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A kind of method that nitrile directly synthesizes indole

A direct, indole technology, applied in the field of nitrile synthesis of indole compounds, achieves the effects of high yield, mild conditions and simple operation

Active Publication Date: 2020-08-14
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the disadvantage of this method is that indole must be substituted at the 7-position to react

Method used

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  • A kind of method that nitrile directly synthesizes indole
  • A kind of method that nitrile directly synthesizes indole
  • A kind of method that nitrile directly synthesizes indole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Embodiment 1: the synthesis of 2-phenylindole

[0010]

[0011] Add 0.02 equivalents of anhydrous copper sulfate and 4.0 equivalents of potassium tert-butoxide into a 25 mL Schlenk reaction tube, dry in vacuum for 15 minutes, add 1.5 mL of n-octane and 1 mL of tert-butanol successively under an argon (or nitrogen) atmosphere, and add benzene Nitrile 5.0 equivalents, 2-iodotoluene 2mmol, put a polytetrafluoro stopper on the reaction tube, put it in an oil bath, and react at 90°C for 15h. After the reaction was completed, the solvent was removed by filtration and concentration, separated by column chromatography, and the eluent was petroleum ether / dichloromethane /

[0012] Ethyl acetate (v:v:v=20:10:1) gave a white solid, 2-phenylindole; the yield was 81%.

[0013] The white solid was analyzed to be 2-phenylindole by chemical shift and splitting of proton nuclear magnetic resonance (1H NMR) and carbon nuclear magnetic resonance (13C NMR).

[0014] 1 H NMR (400MHz, C...

Embodiment 2

[0015] Embodiment 2: Synthesis of 5-bromo-2-phenylindole

[0016]

[0017] Add 0.02 equivalents of anhydrous copper sulfate and 4.0 equivalents of potassium tert-butoxide into a 25 mL Schlenk reaction tube, dry in vacuum for 15 minutes, add 1.5 mL of n-octane and 1 mL of tert-butanol, 5.0 equivalents of benzonitrile, and 5 -Bromo-2-iodotoluene 2mmol, put a polytetrafluoro stopper on the reaction tube, put it in an oil bath, and react at 60°C for 27h. After the reaction was completed, the solvent was removed by filtration and concentration, separated by column chromatography, and the eluent was petroleum ether / dichloromethane / ethyl acetate (v:v:v=20:10:1) to obtain 5-bromo-2-benzene Kelindole white solid; yield 84%.

[0018] 1 H NMR (400MHz, CDCl 3 )δ8.34(s,1H),7.74(s,1H),7.63(d,J=7.2Hz,2H),7.44(t,J=7.2Hz,2H),7.34(t,J=7.2Hz, 1H), 7.26(s, 2H), 6.75(s, 1H). 13 C NMR (100MHz, CDCl 3 )δ139.1, 135.4, 131.8, 131.0, 129.1, 128.2, 125.3, 125.1, 123.1, 113.4, 112.3, 99.4.

Embodiment 3

[0019] Example 3: Synthesis of 5-chloro-2-phenylindole

[0020]

[0021] Add 0.02 equivalents of anhydrous copper sulfate and 4.0 equivalents of potassium tert-butoxide into a 25 mL Schlenk reaction tube, dry in vacuum for 15 minutes, add 1.5 mL of n-octane and 1 mL of tert-butanol, 5.0 equivalents of benzonitrile, and 5 - 2 mmol of chloro-2-iodotoluene, put a polytetrafluoro stopper on the reaction tube, put it into an oil bath, and react at 90°C for 12h. After the reaction was completed, the solvent was removed by filtration and concentration, separated by column chromatography, and the eluent was petroleum ether / dichloromethane / ethyl acetate (v:v:v=20:10:1) to obtain 5-chloro-2-benzene Kelindole white solid; yield 84%.

[0022] 1 H NMR (400MHz, CDCl 3 )δ8.32(s,1H),7.64-7.62(m,2H),7.58(t,J=2.0Hz,1H),7.044(t,J=7.6Hz,2H),7.34(tt,J=7.2 ,1.2Hz,1H),7.29(d,J=8.8Hz,1H),7.13(dd,J=8.4,2.0Hz,1H),6.75(dd,J=2.4,0.8Hz,1H). 13 C NMR (100MHz, CDCl 3 )δ139.3, 135.1, 131.9, 130.3, 1...

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Abstract

The invention discloses a method for directly synthesizing indole by using nitrile. The method is characterized in that a 2-iodotoluene derivative is served as a substrate, anhydrous copper sulfate, potassium tert-butoxide, a cyanophenyl derivative and the 2-iodophene derivative are mixed according to the molar ratio of (0.02-0.1): (2-4): (5-20):1, reaction is carried out for 4-48 hours at 60-105DEG C in a solvent, petroleum ether / dichloromethane / ethyl acetate are mixed according to the volume ratio of (20-5):10:1 so as to be served as an eluent, and separation is carried out by using a silica gel column so as to obtain a target product. The method has the advantages that the operation is simple, the conditions are mild, the yield is high, and the method is a green and novel synthetic method.

Description

technical field [0001] The invention belongs to the technical field of synthesizing indole compounds from nitriles, and in particular relates to a method for directly synthesizing indole with an aryl side chain C-H bond. Background technique [0002] There are many synthetic methods for indole, and the classic method is the Fischer indole synthesis method (Fischer, E., Jourdan, F. Ber. Dtsch. Chem. Ges. 1883, 16, 2241). Most of the indole synthesis methods use aniline and its derivatives as raw materials to synthesize indole and nitro compounds as raw materials to synthesize indole, and the Bartoli indole synthesis method is one example (Bartoli, G.; Palmieri, G.; Bosco, M.; Dalpozz, R. Tetrahedron Lett. 1989, 30, 212). However, the disadvantage of this method is that indole must be substituted at the 7-position to react. Contents of the invention [0003] The purpose of the invention is to propose a method for directly synthesizing indole from nitriles. Anhydrous copper...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C07D471/04C07D209/36C07D209/30C07D401/04
CPCC07D209/08C07D209/30C07D209/36C07D401/04C07D471/04
Inventor 康彦彪单祥欢
Owner UNIV OF SCI & TECH OF CHINA