反应 #45573

反应方程式

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

2-phenyl-1,3,2-dioxaborinane

tripotassium phosphate

→

compound

收率 84.0%

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

收率 84.0%

溶剂

ethyl acetate

反应条件

后处理

1. 1
   其他by purging with nitrogen, N,N-dimethylformamide (50 ml)
2. 2
   其他was injected into it with a syringe
3. 3
   温度After cooling
4. 4
   其他the reaction liquid
5. 5
   洗涤successively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
6. 6
   干燥The organic layer was dried on anhydrous magnesium sulfate
7. 7
   浓缩the solvent was concentrated under reduced pressure
8. 8
   其他to obtain a brown residue
9. 9
   其他The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

实验过程

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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