Réaction #45803

Équation de réaction

trimethylboroxine

5-Amino-2-bromo-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

potassium carbonate

1,4-dioxane

→

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

Solvants

water

Conditions de réaction

Traitement

1. 1
   Températurecooling to room temperature
2. 2
   workup.STIRRINGby further stirring at 110° C. for 11 hours
3. 3
   TempératureAfter cooling to room temperature
4. 4
   Autrethe insoluble matter was separated by filtration
5. 5
   AutreThe organic layer was separated
6. 6
   Extractionthe aqueous layer was again extracted with ethyl acetate

Mode opératoire

5-Amino-2-bromo-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile (I-235) (2.02 g, 6.29 mmol), potassium carbonate (2.61 g, 18.87 mmol) and tetrakis(triphenylphosphine)palladium(0) (727 mg, 0.63 mmol) were dissolved in 10% water-containing 1,4-dioxane (50 ml), and at room temperature, trimethylboroxine (50 wt. % tetrahydrofuran solution, 1.90 ml, 7.55 mmol) was added. After stirring under nitrogen atmosphere at 110° C. for 8 hours and then cooling to room temperature, tetrakis(triphenylphosphine)palladium(0) (727 mg, 0.63 mmol) was added, followed by further stirring at 110° C. for 11 hours. After cooling to room temperature, the insoluble matter was separated by filtration, the filtrate was fractionated with ethyl acetate and saturated brine. The organic layer was separated, the aqueous layer was again extracted with ethyl acetate.

Source