反応 #45831

反応方程式

Potassium phosphate

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

phenylboronic acid

→

compound

収率 90.2%

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

収率 90.2%

溶媒

dioxane

反応条件

後処理

1. 1
   その他by purging with nitrogen
2. 2
   温度heating
3. 3
   温度under reflux for 18 hours
4. 4
   温度After cooling
5. 5
   workup.ADDITIONwater was added
6. 6
   抽出followed by extraction with ethyl acetate
7. 7
   洗浄The organic layer was washed with saturated brine
8. 8
   乾燥dried over anhydrous sodium sulfate
9. 9
   その他The solvent was evaporated away under reduced pressure
10. 10
    洗浄eluted with a mixed solvent of chloroform/methanol (2:1

実験手順

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.

出典