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A kind of preparation method of 3,3'-bisindole compound

A technology of bisindole compounds and indole derivatives, which is applied in the field of preparation of 3,3'-bisindole compounds, can solve the problems of limited application range of reaction substrates, harsh reaction conditions, expensive use, etc., and achieve high yield High, easy to react, and mild reaction conditions

Inactive Publication Date: 2018-08-03
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above method has the following disadvantages: harsh reaction conditions, use of expensive metal catalysts, limited scope of application of the reaction substrate and generation of symmetrically structured products, which are difficult to separate.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Will N -Acetyl-3-indolinone 1.75 g (10 mmol), 1,2-dimethylindole 1.35 g (10 mmol) and cuprous iodide 0.19 g (1.0 mmol) were dissolved in ethanol and heated to 60 degrees Celsius , after reacting for 12 hours, extracted with dichloromethane, combined the organic layers, dried over anhydrous sodium sulfate, and recrystallized using dichloromethane / methanol to obtain a white solid product N -Acetyl-3-( N -Methylindole-3)-indole (2.8 g, 92% yield), mp 175-177°C.

[0036] 1 (400 MHz, Chloroform- d ) δ: 8.57 (d, J = 8.1 Hz, 1H), 7.53 (dt, J =7.9, 1.0 Hz, 1H), 7.49 (dt, J = 7.8, 1.0 Hz, 1H), 7.46 (d, J = 3.3 Hz, 1H),7.45 – 7.41 (m, 1H), 7.39 (dt, J = 8.3, 0.9 Hz, 1H), 7.33-7.29 (m, 1H), 7.28- 7.23 (m, 1H), 7.13 (m J = 8.0, 6.9, 1.0 Hz, 1H), 3.82 (s, 3H), 2.71 (s, 3H), 2.50 (s, 3H);

[0037] 13 C NMR (101MHz, Chloroform- d ) δ: 168.5, 136.9, 136.0, 134.7, 131.0 ,127.7 , 125.2 , 123.5 , 123.1, 121.2, 120.9, 119.6, 119.1, 116.7, 108.8, 25.8, 14.1.1, 1

[0038] H...

Embodiment 2

[0040] Will N - Acetyl-3-indolinone 1.75 g (10 mmol), N - Ethyl indole 1.35g (10 mmol) and iodine 2.53g (10 mmol) were dissolved in ethanol, heated to 80 degrees Celsius, after 24 hours of reaction, extracted with dichloromethane, combined organic layers, dried over anhydrous sodium sulfate, distilled water Chloromethane / methanol recrystallization gave 2.89 g of white solid product N-acetyl-3-(N-ethylindole-3)-indole, with a yield of 95%. mp 145-147°C.

[0041] 1 (400 MHz, Chloroform- d ) δ: 8.57 (d, J= 8.2 Hz, 1H), 7.78 (dt, J =7.8, 1.0 Hz, 1H), 7.60 (s, 1H), 7.45 (m, J = 8.4, 7.2, 1.3 Hz, 1H), 7.38 -7.30 (m, 3H), 7.25 (d, J = 2.4 Hz, 1H), 7.01 (dd, J = 8.9, 2.4 Hz, 1H), 3.87(d, J = 1.6 Hz, 6H), 2.72 (s, 3H);

[0042] 13 C NMR (101 MHz, Chloroform- d ) δ: 168.5, 136.3, 136.1, 130.1, 127.0, 125.5, 125.4, 123.7, 122.2, 121.2, 120.3 , 120.1, 119.8, 116.8, 109.7, 107.5, 41.2, 14.2

[0043] HRMS (ESI): m / z [M+H] + calcd. for C 20 h 18 N 2 O: 303.1492, found: ...

Embodiment 3

[0045] Will N - Acetyl-3-indolinone 1.75g ​​(10 mmol), N- 2.07 g (10 mmol) of benzyl indole and 1.62 g (10 mmol) of ferric chloride were dissolved in 1,2-ethylene glycol, heated to 140 degrees Celsius, and after 10 hours of reaction, extracted with dichloromethane, and the organic layers were combined. Dry over anhydrous sodium sulfate and recrystallize from dichloromethane / methanol to give the product as a white solid N -Acetyl-3-( N -benzylindole-3)-indole 3.1 g, yield 85%. mp 130-132°C.

[0046] 1 H NMR (400 MHz, Chloroform- d ) δ: 8.59 (d, J = 8.3 Hz, 1H), 7.87 (d, J = 7.8 Hz, 1H), 7.80 (d, J = 7.8 Hz, 1H), 7.68 (s, 1H), 7.52 – 7.29 (m, 8H),7.27 (d, J = 1.2 Hz, 1H), 7.26-7.20 (m, 2H), 5.43 (s, 2H), 2.72 (s, 3H);

[0047] 13 C NMR (101 MHz, Chloroform- d ) δ: 168.5, 137.2, 136.9, 136.1, 128.9, 127.8, 126.9, 126.7, 125.5, 123.7, 122.6, 121.4, 120.3, 120.1, 117.1, 116.8, 110.31, 208.2

[0048] HRMS (ESI): m / z [M+H] + calcd. for C 25 h 20 N 2 O: 365,1648, ...

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Abstract

The invention provides a preparation method of 3,3'-bisindole compounds. The preparation method comprises the following steps: adding 3-indolone derivatives, indole derivatives and a catalyst into a solvent, reacting and purifying. The reaction general formula of the preparation method is disclosed in the specification. The preparation method provided by the invention has the advantages of accessible raw materials, mild reaction conditions, simple synthesis steps, easy operation, easy separation and purification of the synthetic product, high yield of the target product, and easy amplification for reaction, and thus, has wide application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and more specifically relates to a preparation method of a 3,3'-bisindole compound. Background technique [0002] Bisindole derivatives are common structures in natural products and medicines, and the construction methods of bisindole often have high practical value. Bisindole compounds and their derivatives are a class of natural products that widely exist in terrestrial and marine organisms. They often have a wide range of medicinal activities, such as regulating the metabolism of estrogen, and have good inhibitory activity on the growth of cancer cells. For example, bis-indolemethyl compounds can induce apoptosis of cancer cells without affecting normal cells, and their antibacterial activity can relieve neuromuscular pain. In addition, bisindole compounds are also key intermediates for the synthesis of various heterocyclic molecules and complex alkaloids. In addition, bisindole de...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 翁江鲁桂郭靖
Owner SUN YAT SEN UNIV
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