反应 #45581

反应方程式

2-amino-5-bromo-4-fluoro-3-methoxy-6-methylbenzonitrile

phenylboronic acid

potassium phosphate

→

4-Amino-3-cyano-6-fluoro-5-methoxy-2-methylbiphenyl

溶剂

1,4-dioxane

water

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   温度After cooling
3. 3
   其他the insoluble matter was separated by filtration through Celite
4. 4
   其他the reaction solvent was evaporated away under reduced pressure
5. 5
   workup.DISSOLUTIONThe resulting residue was dissolved in ethyl acetate
6. 6
   洗涤washed with water and saturated brine
7. 7
   干燥the organic layer was dried over anhydrous sodium sulfate
8. 8
   其他the solvent was evaporated away under reduced pressure
9. 9
   洗涤eluted wrath a mixed solvent of n-hexane/ethyl acetate (3:1
10. 10
    其他v/v) to obtain the entitled compound (20.12 g, quant) as a yellow white solid

实验过程

Under nitrogen atmosphere, 2-amino-5-bromo-4-fluoro-3-methoxy-6-methylbenzonitrile (I-45) (20.0 g, 77.20 mmol), phenylboronic acid (11.3 g, 92.64 mmol), potassium phosphate (34.4 g, 162.11 mmol) were dissolved in a mixed liquid of 1,4-dioxane (400 ml) and water (20 ml), tetrakis(triphenylphosphine)palladium (2.6 g, 2.32 mmol) was added, followed by stirring at 110° C. for 15 hours. After cooling, the insoluble matter was separated by filtration through Celite, the reaction solvent was evaporated away under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with water and saturated brine, the organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, eluted wrath a mixed solvent of n-hexane/ethyl acetate (3:1, v/v) to obtain the entitled compound (20.12 g, quant) as a yellow white solid.

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