反応 #45581

反応方程式

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

phenylboronic acid

potassium phosphate

→

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

溶媒

1,4-dioxane

water

反応条件

後処理

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

実験手順

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.

出典