A kind of preparation technology of 2-amino-3-fluoropyridine

A technology of fluoropyridine and amino, which is applied in the field of preparation technology of 2-amino-3-fluoropyridine, can solve the problems of poor environmental friendliness, cumbersome post-processing, high safety risk, etc., and achieve high product yield and suppress by-products Formation and mild reaction conditions

Active Publication Date: 2018-06-22
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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  • A kind of preparation technology of 2-amino-3-fluoropyridine
  • A kind of preparation technology of 2-amino-3-fluoropyridine
  • A kind of preparation technology 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 sealing, the reaction was carried out at 120 °C for 20 h. After the reaction was completed, a pale yellow solid was precipitated after cooling. The filter cake was washed with water by suction filtration, and the filtrate was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. A small amount of petroleum ether was slurried, filtered with suction, and the obtained filter cake and the separated filter cake were collected simultaneously to obtain 83.61 g of 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] In a 1000ml single-neck flask, 2-amino-3-fluoro-5...

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 sealing, the reaction was carried out at 140 °C for 20 h. After the reaction was completed, a pale yellow solid was precipitated after cooling. The filter cake was washed with water, and the filtrate was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The organic phase was evaporated under reduced pressure and used A small amount of petroleum ether was slurried, filtered with suction, and the obtained filter cake and the separated filter cake were collected simultaneously to obtain 83.55 g of 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] In a 1000ml single-nec...

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 (50g,...

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PUM

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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 in fine chemicals, pharmaceuticals, pesticides, dyes, and functional materials, and has a very broad application prospect in the fields of chemical engineering and pharmaceuticals. In recent years, as an intermediate 2-amino-3-fluoropyridine, it has been used in the synthesis of N-heteroarylamides 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 blocked glutamate receptor 2 (mGluR2) antagonists and the synthesis of kinase inhibitors have been reported. [0003] At present, the synthesis of 2-amino-3-fluoropyridine mainly includes the following three processes: [0004] A. 2-Chloro-3-fluoropyridine (1) and allylamine are used as raw materi...

Claims

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Application Information

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Patent Type & Authority Patents(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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