반응 #45903

반응 방정식

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

수율 88.0%

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

수율 88.0%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   기타The insoluble matter was separated by filtration
3. 3
   세척with washing with ethyl acetate
4. 4
   농축The filtrate was concentrated under reduced pressure
5. 5
   기타The solvent was evaporated away
6. 6
   기타the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

실험 절차

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.

출처