Synthesis method of medical intermediate phenanthridone compound

A synthesis method and compound technology, applied in the field of synthesis of phenanthridone compounds, can solve the problems of high cost, complicated operation, environmental pollution, etc., and achieve the effect of good application prospects

Inactive Publication Date: 2017-08-18
周晓芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to overcome the above-mentioned defects such as low yield, environmental pollution, complicated operation and high cost in the synthesis method of phenanthridone compounds i

Method used

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  • Synthesis method of medical intermediate phenanthridone compound
  • Synthesis method of medical intermediate phenanthridone compound
  • Synthesis method of medical intermediate phenanthridone compound

Examples

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Example Embodiment

[0023] Example 1

[0024]

[0025] Under the protection of inert gas, 100ml of mixed organic solvent of acetic acid and acetonitrile with a volume ratio of 2:1 was added to the reactor, and 10mmol of the compound of the above formula (I-1), 12mmol of the compound of the above formula (II-1), 1mmol of catalyst copper triflate, 1mmol of cocatalyst, 20mmol of bis(trifluoroacetic acid) iodobenzene, and then 15mmol of isoamyl nitrite was added to the reaction solution. While stirring, the temperature was raised to 50°C by heating, and the reaction was stirred at this temperature for 8 hours. After the reaction was completed, all volatiles were removed in vacuo, the product was extracted with ethyl acetate, the organic phase was removed from the solvent, and the residue was separated by 300-400 mesh silica gel column chromatography. The elution solvent was petroleum ether and acetic acid in a volume ratio of 4:1. A mixture of ethyl esters can obtain the compound of formula (III-1) wit...

Example Embodiment

[0026] Example 2

[0027]

[0028] Under the protection of inert gas, add 10ml of mixed organic solvent of acetic acid and acetonitrile with a volume ratio of 2:1 to the reactor, and then add 1mmol of compound of formula (I-2) and 1.2mmol of compound of formula (II-2) to it in turn , 0.1mmol catalyst copper trifluoromethanesulfonate, 0.1mmol co-catalyst, 2mmol bis(trifluoroacetic acid) iodobenzene, and then add 1.5mmol isoamyl nitrite to the reaction solution. While stirring, the temperature was raised to 50°C by heating, and the reaction was stirred at this temperature for 8 hours. After the reaction was completed, all volatiles were removed in vacuo, the product was extracted with ethyl acetate, the organic phase was removed from the solvent, and the residue was separated by 300-400 mesh silica gel column chromatography. The elution solvent was petroleum ether and acetic acid in a volume ratio of 4:1. A mixture of ethyl esters can obtain the compound of formula (III-3) with a ...

Example Embodiment

[0029] Example 3

[0030]

[0031] Under the protection of inert gas, add 10ml of mixed organic solvent of acetic acid and acetonitrile with a volume ratio of 2:1 into the reactor, and then add 1mmol of compound of formula (I-3) and 1.2mmol of compound of formula (II-3) to it in turn , 0.12mmol catalyst copper trifluoromethanesulfonate, 0.12mmol co-catalyst, 2mmol bis(trifluoroacetic acid) iodobenzene, and then 1.5mmol isoamyl nitrite was added to the reaction solution. While stirring, the temperature was raised to 50°C by heating, and the reaction was stirred at this temperature for 8 hours. After the reaction was completed, all volatiles were removed in vacuo, the product was extracted with ethyl acetate, the organic phase was removed from the solvent, and the residue was separated by 300-400 mesh silica gel column chromatography. The elution solvent was petroleum ether and acetic acid in a volume ratio of 4:1. A mixture of ethyl esters can obtain the compound of formula (III-...

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Abstract

The invention relates to a synthesis method of a medical intermediate phenanthridone compound. The method comprises the following step of reacting an N-methoxybenzamide compound with an aniline compound in an organic solvent in the presence of a copper catalyst, a cocatalyst, an oxidizing agent and isoamyl nitrite to obtain the phenanthridone compound. According to the method, through unique substrate section and a unique comprehensive reaction system, high-yield synthesis of the phenanthridone compound is achieved and the method has a good application prospect and industrial production potential.

Description

technical field [0001] The present invention relates to a kind of synthetic method of pharmaceutical intermediate, more particularly relate to a kind of synthetic method of the phenanthridone compound as pharmaceutical intermediate. Background technique [0002] Phenanthridone structure exists in various biologically active molecules, and is one of the important skeleton structures of many anti-tumor active compounds and compounds for treating mental diseases. Phenanthridone compounds, as intermediates in drug synthesis, can be expanded and modified through a variety of reactions to obtain biologically active compounds, which play an important role in organic chemical synthesis. [0003] In recent years, more and more attention has been paid to the development of synthetic methods of phenanthridone compounds, and a lot of research has been carried out on it, and some new synthetic routes and methods have been obtained. So far, a variety of synthetic methods related to phena...

Claims

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Application Information

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IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 周晓芳
Owner 周晓芳
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