Fluoroisoquinolone compound and synthesis method thereof

A technology of isoquinolinone and synthesis method, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalyst, chemical/physical process, etc., can solve the requirements of high reaction conditions, harsh environmental conditions, The problem of high production cost, to achieve the effect of broad industrial prospects, high production efficiency and easy operation

Inactive Publication Date: 2016-08-17
叶芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Wherein, the required environmental conditions in the reaction process of the first preparation method are relatively harsh, generally require higher reaction temperature, and the catalyst is a relatively expensive transition metal in the reaction process, and the production cost is high; the reaction conditions of the second preparation method The same requirements are high, and because it is a multi-step reaction, the yield is limited
Therefore, it is still a challenge to find a synthetic method of fluorine-substituted isoquinolinones with mild reaction conditions and high yields.

Method used

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  • Fluoroisoquinolone compound and synthesis method thereof
  • Fluoroisoquinolone compound and synthesis method thereof
  • Fluoroisoquinolone compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Dissolve 100 mmol of compound I in the above formula in ether, add 150 mmol of fluorinating agent and 7 mmol of catalyst, raise the temperature to 40°C, stir at a speed of 70 rpm, and continue the reaction for 8 hours. After washing with water for 3 times, adding n-hexane for extraction, drying and concentrating, passing through a silica gel chromatography column, and washing with an equal volume ratio of acetone-n-hexane mixture, the compound II in the above formula was obtained.

[0027] The purity of the target product is 89.3%, and the yield is 93.7%.

Embodiment 2

[0029]

[0030] Dissolve 100 mmol of compound I in the above formula in ether, add 160 mmol of fluorinating agent and 8 mmol of catalyst, raise the temperature to 50°C, stir at a speed of 60 rpm, and continue the reaction for 8 hours. After washing with water for 3 times, adding n-hexane for extraction, drying and concentrating, passing through a silica gel chromatography column, and washing with an equal volume ratio of acetone-n-hexane mixture, the compound II in the above formula was obtained.

[0031] The purity of the target product is 89.8%, and the yield is 94.2%.

Embodiment 3

[0033]

[0034] Dissolve 100 mmol of compound I in the above formula in ether, add 170 mmol of fluorinating agent and 9 mmol of catalyst, raise the temperature to 60°C, stir at a speed of 50 rpm, and continue the reaction for 8 hours. After washing with water for 3 times, adding n-hexane for extraction, drying and concentrating, passing through a silica gel chromatography column, and washing with an equal volume ratio of acetone-n-hexane mixture, the compound II in the above formula was obtained.

[0035] Wherein the purity of the target product is 92.1%, and the yield is 95.2%.

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Abstract

The invention discloses a fluoroisoquinolone compound and a preparation method thereof. The reaction mechanism of the method is characterized in that a compound I reacts with a fluorating agent under the catalysis of a catalyst to generate a ring closing effect in order to generate the compound II, and R in the formulas of the compound I and the compound II is a C1-C6 alkyl group, a C1-C6 alkyloxy group, an aryl group or a heteroaryl group. A high-efficiency multi-component catalyst system is adopted, so the selectivity of an intramolecular cyclization reaction is improved, and the yield of the target product is improved. The preparation method has the advantages of simple steps, simple operation, high production efficiency, mild environment conditions needed by the reaction, and wide industrial application values.

Description

Technical field: [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a synthesis method of fluorine-substituted isoquinolinone compounds. Background technique: [0002] Isoquinolinone compounds are important heterocyclic compounds that widely exist in nature. A variety of compounds can be prepared based on the isoquinolinone ring, which generally have biological activity. Isoquinolinones play an important role in biochemistry, medicinal chemistry and agricultural chemistry. In agriculture, isoquinolinone compounds can be used to make high-efficiency insecticides, and in industry, they can be used as color films and dyes. In addition, these compounds also have important pharmacological effects, such as antihypertensive, antithrombotic or Anti-gastric ulcer etc. Therefore, the research on the synthesis method of isoquinolinone compounds has received extensive attention in recent years. [0003] Present stage, the syntheti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/24C07D401/04B01J31/28
CPCC07D217/24B01J31/28B01J2531/0244B01J2531/847C07D401/04
Inventor 叶芳
Owner 叶芳
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