반응 #45873

반응 방정식

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

2-(tri-n-butylstannyl)thiophene

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

→

compound

수율 96.0%

2-Cyclopropyl-7-fluoro-5-methyl-6-(thiophen-2-yl)-1,3-benzoxazole-4-carbonitrile

수율 96.0%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   기타the insoluble matter was separated by filtration
3. 3
   세척with washing with ethyl acetate
4. 4
   세척The filtrate was washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타The insoluble matter was separated by filtration
7. 7
   기타the solvent was evaporated away
8. 8
   기타the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

실험 절차

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-77) (200 mg, 0.68 mmol), 2-(tri-n-butylstannyl)thiophene (280 μl, 0.88 mmol) and 2,6-di-tert-butyl-p-cresol (2 grains) were dissolved in 1,4-dioxane (6 ml), and at room temperature, bis(triphenylphosphine)palladium(II) dichloride (48 mg, 0.07 mmol) was added. The solution was stirred under nitrogen atmosphere at 100° C. for 15 hours. After cooling to room temperature, the insoluble matter was separated by filtration with washing with ethyl acetate. The filtrate was washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=19:1, v/v) to obtain the entitled compound (194 mg, 96%) as a white solid.

출처