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Preparation method of 6-fluoro-3-iodine-2-methoxypyridine

A technology of methoxypyridine and n-butyllithium, applied in the direction of organic chemistry and the like, can solve the problems of time-consuming and labor-intensive purification methods, high synthesis cost, poor selectivity, etc., to simplify post-processing operations and purification methods, and to solve synthetic problems Cost issue, highly selective effect

Pending Publication Date: 2022-07-29
山东百启生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are only a very small amount of products on the market, and the commonly used synthetic methods have low yields and poor selectivity, and the purification methods are time-consuming and labor-intensive, and the synthesis costs are high

Method used

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  • Preparation method of 6-fluoro-3-iodine-2-methoxypyridine
  • Preparation method of 6-fluoro-3-iodine-2-methoxypyridine
  • Preparation method of 6-fluoro-3-iodine-2-methoxypyridine

Examples

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Effect test

Embodiment 1

[0024] A kind of preparation method of 6-fluoro-3-iodo-2-methoxypyridine, its concrete steps are:

[0025] Vacuum the 3L three-neck glass flask to -0.07Mpa with a circulating water vacuum pump, break the vacuum with nitrogen, and repeat the cycle three times; then vacuum the reaction flask to -0.06Mpa; then add 2, 2, 6, 6- The THF (290ml) solution of tetramethylpiperidine (144.5g, 1022.7mmol) was sucked into the reaction flask, and the reaction device was replaced by nitrogen three times; the reaction flask was cooled to -50°C with liquid nitrogen; Add n-butyllithium (409ml, 1022.7mmol) in n-hexane solution, control the temperature to -50°C during the dropwise addition; after dropping, stir at -50°C for 60 minutes; then continue to cool down to -85°C, add 2-fluoro- A solution of 6-methoxypyridine (100g, 786.7mmol) in THF (300ml) was slowly dropped into the reaction flask, pay attention to temperature control at -85°C, and stir the reaction at -85°C for 60 minutes; then add iod...

Embodiment 2

[0027] A kind of preparation method of 6-fluoro-3-iodo-2-methoxypyridine, its concrete steps are:

[0028] Vacuum the 3L three-neck glass flask to -0.06Mpa with a circulating water vacuum pump, break the vacuum with nitrogen, and repeat the cycle three times; then vacuum the reaction flask to -0.05Mpa; The THF (400ml) solution of tetramethylpiperidine (133.3g, 944.04mmol) was sucked into the reaction flask, and the reaction device was replaced by nitrogen for 3 times; the reaction flask was cooled to -40°C with liquid nitrogen; Add the n-hexane solution of n-butyllithium (409ml, 1022.7mmol), control the temperature to -40°C during the dropwise addition; after the dropwise addition, stir at -40°C for 70 minutes; then continue to cool down to -75°C, add 2-fluoro- A solution of 6-methoxypyridine (100g, 786.7mmol) in THF (400ml) was slowly dropped into the reaction flask, pay attention to temperature control at -75°C, and stir the reaction at -75°C for 65 minutes; then add iodine ...

Embodiment 3

[0030] A kind of preparation method of 6-fluoro-3-iodo-2-methoxypyridine, its concrete steps are:

[0031] Vacuum the 3L three-neck glass flask to -0.06Mpa with a circulating water vacuum pump, break the vacuum with nitrogen, and repeat the cycle three times; then vacuum the reaction flask to -0.06Mpa; The THF (350ml) solution of tetramethylpiperidine (155.6g, 1101.38mmol) was sucked into the reaction flask, and the reaction device was replaced with nitrogen three times; the reaction flask was cooled to -45°C with liquid nitrogen; Add n-butyllithium (409ml, 1022.7mmol) in n-hexane solution, and control the temperature to -45°C during the dropwise addition; after dropping, stir at -45°C for 80 minutes; then continue to cool down to -80°C, add 2-fluoro- A solution of 6-methoxypyridine (100g, 786.7mmol) in THF (350ml) was slowly dropped into the reaction flask, pay attention to temperature control at -80°C, and stir the reaction at -80°C for 70 minutes; then add iodine (279.8g, ...

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Abstract

The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of 6-fluoro-3-iodine-2-methoxypyridine, which comprises the following steps: under the condition of negative pressure, dropwise adding an n-hexane solution of n-butyllithium into a THF solution of 2, 2, 6, 6-tetramethylpiperidine, then cooling, slowly dropwise adding a THF solution of 2-fluoro-6-methoxypyridine and a THF solution of iodine, and carrying out post-treatment to obtain the 6-fluoro-3-iodine-2-methoxypyridine. And carrying out condensation so as to obtain the 6-fluoro-3-iodine-2-methoxypyridine. The invention provides the method for synthesizing the 6-fluoro-3-iodine-2-methoxypyridine with high yield and high selectivity, so that the market blank is filled, the problem of synthesis cost is solved, and the post-treatment operation and the purification method are simplified.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and in particular relates to a preparation method of 6-fluoro-3-iodo-2-methoxypyridine. Background technique [0002] 1-[(3R,4S)-4-cyanotetrahydropyran-3-yl]-3-[(2-fluoro-6-methoxy-4-pyridyl)-amino]pyrazole-4- Formamide is a selective Janus kinase (JAK) inhibitor, so it can be used to treat JAK-mediated diseases, such as anticancer, antiviral, etc. 6-Fluoro-3-iodo-2-methoxypyridine can be used as a key intermediate in the synthesis of such compounds, and can be derivatized to provide more derivative compounds for the research and development of antiviral and anticancer drugs . At present, there is only a very small supply of products on the market, and the currently commonly used synthetic methods have low yields, poor selectivity, time-consuming and labor-intensive purification methods, and high synthesis costs. SUMMARY OF THE INVENTION [0003] In view of the above problem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64
CPCC07D213/64
Inventor 吴冬冬郭立涛崔宁宁
Owner 山东百启生物医药有限公司
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