Reacción #60541

Ecuación de reacción

sodium carbonate

5-fluoro-2-methoxyphenylboronic acid

4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

1,2-dimethoxyethane

→

title compound

Rendimiento 127.3%

4-(5-Fluoro-2-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester

Rendimiento 127.3%

Disolventes

Brine

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
2. 2
   Concentraciónthe filtrate was concentrated
3. 3
   Otroto give a residue, which
4. 4
   Otrowas purified by silica gel column chromatography (ethyl acetate/heptane)

Procedimiento

To a mixture of 5-fluoro-2-methoxyphenylboronic acid (1 g, 5.88 mmol), 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (4.22 g, 7.64 mmol) (David J. Wustrow, Lawrence D. Wise, Synthesis, 1991, 993) and 1,2-dimethoxyethane (30 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.34 g, 0.29 mmol) and 2N aqueous solution of sodium carbonate (8.82 mL, 17.6 mmol), followed by stirring for 2 hours at an external temperature of 90° C. under a nitrogen atmosphere. Brine was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the filtrate was concentrated to give a residue, which was purified by silica gel column chromatography (ethyl acetate/heptane) to give 2.3 g of the title compound as a yellow oil.

Fuente