Reaction #45588

Reaction equation

potassium carbonate

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

→

compound

Yield 87.2%

4-Amino-3′-benzyloxy-3-cyano-6-fluoro-5-methoxy-2-methylbiphenyl

Yield 87.2%

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Othermethanol was evaporated away under reduced pressure, saturated brine (50 ml)
3. 3
   workup.ADDITIONwas added
4. 4
   Extractionthe product was extracted with ethyl acetate (50 ml×2)
5. 5
   DryingThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Procedure

Aqueous potassium carbonate solution (20% w/v, 6.07 ml), methanol (12.1 ml) were added to N-(3′-benzyloxy-5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2,2-trifluoroacetamide (I-53) (400 mg, 873 μmol), followed by stirring overnight at 70° C. After cooling, methanol was evaporated away under reduced pressure, saturated brine (50 ml) was added, the product was extracted with ethyl acetate (50 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (276 mg, 87%) as a colorless solid.

Source