Reaction #45549

Reaction equation

N,N-dimethylformamide

N-(3-bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

trans-β-styreneboronic acid

→

N-(3-Bromo-6-cyano-2-methoxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide

Solvents

ethyl acetate

Conditions

Workup

1. 1
   OtherThe reaction liquid
2. 2
   Temperaturewas cooled
3. 3
   Washby washing with saturated brine (30 ml×2)
4. 4
   Dryingdrying over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrating under reduced pressure

Procedure

Tetrakis(triphenylphosphine)palladium(0) (6.4 mg, 5.5 μmol) was added to an N,N-dimethylformamide (1.0 ml) suspension of N-(3-bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide (I-6) (50 mg, 111 μmol), trans-β-styreneboronic acid (17.2 mg, 116 μmol), potassium phosphate n-hydrate (74-78%, 64 mg, 222 μmol), followed by stirred overnight at 95° C. The reaction liquid was cooled, then ethyl acetate (30 ml) was added, followed by washing with saturated brine (30 ml×2), drying over anhydrous magnesium sulfate, concentrating under reduced pressure.

Source