Synthesis method of 3-amino-5-bromoquinoline

A synthesis method and technology of bromoquinoline, applied in directions such as organic chemistry, can solve problems such as increasing drug activity, and achieve the effects of simple raw materials, reasonable process selection, and simple synthesis route.

Active Publication Date: 2021-02-19
SUZHOU KANGRUN PHARMA
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  • Abstract
  • Description
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Problems solved by technology

At present, there is no known therapeutic drug that can effectively inhibit the occurrence of liver cancer. Therefore, the use of PI5P4K is expected to become a potential target for the treatment of cancer and other diseases, and the modification of 3-amino-5-bromoquinoline is expected to increase its drug activity (WO2019126731A )

Method used

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  • Synthesis method of 3-amino-5-bromoquinoline

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Embodiment Construction

[0024] The present invention will be further described below in conjunction with specific examples, but the examples are only exemplary and do not constitute any limitation to the scope of the present invention. Those skilled in the art should understand that the details and forms of the technical solutions of the present invention can be modified or replaced without departing from the spirit and scope of the present invention, but these modifications and replacements all fall within the protection scope of the present invention.

[0025] The synthetic technique of 3-amino-5-bromoquinoline of the present invention is to be raw material with 5-bromoquinoline, obtains 5-bromo-3-iodoquinoline with TBHP and iodine through non-metallic catalytic oxidation reaction, and NH 2 Boc carries out palladium-catalyzed coupling and hydrolysis to obtain 3-amino-5-bromoquinoline, and the reaction formula is as follows:

[0026] .

[0027] The specific synthesis steps are as follows:

[002...

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Abstract

The invention discloses a synthesis method of 3-amino-5-bromoquinoline, which comprises the following steps of: by using 5-bromoquinoline as a raw material, carrying out non-metal catalytic oxidationreaction on the 5-bromoquinoline, TBHP and iodine to obtain 5-bromo-3-iodoquinoline, and carrying out palladium catalytic coupling and hydrolysis on the 5-bromo-3-iodoquinoline and NH2Boc to obtain the 3-amino-5-bromoquinoline. The synthesis method is simple in synthesis route, reasonable in process selection, low in raw material cost, simple and easily available in raw materials, convenient in operation and post-treatment, high in total yield, free of highly toxic reagents, easy in amplification and capable of realizing large-scale production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and in particular relates to a synthesis method of 3-amino-5-bromoquinoline. Background technique [0002] 3-Amino-5-bromoquinoline is an important medicinal chemical intermediate. Due to the unique structure of quinoline, it is often used as a modification group to introduce various candidate drugs to improve the biological activity of the original compound. In 2019, Johan LINDSTRÖM et al. invented an aminopyridine derivative as a phosphatidylinositol-5-phosphate-4-kinase inhibitor (PI5PK4 inhibitor) for the treatment of cancer, neurodegenerative diseases, inflammatory diseases and metabolic disease. Among them, 3-amino-5-bromoquinoline and aminopyridine were docked into this series of compounds, and it was found that the introduction of 3-amino-5-bromoquinoline enhanced the curative effect of the original compound. At present, there is no known therapeutic dr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38
CPCC07D215/38
Inventor 赵丽芳徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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