Reacción #963418

Ecuación de reacción

water

N-(5-bromopyridin-3-yl)benzamide

(3,4-dimethylphenyl)boronic acid

potassium carbonate

→

N-[5-(3,4-Dimethylphenyl)pyridin-3-yl]benzenecarboxamide

Disolventes

DMF

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   ConcentraciónThe reaction mixture was concentrated slightly on a rotary evaporator
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Extracciónextracted with dichloromethane
5. 5
   ConcentraciónThe organic phase was concentrated
6. 6
   Otropurified by column chromatography on silica gel (dichloromethane/methanol 100:1→100:4)

Procedimiento

At 50° C., 4.5 g (16.2 mmol) of N-(5-bromopyridin-3-yl)benzamide, 3.0 g (19.5 mmol) of (3,4-dimethylphenyl)boronic acid and 4.5 g (32.5 mmol) of potassium carbonate were dissolved in 59 ml of 1,2-dimethoxyethane, 19 ml of water and 117 ml of DMF. The mixture was flushed with argon, 0.1 g (0.08 mmol) of tetrakis(triphenylphosphine)palladium(0) was added and the mixture was stirred at 85° C. for 12 h. The reaction mixture was concentrated slightly on a rotary evaporator, diluted with water and extracted with dichloromethane. The organic phase was concentrated and purified by column chromatography on silica gel (dichloromethane/methanol 100:1→100:4).

Fuente