Reacción #80193

Ecuación de reacción

Ethyl 2-chloro-nicotinate

4-trifluoromethylphenylboronic acid

sodium carbonate

→

brown oil

Rendimiento 109.7%

2-(4-Trifluoromethyl-phenyl)-nicotinic acid ethyl ester

Rendimiento 109.7%

Disolventes

dimethoxyethane

dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction vessel purged
2. 2
   TemperaturaThe reaction mixture was heated at 90 C
3. 3
   Temperaturafor 1.5 h before being cooled
4. 4
   Extracciónextracted with 150 ml of ether
5. 5
   LavadoThe organic layer was washed with 50 ml of 2N NaOH, 2×50 ml water, and brine
6. 6
   Secadobefore being dried (magnesium sulfate)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under vacuum

Procedimiento

Ethyl 2-chloro-nicotinate (1.86 g, 10.0 mmol) was dissolved in 10 ml of dimethoxyethane. Tetrakis(triphenylphosphine)palladium (347 mg, 0.3 mmol) was added and the reaction vessel purged by alternating vacuum and nitrogen gas three times. A solution of 4-trifluoromethylphenylboronic acid (2.09 g, 11.0 mmol) in 20 ml of dimethoxyethane was added to the reaction mixture followed by 10 ml of a 2M sodium carbonate solution. The reaction mixture was heated at 90 C. for 1.5 h before being cooled and extracted with 150 ml of ether. The organic layer was washed with 50 ml of 2N NaOH, 2×50 ml water, and brine before being dried (magnesium sulfate), filtered and concentrated under vacuum to afford 3.24 g of a brown oil. This material was purified by silica gel chromatography eluting with 5 to 10% ethyl acetate in hexanes to afford 2.34 g of the title compound as a pale yellow oil.

Fuente