a dioxane (3 ml) solution of 2-amino-5-bromo-4-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methyl-3-nitrobenzonitrile (I-267) (100 mg, 0.27 mmol) and phenylboronic acid (40 mg, 0.33 mmol), followed by purging with nitrogen and heating under reflux for 18 hours. After cooling, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the residue was subjected to column chromatography, and eluted with a mixed solvent of chloroform/methanol (2:1, v/v) to obtain the entitled compound (89 mg, 90%) as a dark red solid.

المصدر