反応 #45873

反応方程式

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

収率 96.0%

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

収率 96.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度After cooling 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
   洗浄The filtrate was washed with saturated brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   その他The insoluble matter was separated by filtration
7. 7
   その他the solvent was evaporated away
8. 8
   その他the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

実験手順

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.

出典