Reacción #45573

Ecuación de reacción

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2,2-trifluoroacetamide

2-phenyl-1,3,2-dioxaborinane

tripotassium phosphate

→

compound

Rendimiento 84.0%

N-(2-Bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)2,2,2-trifluoroacetamide

Rendimiento 84.0%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroby purging with nitrogen, N,N-dimethylformamide (50 ml)
2. 2
   Otrowas injected into it with a syringe
3. 3
   TemperaturaAfter cooling
4. 4
   Otrothe reaction liquid
5. 5
   Lavadosuccessively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
6. 6
   SecadoThe organic layer was dried on anhydrous magnesium sulfate
7. 7
   Concentraciónthe solvent was concentrated under reduced pressure
8. 8
   Otroto obtain a brown residue
9. 9
   OtroThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

Procedimiento

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2,2-trifluoroacetamide (I-36) (1.29 g, 2.79 mmol), 2-phenyl-1,3,2-dioxaborinane (474 mg, 2.93 mmol), tripotassium phosphate (74-85%, 1.48 g, 5.58 mmol) and tetrakis(triphenylphosphine)palladium(0) (406 mg, 0.352 mmol) were added to a 30-ml eggplant-type flask, followed by purging with nitrogen, N,N-dimethylformamide (50 ml) was injected into it with a syringe, followed by stirring overnight at 95° C. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine, an aqueous saturated sodium hydrogencarbonate solution and saturated brine. The organic layer was dried on anhydrous magnesium sulfate, then the solvent was concentrated under reduced pressure to obtain a brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (968 mg, 84%) as a brown solid.

Fuente