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Process for preparing diindolylmethane derivatives

A technology of diindolylmethane and derivatives, applied in the field of indole synthesis, can solve the problems of low yield, strong acid conditions, expensive reagents and the like

Inactive Publication Date: 2006-09-27
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, in the preparation methods that have been reported, there are many experimental processes involving various problems such as strong acid conditions, expensive reagents, low yield, complicated post-treatment and long reaction time.

Method used

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  • Process for preparing diindolylmethane derivatives
  • Process for preparing diindolylmethane derivatives
  • Process for preparing diindolylmethane derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 0.02 moles of indole and 0.01 moles of benzaldehyde were dissolved in 10 milliliters of methanol, then 0.5 millimoles of tetra-n-butylammonium tribromide was added, and the reaction was stirred and reacted at room temperature at 20° C. for 1 hour, and the reaction was terminated, and 20 milliliters of water was added to precipitate the product. After simple filtration and drying, bis(3-indole)phenylmethane was obtained with a yield of 90%.

[0023]

[0024] mp 123~125℃; IR(KBr) 3415, 1631, 1380, 734cm -1 ; 1 H NMR (500MHz, CDCl 3 )δ7.89 (brs, 2H), 7.38 (d, J=8.0Hz, 2H), 7.33-7.35 (m, 4H), 7.19-7.30 (m, 5H), 7.00 (m, 2H), 6.64 (d , J=1.0Hz, 2H), 5.88(s, 1H)ppm; 13 C NMR (125MHz, CDCl 3 )δ144.2, 136.8, 128.9, 128.4, 127.2, 126.3, 123.8, 122.1, 120.1, 119.8, 119.4, 111.2, 40.3ppm; MS m / z 322 (M + ); HRMS(EI)calcd for C 23 h 18 N 2 : 322.1470; Found 322.1473.

Embodiment 2

[0026] 0.02 moles of indole and 0.01 moles of p-methoxybenzaldehyde were dissolved in 10 milliliters of ethanol, then 0.4 millimoles of tetra-n-butylammonium tribromide was added, stirred and reacted at room temperature 25°C for 0.5 hours, the reaction was terminated, and 20 milliliters of water was added , the product was separated out, and bis(3-indolyl)-(4-methoxybenzene)methane was obtained after simple filtration and drying process with a yield of 94%.

[0027] OMe

[0028]

[0029] mp 179-181°C.IR,: 742, 1417, 1454, 1508, 1610, 2924, 3396cm -1 . 1 H NMR (400Hz, CDCl 3 ): 3.76(s, 3H), 5.80(s, 1H), 6.59(d, J=2.4Hz, 2H), 6.78(d, J=8.1Hz, 2H), 6.93(t, 2H), 7.12(t , 2H), 7.20-7.38 (m, 6H), 7.80 (brs, 2H, NH) ppm. 13 C-NMR (100MHz, CDCl 3 ): 39.2, 56.0, 110.8, 113.6, 118.6, 119.4, 121.8, 123.0, 126.4, 136.2ppm. EIMS: m / z (%): 352 (20, M + ), 236(100).

Embodiment 3

[0031] 0.021 moles of 5-methoxyindole and 0.01 moles of p-phenylbenzaldehyde were dissolved in 12 milliliters of methanol, then 0.6 millimoles of tetra-n-butylammonium tribromide was added, and the reaction was stirred at room temperature at 15° C. for 1.5 hours, and the reaction was completed. After adding 25 ml of water, the product was precipitated. After simple filtration and drying, bis(5-methoxy-3-indolyl)-(4-phenylbenzene)methane was obtained with a yield of 92%.

[0032]

[0033] mp 194-196°C; IR(KBr): 3470, 2965, 1270, 770cm -1 ; 1 H NMR (500MHz, CDCl 3 ): 3.72(s, 6H), 5.84(s, 1H), 6.69(d, J=1.7Hz, 2H), 6.86(m, 4H), 7.21-7.61(m, 11H), 7.81(br s, 2H , NH)ppm. 13 C NMR (125MHz, CDCl 3 ): 40.17, 56.10, 102.24, 111.97, 112.13, 119.36, 124.73, 127.15, 127.19, 127.24, 127.73, 128.96, 129.36, 132.11, 139.07, 141.30, 143.35, 14.z IME.8 (%) m + ).Anal.Calcd for C 31 h 26 N 2 o 2 : C, 81.20; H, 5.72; N, 6.11; Found: C, 81.20; H, 5.76; N, 6.14.

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Abstract

The invention discloses a diindolefiredamp derivant preparing method, which comprises the following steps: using carbinol or alcohol for reaction solvent; carrying on electrophilic reaction with indole and aldehyde for 0.1-5 hours catalyzing by tetranbutyl ammonium tribromide; getting high yield of diindolefiredamp derivant, wherein the mole equivalent weight ratio of indole and aldehyde is 1.8-2.2: 1; the dosage of accelerant tetranbutyl ammonium tribromide is 1-10% mole equivalent weight of indole. The invention has mild conditioned response, which is easy for throwing material and after-treatment.

Description

technical field [0001] The invention relates to an indole synthesis method, in particular to a preparation method of a diindolylmethane derivative. Background technique [0002] Indole compounds not only exist widely in nature, but also have many physiological activities. Using indole nuclei as raw materials to synthesize natural products with physiological activities or to derive a large number of compounds for activity screening has always been the core of indole chemistry research. ; Therefore, their research is very extensive and in-depth, especially how to synthesize indole derivatives more efficiently and greenly has received great attention from people. Among various indole derivatives, diindolylmethane is an important class of skeletons in the total synthesis of natural products and the design of drug molecular targets. Therefore, it is of great significance to study diindolylmethane derivatives, and many methods have been reported for the preparation of such compou...

Claims

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Application Information

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IPC IPC(8): C07D209/30C07D209/32C07D209/14C07D405/14
Inventor 林旭锋崔孙良王彦广
Owner ZHEJIANG UNIV
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