Реакция #45581

Уравнение реакции

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

phenylboronic acid

potassium phosphate

→

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

Растворители

1,4-dioxane

water

Условия реакции

Обработка

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

Методика

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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