Reacción #45713

Ecuación de reacción

Tributylstannyl-1-methylpyrrole

2,6-di-tert-butylcresol

2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile

→

7-Fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder heat under nitrogen atmosphere for 3 hours
2. 2
   TemperaturaAfter cooling
3. 3
   Otrothe reaction liquid
4. 4
   Filtraciónwas filtered
5. 5
   Otrothe solvent of the filtrate was evaporate away under reduced pressure
6. 6
   Lavadoeluted with a mixed solvent of n-hexane/ethyl acetate (9:1, v/v→5
7. 7
   Otro1, v/v) to obtain a main product
8. 8
   LavadoAfter washing with isopropyl ether
9. 9
   Filtraciónthe entitled compound (50 mg, 22%) was collected by filtration as a pale yellow solid

Procedimiento

Tributylstannyl-1-methylpyrrole (389 mg, 1.05 mmol), bis(triphenylphosphine)palladium(II) dichloride (49 mg, 0.07 mmol), and a catalytic amount of 2,6-di-tert-butylcresol (2 mg) were added to a toluene (20 ml) solution of 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (200 mg, 0.70 mol), followed by stirring under heat under nitrogen atmosphere for 3 hours. After cooling, the reaction liquid was filtered, and the solvent of the filtrate was evaporate away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and eluted with a mixed solvent of n-hexane/ethyl acetate (9:1, v/v→5:1, v/v) to obtain a main product. After washing with isopropyl ether, the entitled compound (50 mg, 22%) was collected by filtration as a pale yellow solid.

Fuente