Реакция #45573

Уравнение реакции

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

2-phenyl-1,3,2-dioxaborinane

tripotassium phosphate

→

compound

Выход 84.0%

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

Выход 84.0%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   Другоеby purging with nitrogen, N,N-dimethylformamide (50 ml)
2. 2
   Другоеwas injected into it with a syringe
3. 3
   ТемператураAfter cooling
4. 4
   Другоеthe reaction liquid
5. 5
   Промывкаsuccessively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
6. 6
   СушкаThe organic layer was dried on anhydrous magnesium sulfate
7. 7
   Концентрированиеthe solvent was concentrated under reduced pressure
8. 8
   Другоеto obtain a brown residue
9. 9
   ДругоеThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

Методика

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.

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