Reaktion #61795

Reaktionsgleichung

cesium carbonate

4-(trifluoromethoxy)phenylboronic acid

methyl-6-bromo-pyridine-2-carboxylate

→

6-(4-Trifluoromethoxy-phenyl)-pyridine-2-carboxylic acid methyl ester

Ausbeute 44.7%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Filtrationfiltered
3. 3
   Sonstigethe filtrate evaporated
4. 4
   Waschenwashed twice with water
5. 5
   Trocknendried over sodium sulphate
6. 6
   Sonstigeevaporated

Vorschrift

162 mg (0.14 mmol)Pd(PPh3)4 was added under argon at room temperature to a solution of 2.0 g (9.25 mmol) methyl-6-bromo-pyridine-2-carboxylate in 46 ml N,N-dimethylformamide and the mixture was heated to 80° C. Then 4.52 g (13.9 mmol) cesium carbonate and 2.1 g (10.18 mmol) of 4-(trifluoromethoxy)phenylboronic 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 1.23 g (39%) of 6-(4-Trifluoromethoxy-phenyl)-pyridine-2-carboxylic acid methyl ester

Quelle