Réaction #61798

Équation de réaction

cesium carbonate

4-(trifluoromethyl)phenyl boronic acid

methyl-5-bromo-pyridine-3-carboxylate

→

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

Rendement 76.8%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   Filtrationfiltered
3. 3
   Autrethe filtrate evaporated
4. 4
   Lavagewashed twice with water
5. 5
   Séchagedried over sodium sulphate
6. 6
   Autreevaporated

Mode opératoire

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

Source