Réaction #45584

Équation de réaction

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

1-(N-tert-butoxycarbonylamino)-3-tri-n-butylstannyl-2-cyclopentene

2,6-di-tert-butyl-p-cresol

→

compound

Rendement 75.8%

tert-Butyl [3-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)cyclopent-2-enyl]carbamate

Rendement 75.8%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling
2. 2
   Autrethe reaction liquid
3. 3
   Concentrationwas concentrated under reduced pressure
4. 4
   Autrethe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1→8:1→5:1)

Mode opératoire

A 1,4-dioxane (6 ml) solution of 7-bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-46) (89 mg, 0.252 mmol), 1-(N-tert-butoxycarbonylamino)-3-tri-n-butylstannyl-2-cyclopentene (143 mg, 0.302 mmol), bis(triphenylphosphine)palladium(II) chloride (8.8 mg, 0.0126 mmol), 2,6-di-tert-butyl-p-cresol (5.6 mg, 0.0252 mmol) was refluxed overnight. After cooling, the reaction liquid was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1→8:1→5:1) to obtain the entitled compound (87 mg, 75%) as a pale brown solid.

Source