Reacción #61798

Ecuación de reacción

cesium carbonate

4-(trifluoromethyl)phenyl boronic acid

methyl-5-bromo-pyridine-3-carboxylate

→

5-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester

Rendimiento 76.8%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   Filtraciónfiltered
3. 3
   Otrothe filtrate evaporated
4. 4
   Lavadowashed twice with water
5. 5
   Secadodried over sodium sulphate
6. 6
   Otroevaporated

Procedimiento

81 mg (0.07 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 1.0 g (4.63 mmol) methyl-5-bromo-pyridine-3-carboxylate in 23 ml N,N-dimethylformamide and the mixture was heated to 80° C. Then 2.26 g (6.94 mmol) cesium carbonate and 0.97 g (5.09 mmol) of 4-(trifluoromethyl)phenyl boronic acid were added and the mixture was stirred at 80° C. over night. The reaction mixture was cooled to room temperature, filtered, and the filtrate evaporated. The residue was taken up with ethyl acetate, washed twice with water, dried over sodium sulphate and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 1.0 g (68%) of 5-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester

Fuente