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N-substituted indole diketone compound and its preparation method

An indole dione and compound technology, applied in the field of N-substituted indole dione compounds and their preparation, can solve the problems of large limitation of reaction raw materials, difficult to obtain raw materials, expensive reaction reagents, etc., and reach the scope of application of substrates Wide, improve liver cirrhosis ascites, simple operation effect

Inactive Publication Date: 2014-10-01
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In summary, there are many methods for preparing N-substituted indole diketones, but the raw materials of these reactions are not easy to obtain, and need to go through more complicated synthesis steps; the reaction raw materials in some reactions are limited, The reaction yield is low, the reaction reagents are expensive, and the reaction conditions are relatively harsh, etc.

Method used

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  • N-substituted indole diketone compound and its preparation method
  • N-substituted indole diketone compound and its preparation method
  • N-substituted indole diketone compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Preparation of 1-methylindole-2,3-one

[0049] 1-Methylindole-2,3-ketone adopts the following steps: ①Add 11.4 grams of 2-(2-bromophenyl)-N-methylacetamide, 2.7 grams of 1,10 -Phenanthroline, 1.4 grams of cuprous iodide, 34.6 grams of potassium carbonate, 32.2 grams of tetrabutylammonium bromide, 200 milliliters of toluene, heated to 110°C. Track the reaction with thin-layer chromatography until the reaction raw material 2-(2-bromophenyl)-N-methylacetamide disappears; ②After the reaction is completed, filter the system with diatomaceous earth and remove the solvent with a rotary evaporator to obtain Crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5 : 1) to obtain 6.9 g of 1-methylindole-2,3-one with a yield of 85%. Melting point: 126-128°C.

[0050] IR (KBr, cm-1): 2924, 1745, 1607, 1470, 756.

[0051] 1 H NMR (CDCl 3 , 500 MHz): δ 7.62-7.58 (m, 2H), 7.12 (t, J = 7.5 Hz, 1H), 6.89 (d,...

Embodiment 2

[0054] Example 2: Preparation of 1-propylindole-2,3-one

[0055] 1-Propylindole-2,3-ketone adopts the following steps: ①Add 12.8 grams of 2-(2-bromophenyl)-N-propylacetamide, 2.7 grams of 1,10 -Phenanthroline, 0.95 g of cuprous iodide, 13.8 g of potassium carbonate, 80.6 g of tetrabutylammonium bromide, 200 ml of toluene, heated to 110°C. Track the reaction with thin-layer chromatography until the reaction raw material 2-(2-bromophenyl)-N-propylacetamide disappears; ②After the reaction is completed, filter the system with diatomaceous earth and remove the solvent with a rotary evaporator to obtain Crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5 : 1) to obtain 6.9 g of 1-propylindole-2,3-one with a yield of 74%. Melting point: 72-74°C.

[0056] IR (KBr, cm-1): 1743, 1612, 1470, 754.

[0057] 1 H NMR (CDCl 3 , 500 MHz): δ 7.59-7.56 (m, 2H), 7.10 (t, J = 7.5 Hz, 1H), 6.89 (d, J = 8.0 Hz, 1H), 3.68(t...

Embodiment 3

[0060] Example 3: Preparation of 1-butylindole-2,3-one

[0061] 1-Butylindole-2,3-ketone adopts the following steps: ①Add 13.5 grams of 2-(2-bromophenyl)-N-butylacetamide, 1.8 grams of 1,10 -Phenanthroline, 0.95 g of cuprous iodide, 34.6 g of potassium carbonate, 80.6 g of tetrabutylammonium bromide, 200 ml of toluene, heated to 110°C. Use thin-layer chromatography to follow the reaction until the reaction raw material 2-(2-bromophenyl)-N-butylacetamide disappears; ②After the reaction is completed, filter the system with diatomaceous earth and remove the solvent with a rotary evaporator to obtain Crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5 : 1) to obtain 6.2 g of 1-butylindole-2,3-one with a yield of 61%. Melting point: 36-38°C.

[0062] IR (KBr, cm-1): 1733, 1610, 1468, 752.

[0063] 1 H NMR (CDCl 3 , 500 MHz): δ7.58-7.56 (m, 2H), 7.09 (t, J = 7.5 Hz,1H), 6.89 (d, J = 8.0 Hz,1H), 3.70 (t, J...

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Abstract

The invention relates to an N-substituted indole diketone compound and a preparation method thereof. The structural formula of the compound is: wherein: R1 is: OMe or OTs; R2 is:, an alkyl group with one to twelve carbons, isopropyl, cyclopropyl, benzyl, alkyl, phenethyl, hydroxylethyl, furan-2-ylmethyl or naphthalen- 1-yl; R3 is: R3 is: H, -Me, -OMe, -OEt, -Br, -Cl or -COOEt. The N-substituted indole diketone compound is a kind of active skeleton of important drug molecules and an organic synthesis intermediate, and occupies an important position in medicinal chemistry. The raw materials of the method of the invention are easy to obtain, the reaction yield is high, and the substrate has a wide application range. Conventional solvents are used in the reaction, the operation is simple, the conditions are mild, the reaction is environmentally friendly, and the reaction yield can reach up to 85%, which is very suitable for industrial production.

Description

technical field [0001] The invention relates to an N-substituted indole diketone compound and a preparation method thereof. Background technique [0002] Nitrogen-containing heterocycle is a very common pharmacophore in the field of drug research, and it is one of the important targets of small molecule drug development today. In 2007, all of the top 25 branded drugs in the global sales volume had nitrogen-containing heterocyclic skeletons. The antibacterial, anti-tumor and other physiological activities of nitrogen-containing heterocyclic compounds, as well as their significance in basic theory and applied research, make the synthesis of such compounds and the study of their chemical and biological properties an important topic in organic chemistry and related fields. Hot topics. Indoledione is an important class of nitrogen-containing heterocycles, which have been widely used in the field of biomedicine. These compounds have been widely used clinically as an important c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/38
Inventor 许斌孙杰刘秉新
Owner SHANGHAI UNIV