5-Fluoroindole synthesis
- Product Name:5-Fluoroindole
- CAS Number:399-52-0
- Molecular formula:C8H6FN
- Molecular Weight:135.14
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 1?F NMR. Subsequently, the hydrogen gas was replaced with nitrogen, and chloroform (CHCl?) 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 Na?SO?, 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, CDCl?) δ: 7.27 (m, 3H), 6.96 (t, 1H), 6.53 (t, 1H).
1?F NMR (376 MHz, CDCl?) δ: –100.22.
56341-41-4
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Yield:399-52-0 92%
Reaction Conditions:
with bis(trimethylsilyl)amide yttrium(III);4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane in toluene at 120; for 36 h;Inert atmosphere;
Steps:
2 Example 3
Under nitrogen protection, 0.5 mmol of raw 5-fluoro-2-indolinone, 1.2 mmol of pinacol borane and catalyst Y [N(SiMe3) 2] 30.05 mmol, 3 mL of toluene, reacted at 120 C for 36 h, and the product isolation yield was 92%.
References:
Wenzhou Medical University;Zhang Junfang;Cai Wenxuan CN110818608, 2020, A Location in patent:Paragraph 0043-0047
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![5-fluoro-1-[(2-nitrophenyl)methyl]-1H-indole](/CAS/GIF/261762-12-3.gif)
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