5-フルオロインドール 化学特性,用途語,生産方法
外観
白色～うすい褐色、結晶～結晶性粉末
用途
有機合成原料。
化学的特性
off-white crystalline powder
使用
5-Fluoroindole is a reactant used in various syntheses. It was used in the synthesis of Spirotetrahydro β-Carbolines (Spiroindolones), which is a new class of potent and orally efficacious compounds for the treatment of malaria. 5-Fluoroindole was also a reactant in direct indole and pyrrole couplings to carbonyl compound in total synthesis of Acremoauxin A and Oxazinin 3.
製造方法
5-Fluoroindole is prepared from 2-(5-fluoro-2-nitrophenyl)-5-acetonitrile.
10% Pd/C (110 mg) was transferred into a round-bottom flask under a nitrogen atmosphere, followed by the addition of 2-(5-fluoro-2-nitrophenyl)-5-acetonitrile (564 mg, 3.13 mmol) in anhydrous ethanol (25 mL). The mixture was degassed and backfilled with hydrogen gas for a total of three cycles, then stirred overnight. After replacing the hydrogen with nitrogen, a second portion of 10% Pd/C (110 mg) was added to the reaction mixture, and hydrogen gas was reintroduced. The completion of the reaction was monitored by ¹⁹F NMR. Subsequently, the hydrogen gas was replaced with nitrogen, and chloroform (CHCl₃) was added to quench the unreacted Pd/C. The reaction mixture was concentrated under reduced pressure, then partitioned between dichloromethane (DCM) and water. After separation, the aqueous phase was back-extracted, and the combined organic layers were washed with brine, dried over Na₂SO₄, and concentrated under reduced pressure. Column chromatography (mobile phase: DCM) afforded 5-fluoroindole as a white solid.
Yield: 342 mg, 2.53 mmol (81% yield based on 2-(5-fluoro-2-nitrophenyl)-5-acetonitrile).
¹H NMR (400 MHz, CDCl₃) δ: 7.27 (m, 3H), 6.96 (t, 1H), 6.53 (t, 1H).
¹⁹F NMR (376 MHz, CDCl₃) δ: –100.22.
定義
ChEBI: 5-fluoroindole is an organofluorine compound that is the 5-fluoro derivative of indole.
5-フルオロインドール 上流と下流の製品情報
原材料
準備製品