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Preparation method and application of 2-acyl-3-aminoindole compounds

A compound and acyl technology, which is applied in the field of preparation of 2-acyl-3-aminoindole compounds, can solve the problems of low yield, cumbersome preparation process, and complicated operation, and achieve simple operation, mild reaction conditions, and increased application effect of possibility

Active Publication Date: 2020-08-21
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a simple method for preparing 2-acyl-3-aminoindole compounds in order to overcome the cumbersome preparation process of 2-acyl-3-aminoindole compounds in the prior art, complicated operation and low yield. -Aminoindole compound method and application thereof

Method used

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  • Preparation method and application of 2-acyl-3-aminoindole compounds
  • Preparation method and application of 2-acyl-3-aminoindole compounds
  • Preparation method and application of 2-acyl-3-aminoindole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of 2-acyl-3-aminoindole:

[0048]

[0049] Add acetophenone (0.5mmol), iodine (0.8mmol) and 2mL of DMSO to a 38mL pressure tube, and after the first reaction at 100°C for 45min (the acetophenone completely disappeared), add 2 -Aminobenzonitrile (0.5mmol), NaHS·H 2 O (2.5mmol) was subjected to the second reaction at 100°C. After 4 hours, the reaction liquid was extracted with ethyl acetate, and the organic layer was washed with saturated sodium thiosulfate and saturated brine, dried over anhydrous sodium sulfate, and then decompressed. The solvent was evaporated to obtain a crude product, which was separated and purified by column chromatography with a mixture of petroleum ether and ethyl acetate to obtain a yellow oil with a total yield of 71%.

[0050] The obtained yellow oil is carried out to the proton nuclear magnetic spectrum test, and the obtained proton nuclear magnetic spectrogram result is:

[0051] ( 1 H-NMR (600MHz, CDCl 3 ,ppm):δ7.95(s,1H),7...

Embodiment 2

[0054] Synthesis of (3-amino-1hydro-indol-2-yl)(4-(methylsulfonyl)phenyl)methanone:

[0055]

[0056] The specific steps are: add 4-thiamphenicol acetophenone (0.5mmol), iodine (0.8mmol) and 2mL of DMSO to a 38mL pressure tube, and carry out the first reaction at 100°C for 60min (4-methylsulfone base acetophenone disappears completely), in the reaction liquid, add 2-aminobenzonitrile (0.5mmol), NaHS·H 2 O (2.5mmol) carried out the second reaction at 100°C. After 7 hours, the reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated sodium thiosulfate and saturated brine respectively, dried over anhydrous sodium sulfate, and reduced The crude product was obtained by pressure evaporation to remove the solvent, and the crude product was separated and purified by column chromatography with a mixture of petroleum ether and ethyl acetate to obtain a yellow solid with a total yield of 76%.

[0057] Gained yellow solid is carried out proto...

Embodiment 3

[0062] Synthesis of (3-amino-1hydro-indol-2-yl)(4-bromophenyl)methanone:

[0063]

[0064] The specific steps are: add 4-bromoacetophenone (0.5mmol), iodine (0.8mmol) and 2mL of DMSO to a 38mL pressure tube, and carry out the first reaction at 100°C for 60min (4-bromoacetophenone disappear completely), add 2-aminobenzonitrile (0.5mmol) to the reaction solution, NaHS·H 2 O (2.5mmol) was subjected to the second reaction at 100°C. After 4 hours, the reaction liquid was extracted with ethyl acetate, and the organic layer was washed with saturated sodium thiosulfate and saturated brine, dried over anhydrous sodium sulfate, and then decompressed. The solvent was evaporated to obtain a crude product, which was separated and purified by column chromatography with a mixture of petroleum ether and ethyl acetate to obtain a yellow solid with a total yield of 72%.

[0065] Gained yellow solid is carried out proton nuclear magnetic spectrum test and carbon nuclear magnetic spectrum tes...

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Abstract

The invention relates to the field of 2-acyl-3-amino indole compound synthesis and discloses a method for preparing a 2-acyl-3-amino indole compound with a structure shown as formula (I). According tothe method provided by the invention, simple 'one-pot' reaction is adopted, conditions are mild and operation is simple; the step of intermediate purification in a multistep synthesis method in the prior art is avoided; the application possibility of the method in practical production is increased.

Description

technical field [0001] The invention relates to the field of synthesis of indole compounds, in particular to a preparation method and application of 2-acyl-3-aminoindole compounds. Background technique [0002] Indole compounds are a class of nitrogen-containing heterocyclic compounds with important physiological activities, which widely exist in natural products and drug molecules, and have been widely used in the fields of medicine, pesticides and materials. Studies have shown that glycine receptor antagonists, virus fusion inhibitors, non-nucleoside transcriptase inhibitors and selective estrogen receptor modulators all contain the skeleton of indole structural units. For a long time, scientific researchers have continuously modified the indole skeleton in a variety of ways to explore new target compounds with pharmaceutical value. [0003] Due to the outstanding value of indole compounds, organic and pharmaceutical synthesis workers focus on the synthesis of multi-subst...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/40C07D405/06C07D409/06
CPCC07D209/40C07D405/06C07D409/06
Inventor 耿肖武侠吴彦东吴安心
Owner HUAZHONG NORMAL UNIV
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