Synthetic process of 5-bromo-3-methyl-1h-pyrazolo[3,4-b]pyridine

A synthesis process, pyrazolo technology, applied in the field of synthesis process of pyrazolo pyridine derivatives, can solve the problems of unfavorable large-scale production and application, low yield, etc., and achieve the effect of low cost and simple operation steps

Active Publication Date: 2017-12-15
上海泰坦科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the synthetic methods of pyrazolopyridine compounds mainly contain two categories, one is to synthesize pyridine ring on the basis of pyrazole ring, and the other is to synthesize pyrazole ring on the basis of pyridine ring, but these methods When synthesizing 5-bromo-3-methyl-1H-pyrazolo[3,4-B]pyridine, the operation steps and yield are also low, which is not conducive to large-scale production and application in industry

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  • Synthetic process of 5-bromo-3-methyl-1h-pyrazolo[3,4-b]pyridine

Examples

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Embodiment 1

[0014] This example relates to a synthesis process of 5-bromo-3-methyl-1H-pyrazolo[3,4-B]pyridine, which consists of the following steps: 0.1mol 5-bromo-3-ethynyl-2 -Chloro-pyridine was put into a 500mL reaction bottle, added to 100mL DMF, and then sequentially added 0.1mol hydrazine, 0.05mol calcium carbonate and 0.008mol aluminum silicate, mixed evenly, then reacted at 4°C for 30 hours, filtered to remove insoluble matter, and Evaporate the solvent under pressure, recrystallize once with 50mL ethanol, and dry overnight at 35°C to obtain 18.2g of white 5-bromo-3-methyl-1H-pyrazolo[3,4-B]pyridine with a yield of 85.3% , purity 99.6%, MS: m / z=212 (M + ); 1 H-NMR (300 MHz, DMSO) δ: 8.16 (s, 1H), 7.58 (s, 1H), 1.05 (s, 3H).

Embodiment 2

[0016] This example relates to a synthesis process of 5-bromo-3-methyl-1H-pyrazolo[3,4-B]pyridine, which consists of the following steps: 0.1mol 5-bromo-3-ethynyl-2 -Chloro-pyridine was put into a 500mL reaction flask, added to 100mL DMF, then added 0.1mol hydrazine, 0.05mol calcium carbonate and 0.02mol aluminum silicate in sequence, mixed well, then reacted at 6°C for 24 hours, filtered to remove insoluble matter, and reduced Evaporate the solvent under pressure, recrystallize once with 50mL ethanol, and dry overnight at 35°C to obtain 17.6g of white 5-bromo-3-methyl-1H-pyrazolo[3,4-B]pyridine with a yield of 82.7% , purity 99.5%, MS: m / z=212 (M + ); 1 H-NMR (300 MHz, DMSO) δ: 8.16 (s, 1H), 7.57 (s, 1H), 1.04 (s, 3H).

Embodiment 3

[0018] This example relates to a synthesis process of 5-bromo-3-methyl-1H-pyrazolo[3,4-B]pyridine, which consists of the following steps: 0.1mol 5-bromo-3-ethynyl-2 -Chloro-pyridine was put into a 500mL reaction flask, added to 100mL DMF, and then sequentially added 0.1mol hydrazine, 0.05mol calcium carbonate and 0.003mol aluminum silicate, mixed well, then reacted at 2°C for 27 hours, filtered to remove insoluble matter, and Evaporate the solvent under pressure, recrystallize once with 50mL of ethanol, and dry overnight at 35°C to obtain 17.9g of white 5-bromo-3-methyl-1H-pyrazolo[3,4-B]pyridine with a yield of 84.1% , purity 99.6%, MS: m / z=212 (M + ); 1 H-NMR (300 MHz, DMSO) δ: 8.15 (s, 1H), 7.59 (s, 1H), 1.05 (s, 3H).

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Abstract

The invention relates to a synthesizing process of 5-bromo-3-methyl-1H-pyrazolo [3, 4-B] pyridine. The synthesizing process comprises the following steps: 5-bromine-3-acetenyl-2-chlorine-pyridine is dissolved into DMF, then hydrazine, calcium carbonate and aluminium silicate are added sequentially and mixed uniformly, the mixture is reacted for 24-36 hours at the temperature of 1 DEGC to 10 DEG C, insoluble substances are filtered, the pressure is reduced to steam a solvent, and ethyl alcohol is used for recrystallization, so that the 5-bromo-3-methyl-1H-pyrazolo [3, 4-B] pyridine can be obtained. According to the synthesizing process, the aluminium silicate is used as a catalyst, so that the operation steps are simple, the yield is higher and industrial large-scale production of the 5-bromo-3-methyl-1H-pyrazolo [3, 4-B] pyridine is facilitated.

Description

technical field [0001] The invention relates to a synthesis process of pyrazolopyridine derivatives, in particular to a synthesis process of 5-bromo-3-methyl-1H-pyrazolo[3,4-B]pyridine. Background technique [0002] In recent years, fused heterocyclic compounds have aroused the interest of medical and pesticide researchers due to their remarkable physiological activities. Among them, pyrazolopyridine compounds are a kind of fused heterocyclic compounds that have been studied a lot. Pharmacological studies have shown that compounds with the basic structure of pyrazolopyridine have bactericidal, herbicidal, antifungal, anti-inflammatory, antiallergic, antimalarial, anxiolytic, antithrombotic, antihypotensive, antibacterial, analgesic, and antiplatelet properties And many other activities, therefore, pyrazolopyridine compounds are a class of compounds with high research value. According to the ring type of pyrazolopyridine compounds, they can be mainly divided into the followi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 谢应波张庆张华徐肖冰罗桂云
Owner 上海泰坦科技股份有限公司
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