反応 #45584

反応方程式

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

収率 75.8%

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

収率 75.8%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度After cooling
2. 2
   その他the reaction liquid
3. 3
   濃縮was concentrated under reduced pressure
4. 4
   その他the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1→8:1→5:1)

実験手順

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.

出典