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A kind of preparation method of 1h-pyrazolo[3,4-b]pyridine-3-carbaldehyde

A technology of 4-b and pyrazolo, which is applied in the field of preparation of 1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde, which can solve the problems of harsh reaction conditions, large production sewage discharge and low production efficiency, etc. problems, to achieve the effect of high total yield, high production safety factor and low cost

Active Publication Date: 2021-08-31
ASTATECH CHENGDU BIOPHARM CORP
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The object of the present invention is to overcome the deficiencies in the prior art, such as expensive raw materials and auxiliary materials, use of expensive catalysts, harsh reaction conditions, high synthesis difficulty, low production efficiency or large production sewage discharge, and provide a 1H-pyrazolo[3,4 -b] the preparation method of pyridine-3-carbaldehyde, to at least achieve the effects of low cost, cheap and easy-to-obtain raw materials, simple reaction process, convenient operation, safety, high total yield and environmental friendliness

Method used

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  • A kind of preparation method of 1h-pyrazolo[3,4-b]pyridine-3-carbaldehyde
  • A kind of preparation method of 1h-pyrazolo[3,4-b]pyridine-3-carbaldehyde
  • A kind of preparation method of 1h-pyrazolo[3,4-b]pyridine-3-carbaldehyde

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Embodiment 1

[0029] A preparation method of 1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde, the synthetic route is:

[0030]

[0031] Include the following steps:

[0032] Preparation of S1.1-(2-fluoropyridin-3-yl)-2,2-diethoxyethanone:

[0033] Add 2-fluoropyridine (50g, 0.51mol, 1.0eq) and tetrahydrofuran (500g) into a three-necked flask, and at -60°C to -80°C, add dropwise a ring containing 2.0mol / L lithium diisopropylamide Hexane solution (330.0mL, 0.66mol, 1.3eq), after the dropwise addition, keep the reaction for 1~2h; 134.8g, 0.76mol, 1.5eq), heat preservation reaction for 1~2h, the reaction of the central control raw material has been completed, the reaction is quenched with water, the liquid is separated, and the organic phase is concentrated to obtain 1-(2-fluoropyridin-3-yl)- 2,2-diethoxyethanone (99.5 g, 85% yield).

[0034] Preparation of S2.3-(diethoxymethyl)-1H-pyrazolo[3,4-b]pyridine:

[0035] 1-(2-fluoropyridin-3-yl)-2,2-diethoxyethanone (50g, 0.22mol, 1.0eq) was dissolv...

Embodiment 2

[0041] A preparation method of 1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde, the synthetic route is:

[0042]

[0043] Include the following steps:

[0044] Preparation of S1.1-(2-fluoropyridin-3-yl)-2,2-diethoxyethanone:

[0045]Add 2-fluoropyridine (50g, 0.51mol, 1.0eq) and tetrahydrofuran (500g) into a three-necked flask, and at -60°C to -80°C, dropwise add a ring containing 2.0mol / L lithium diisopropylamide Hexane solution (330mL, 0.66mol, 1.3eq), after the dropwise addition, keep the reaction for 1~2h; then add 2,2-dimethoxyacetic acid methyl ester (101.9 g, 0.76mol, 1.5eq), heat preservation reaction for 1~2h, the reaction of the central control raw material has been completed, the reaction is quenched with water, the liquid is separated, and the organic phase is concentrated to obtain 1-(2-fluoropyridin-3-yl)-2 , 2-dimethoxyethanone (87.4 g, 86% yield).

[0046] Preparation of S2.3-(dimethoxymethyl)-1H-pyrazolo[3,4-b]pyridine:

[0047] 1-(2-fluoropyridin-3-yl)-2,2-d...

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Abstract

The present invention relates to the technical field of organic synthesis, and discloses a preparation method of 1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde, comprising the following steps: S1. making 2-fluoropyridine and 2,2-di Alkoxy acetate reacts under the effect of base to obtain 1-(2-fluoropyridine-3-yl)-2,2-dialkoxyethanone; S2. makes 1-(2-fluoropyridine-3- Base)-2,2-dialkoxyethanone reacts with hydrazine hydrate to obtain 3-(dialkoxymethyl)-1H-pyrazolo[3,4-b]pyridine; S3. makes 3-(two Alkoxymethyl)-1H-pyrazolo[3,4-b]pyridine is hydrolyzed under acidic conditions to obtain 1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde; the method has easy raw materials It has the advantages of low cost, convenient process operation, safety, high total yield, no need for special equipment such as ultra-high temperature reaction, high production safety factor, environmental friendliness and suitability for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde. Background technique [0002] 1H-Pyrazolo[3,4-b]pyridine-3-carbaldehyde (cas number: 1010073-87-6) can be used as a pharmaceutical intermediate of a PIM3 inhibitor for the clinical treatment of pancreatic cancer. There are very few synthetic methods reported. WO2008147822 reported that 2-chloronicotinaldehyde was used as a raw material, which was first ring-closed with hydrazine hydrate to obtain 1H-pyrazolo[3,4-b]pyridine, followed by Grignard reaction after iodination to obtain Target product, its synthetic route is as follows: [0003] [0004] Although this reaction yield is higher, because raw materials such as 2-chloronicotinaldehyde, Grignard reagent and N-piperidine formaldehyde are comparatively expensive, therefore there is the very high problem of production cost. [0005] Therefore, ther...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 李显军庄明晨罗建业郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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