Reaction #45573

Reaction equation

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

2-phenyl-1,3,2-dioxaborinane

tripotassium phosphate

→

compound

Yield 84.0%

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

Yield 84.0%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Otherby purging with nitrogen, N,N-dimethylformamide (50 ml)
2. 2
   Otherwas injected into it with a syringe
3. 3
   TemperatureAfter cooling
4. 4
   Otherthe reaction liquid
5. 5
   Washsuccessively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
6. 6
   DryingThe organic layer was dried on anhydrous magnesium sulfate
7. 7
   Concentrationthe solvent was concentrated under reduced pressure
8. 8
   Otherto obtain a brown residue
9. 9
   OtherThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

Procedure

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.

Source