Reacción #45717

Ecuación de reacción

tributyl(1-ethoxyvinyl)tin

6-Bromo-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

→

solid

Rendimiento 66.0%

6-(1-Ethoxyvinyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Rendimiento 66.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby heating
2. 2
   Temperaturaunder reflux for 3 days
3. 3
   OtroThe insoluble matter was removed by filtration through Celite
4. 4
   Lavadoby washing with ethyl acetate
5. 5
   OtroThe solvent was evaporated away under reduced pressure
6. 6
   Otrothe resulting residue was purified by silica gel column chromatography (dichloromethane:hexane=1:2 to 2:3 to 9:1 to dichloromethane:methanol=200:1)

Procedimiento

6-Bromo-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-168) (0.80 g, 2.68 mmol) was dissolved in toluene (25 ml), then tributyl(1-ethoxyvinyl)tin (1.30 ml, 3.85 mmol), 2,6-di-tert-butylcresol (12 mg, 0.05 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.10 g, 0.14 mmol) were added followed by heating under reflux for 3 days. The insoluble matter was removed by filtration through Celite, followed by washing with ethyl acetate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:hexane=1:2 to 2:3 to 9:1 to dichloromethane:methanol=200:1) to obtain a brown solid (0.51 g, 66%).

Fuente