Reaktion #45581

Reaktionsgleichung

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

phenylboronic acid

potassium phosphate

→

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

Lösungsmittel

1,4-dioxane

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle