Reaction #45587

Reaction equation

N,N-dimethylformamide

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

3-benzyloxyphenylboronic acid

→

compound

Yield 73.0%

N-(3′-Benzyloxy-5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2,2-trifluoroacetamide

Yield 73.0%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   OtherThe reaction liquid
2. 2
   Temperaturewas cooled
3. 3
   Washby washing with saturated brine (50 ml×3)
4. 4
   Dryingdrying over anhydrous magnesium sulfate, concentration under reduced pressure
5. 5
   OtherThe residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1), (n-hexane:ethyl acetate=6:1)

Procedure

Tetrakis(triphenylphosphine)palladium(0) (287 mg, 249 μmol) was added to an N,N-dimethylformamide (16.5 ml) suspension of N-(2-cyano-5-fluoro-4-iodo-6-methoxy-3-methylphenyl)-2,2,2-trifluoroacetamide (I-35) (500 mg, 1.24 mmol), 3-benzyloxyphenylboronic acid (425 mg, 1.87 mmol), potassium phosphate n-hydrate (74-78%, 713 mg, 2.49 mmol), followed by stirring at 95° C. for 5.5 hours. The reaction liquid was cooled, then ethyl acetate (100 ml) was added, followed by washing with saturated brine (50 ml×3), drying over anhydrous magnesium sulfate, concentration under reduced pressure. The residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1), (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (415 mg, 73%) as a yellow solid.

Source