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Method for preparing unsymmetrical bis(indolyl)methane compound

A compound and alkyl technology, applied in the field of preparation of asymmetric bis-indolylmethane compounds, to achieve good applicability, simple reaction system, and good anti-senile dementia effects

Inactive Publication Date: 2011-08-10
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the reported methods for the synthesis of bis-indolylmethane derivatives, most of them focus on symmetrical bis-indolylmethane compounds, while there are fewer synthetic methods for asymmetric bis-indolylmethane compounds, based on bis-indolylmethane The important use of indole methane compounds, the development and synthesis of asymmetric indole-substituted bis-indole methane compounds has important significance

Method used

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  • Method for preparing unsymmetrical bis(indolyl)methane compound
  • Method for preparing unsymmetrical bis(indolyl)methane compound
  • Method for preparing unsymmetrical bis(indolyl)methane compound

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Embodiment 1

[0017] Synthesis of 3a

[0018] Add 0.5 to 500 mL of water to a dry 1 to 1000 milliliter (ml) reaction bottle, add 0.01 to 10 mmol InX 3 , 0.2~200mmol of substrate 1a and 0.3~300mmol of substrate 2a, stirred and reacted at a certain temperature for 5 hours, extracted the aqueous phase with ethyl acetate, dried the organic phase with anhydrous sodium sulfate, concentrated, and purified by flash silica gel column chromatography to obtain the product 3a .

[0019]

[0020] white solid; 1 H NMR (400MHz, Acetone-d 6 .): δ9.90(s, 1H), 9.79(s, 1H), 7.91(d, J=8.4Hz, 1H), 7.32-7.40(m, 4H), 7.22-7.28(m, 2H), 7.19 (s, 1H), 7.16(s, 1H), 7.05(t, J=7.2Hz, 7.2Hz, 1H), 6.89(t, J=7.2Hz, 7.2Hz, 2H), 6.67(s, 1H), 6.62(s, 1H), 2.25(s, 3H); 13 C NMR (125MHz, Acetone-d 6 .): δ169.8, 146.7, 140.0, 136.5, 136.3, 131.9, 131.6, 131.0, 130.9, 128.5, 128.2, 128.0, 126.6, 125.0, 124.8, 124.7, 123.8, 122.1, 121.4, 120.4, 120.0, 1 , 35.9, 21.7; EI-HRMS m / z calculated value C 25 h 2 0N 2 o 2 : ...

Embodiment 2

[0022] Synthesis of 3b

[0023] Operation is with embodiment 1.

[0024]

[0025] white solid; 1 H NMR (400MHz, Acetone-d 6 .): δ11.23(s, 1H), 9.93(s, 1H), 9.79(s, 1H), 7.87-7.91(m, 1H), 7.42-7.53(m, 1H), 7.35-7.38(m, 2H), 7.19-7.29(m, 3H), 7.11(s, 1H), 7.06(t, J=8.4Hz, 7.2Hz, 1H), 6.85-6.91(m, 2H), 6.69-6.74(m, 3H ), 3.60(s, 3H); 13 C NMR (100MHz, Acetone-d 6 .): δ 169.2, 153.6, 145.8, 137.3, 132.4, 131.1, 130.8, 130.1, 129.9, 127.8, 127.4, 125.8, 124.7, 124.0, 121.3, 119.7, 118.9, 118.8, 116.7, 1113.9, 1 , 54.3, 35.1

Embodiment 3

[0027] Synthesis of 3c

[0028] Operation is with embodiment 1.

[0029]

[0030] white solid; 1 H NMR (400MHz, Acetone-d 6 .): δ11.22(s, 1H), 9.93(s, 1H), 9.81(s, 1H), 7.90(d, J=7.2Hz, 1H), 7.36-7.43(m, 6H), 7.24-7.31 (m, 6H), 7.11(s, 1H), 7.01-7.05(m, 2H), 6.89(t, J=8.0Hz, 7.2Hz, 1H), 6.80(d, J=8.8Hz, 1H), 6.72 (s, 1H), 4.91(s, 2H); 13 C NMR (100MHz, Acetone-d 6 .): δ169.5, 152.7, 145.8, 138.2, 137.3, 132.5, 131.1, 130.7, 130.1, 128.3, 127.7, 127.5, 127.4, 127.3, 125.8, 124.7, 124.0, 121.3, 119.6, 18.8, 119.5, , 112.0, 111.9, 111.3, 103.2, 70.2, 35.2

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Abstract

The present invention relates to a method for preparing unsymmetrical bis-indolyl substituted methane compound. The method is realized by using Friedel-Crafts reaction catalyzed by InX3. The method has the advantages of moderate reaction condition, easy and simple operation, good substrate adaptability with water as dissolvant, friendly environment, convenient separation and purification, application prospect for synthesizing unsymmetrical bis(indolyl)methane compound in a large scale.

Description

technical field [0001] The invention relates to a method for preparing unsymmetrical bis-indolylmethane compounds. Background technique [0002] Indole compounds widely exist in nature, and many indole derivatives have certain physiological and pharmacological activities. Among them, bis-indolylmethane and its derivatives, as metabolites of terrestrial and marine organisms, have a wide range of important physiological activities such as anti-tumor, anti-virus, anti-bacterial and anti-inflammatory, and have always been a hot spot in organic chemists and drug research. [0003] Bis-indolylmethane compounds are usually synthesized from aldehydes or ketones and indole in the presence of catalysts. The currently reported catalysts include montmorillonite K-10, LiClO 4 , In(OTf) 3 , I 2 and Michaelis acid etc. Bis-indolylmethane derivatives can be synthesized in good yields using these catalysts. However, in the reported methods for the synthesis of bis-indolylmethane derivat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/18C07D405/14A61K31/405A61P25/28
Inventor 林国强孙兴文林华沈少春臧杨
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI