Reacción #412244

Ecuación de reacción

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester

Trifluoromethanesulfonic acid 6-cyano -naphthalen-2-yl ester

triphenylphosphine

triethylamine

methanol

DMF

→

desired product

Rendimiento 50.0%

6-Cyano-naphthalene-2-carboxylic acid methyl ester

Rendimiento 50.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThis mixture was purged with carbon monoxide for ten minutes
2. 2
   workup.ADDITIONThe mixture was then diluted with brine
3. 3
   Extracciónextracted with EtOAc (3×100 mL)
4. 4
   Lavadoextracts washed with 1N HCl (2×100 mL)
5. 5
   Secadodried over MgSO4
6. 6
   Concentraciónconcentrated under reduced pressure

Procedimiento

To a solution of trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester from Example 95 (1.50 g, 4.98 mmol) in 20 mL of anhydrous DMF was added palladium(II) acetate (33.53 mg, 0.15 mmol), triphenylphosphine (78.36 mg, 0.30 mmol), triethylamine (1.39 mL, 9.96 mmol) and 5 mL of methanol. This mixture was purged with carbon monoxide for ten minutes. The reaction mixture was then placed under balloon pressure of carbon monoxide and heated to 60° C. for 16 hours. The mixture was then diluted with brine, extracted with EtOAc (3×100 mL), extracts washed with 1N HCl (2×100 mL), dried over MgSO4, and concentrated under reduced pressure. Flash chromatography (hexane to 20% EtOAc/hexane) afforded the desired product as a white solid (525 mg, 50%).

Fuente