Reacción #821972

Ecuación de reacción

sodium bicarbonate

2-[4-(5-bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol

4-chlorophenylboric acid

4-chlorophenylboric acid

→

2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 12 hours
2. 2
   Temperaturathe mixture was refluxed for 8 hours
3. 3
   OtroThe reaction mixture was evaporated down in vacuo
4. 4
   FiltraciónThe precipitate was filtered off
5. 5
   Lavadowashed with diethyl ether
6. 6
   Otrodried in vacuo

Procedimiento

40 mL of 2 N aqueous sodium bicarbonate solution was added to a suspension of 13.20 g (39.74 mmol) of 2-[4-(5-bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol, 9.32 g (59.60 mmol) of 4-chlorophenylboric acid, and 2.30 g (1.99 mmol) of tetrakis(triphenylphosphane)palladium in 400 mL of 1,4-dioxane and the mixture was refluxed for 12 hours. Another 4.66 g of 4-chlorophenylboric acid and 1.14 g of tetrakis(triphenylphosphane)palladium were added and the mixture was refluxed for 8 hours. The reaction mixture was evaporated down in vacuo and the residue was stirred with EtOAc and water. The precipitate was filtered off, washed with diethyl ether, and dried in vacuo. Yield: 10.70 g (74% of theoretical); C22H18ClNO2 (M=363.837); calc.: molpeak (M+H)+: 364/366 (Cl); found: molpeak (M+H)+: 364/366 (Cl); Rf value: 0.47 (silica gel, DCM/EtOAc 2:1).

Fuente