반응 #45831

반응 방정식

Potassium phosphate

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

phenylboronic acid

→

compound

수율 90.2%

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

수율 90.2%

용매

dioxane

반응 조건

후처리

1. 1
   기타by purging with nitrogen
2. 2
   온도heating
3. 3
   온도under reflux for 18 hours
4. 4
   온도After cooling
5. 5
   workup.ADDITIONwater was added
6. 6
   추출followed by extraction with ethyl acetate
7. 7
   세척The organic layer was washed with saturated brine
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   기타The solvent was evaporated away under reduced pressure
10. 10
    세척eluted with a mixed solvent of chloroform/methanol (2:1

실험 절차

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.

출처