Preparation method of 2-amino-3-fluoropyridine

A fluoropyridine and amino technology, which is applied in the field of preparation technology of 2-amino-3-fluoropyridine, can solve the problems of poor environmental friendliness, high safety risk, complicated post-processing and the like, and achieves high product yield, mild reaction conditions, The effect of suppressing the formation of by-products

Active Publication Date: 2016-06-15
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The technical problem to be solved by the present invention is to provide a synthesis process of 2-amino-3-fluoropyridine to solve the problems of high cost, poor environmental friendliness and safety in the preparation of 2-amino-3-fluoropyridine in the prior art. High risk, cumbersome post-processing and other issues

Method used

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  • Preparation method of 2-amino-3-fluoropyridine
  • Preparation method of 2-amino-3-fluoropyridine
  • Preparation method of 2-amino-3-fluoropyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A. 2-Amino-3-fluoro-5-chloropyridine

[0027] 2,3-Difluoro-5-chloropyridine (100 g, 0.669 mol, 1 eq) and ammonia (1.125 L, 8.025 mol, 12 eq) were added to the autoclave. After airtight, react at 120°C for 20 hours. After the reaction is complete, a light yellow solid precipitates out after cooling. Filter with suction, wash the filter cake with water, extract the filtrate with ethyl acetate, combine the organic layers and dry them with anhydrous sodium sulfate. Evaporate the organic phase under reduced pressure and use Slurry with a small amount of petroleum ether, filter with suction, and collect the obtained filter cake and the precipitated filter cake at the same time to obtain 83.61 g of the compound 2-amino-3-fluoro-5-chloropyridine, with a yield of 85.32%.

[0028] 1 H-NMR (DMSO): 6.442 (s, 2H,); 7.577-7.609 (d, 1H); 7.778-7.785 (d, 1H).

[0029] M / S:147.1[M+H] + .

[0030] B. Preparation of 2-amino-3-fluoropyridine (3)

[0031] Dissolve 2-amino-3-fluoro...

Embodiment 2

[0037] A. 2-Amino-3-fluoro-5-chloropyridine

[0038] 2,3-Difluoro-5-chloropyridine (100 g, 0.669 mol) and ammonia (1.5 L, 10.7 mol) were added to the autoclave. After airtight, react at 140°C for 20 hours. After the reaction is complete, a light yellow solid precipitates out after cooling. Filter with suction, wash the filter cake with water, extract the filtrate with ethyl acetate, combine the organic layers and dry them with anhydrous sodium sulfate. Evaporate the organic phase under reduced pressure and use Slurry with a small amount of petroleum ether, filter with suction, and collect the obtained filter cake and the precipitated filter cake simultaneously to obtain 83.55 g of the compound 2-amino-3-fluoro-5-chloropyridine, with a yield of 85.26%.

[0039] 1 H-NMR (DMSO): 6.442 (s, 2H,); 7.577-7.609 (d, 1H); 7.778-7.785 (d, 1H).

[0040] M / S:147.1[M+H] + .

[0041] B. Preparation of 2-amino-3-fluoropyridine (3)

[0042] Dissolve 2-amino-3-fluoro-5-chloropyridine ...

Embodiment 3

[0048] A. 2-Amino-3-fluoro-5-chloropyridine

[0049] 2,3-Difluoro-5-chloropyridine (100 g, 0.669 mol) and ammonia (1.5 L, 10.7 mol) were added to the autoclave. After sealing, react at 120°C for 24 hours. After the reaction is completed, a light yellow solid precipitates out after cooling. Filter with suction, wash the filter cake with water, extract the filtrate with ethyl acetate, combine the organic layers and dry them with anhydrous sodium sulfate. Evaporate the organic phase under reduced pressure and use Slurry with a small amount of petroleum ether, filter with suction, and collect the obtained filter cake and the precipitated filter cake simultaneously to obtain 83.82 g of the compound 2-amino-3-fluoro-5-chloropyridine, with a yield of 85.53%.

[0050] 1 H-NMR (DMSO): 6.442 (s, 2H,); 7.577-7.609 (d, 1H); 7.778-7.785 (d, 1H).

[0051] M / S:147.1[M+H] + .

[0052] B. Preparation of 2-amino-3-fluoropyridine (3)

[0053] Dissolve 2-amino-3-fluoro-5-chloropyridine ...

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Abstract

The invention discloses a preparation method of 2-amino-3-fluoropyridine, wherein 2,3-difluoro-5-chloropyridine is employed as a raw material and is subjected to an ammoniation reaction with ammonia water, and then a reduction reaction is carried out to prepare the 2-amino-3-fluoropyridine. The preparation method is less in steps, is simple in operation, employs low-cost and easy-to-obtain raw materials, has simple after treatment and high yield and is 77.5% in total yield, and is suitable for large-scale preparation.

Description

technical field [0001] The invention relates to a preparation process of 2-amino-3-fluoropyridine. Background technique [0002] 2-Amino-3-fluoropyridine is an important intermediate of fine chemicals, medicines, pesticides, dyes, and functional materials, and has very broad application prospects in the fields of chemical engineering and pharmaceuticals. In recent years, as an intermediate 2-amino-3-fluoropyridine, it is used in the synthesis of N-heteroaryl amides for the treatment of spinal muscular atrophy, the synthesis of coagulation factor (XIa) inhibitors for the treatment of thromboembolic diseases, and the treatment of central nervous system The synthesis of antagonists of glutamate receptor 2 (mGluR2) and the synthesis of kinase inhibitors have been reported. [0003] At present, the synthesis of 2-amino-3-fluoropyridine mainly has the following three processes: [0004] A. 2-Chloro-3-fluoropyridine (1) and allylamine are used as raw materials to synthesize inter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 赵春深柴慧芳刘力黄筑艳乐意
Owner GUIZHOU UNIV
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