Reacción #45583

Ecuación de reacción

(2-bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide 4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate

p-toluenesulfonic acid monohydrate

toluene

→

compound

Rendimiento 85.7%

7-Bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Rendimiento 85.7%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux for 1.5 hours
3. 3
   TemperaturaAfter cooling
4. 4
   Otrothe reaction liquid
5. 5
   Lavadosuccessively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
6. 6
   Secadodried on anhydrous magnesium sulfate
7. 7
   Otrothe solvent was evaporated away under reduced pressure
8. 8
   Otroto obtain a pale brown residue
9. 9
   OtroThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Procedimiento

Next, a mixture of (2-bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide/4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate mixture (160 mg, 0.426 mmol), p-toluenesulfonic acid monohydrate (24 mg, 0.128 mmol) and toluene (13 ml) was heated under reflux for 1.5 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (129 mg) as a colorless solid.

Fuente