反応 #45903

反応方程式

2,6-di-tert-butyl-paracresol

7-Bromo-4-cyano-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

tert-butyl methyl-(3-tri-n-butylstannylcyclopent-2-enyl)carbamate

→

compound

収率 88.0%

tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate

収率 88.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度cooled to room temperature
2. 2
   その他The insoluble matter was separated by filtration
3. 3
   洗浄with washing with ethyl acetate
4. 4
   濃縮The filtrate was concentrated under reduced pressure
5. 5
   その他The solvent was evaporated away
6. 6
   その他the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

実験手順

7-Bromo-4-cyano-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-339) (275 mg, 0.72 mmol) and tert-butyl methyl-(3-tri-n-butylstannylcyclopent-2-enyl)carbamate (I-332) (453 mg, 0.93 mol) were dissolved in 1,4-dioxane (8 ml), and at room temperature, 2,6-di-tert-butyl-paracresol (3 mg, 0.01 mmol) and then bis(triphenylphosphine)palladium(II) dichloride (50 mg, 0.07 mmol) were added. The solution was stirred under nitrogen atmosphere at 100° C. for 24 hours, then cooled to room temperature. The insoluble matter was separated by filtration with washing with ethyl acetate. The filtrate was concentrated under reduced pressure. The solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (316 mg, 88%) as a colorless gel.

出典