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2-amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide

A technology of pyridinium bromide and oxoethyl, which is applied in the field of organic synthesis, can solve the problems of difficult synthesis, high market price, and lack of literature and patent reports, and achieve the effects of simple post-processing, stable product quality, and easy control

Inactive Publication Date: 2017-05-10
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This product has great value, but its synthesis is difficult, the market price is expensive, and there is a lack of literature and related patent reports

Method used

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  • 2-amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Dissolve 600mmol (72.0g) of acetophenone in 500mL of dichloromethane, add 2mol of liquid bromine (320g) dropwise at 0°C, and stir for 3 hours after dropping. After the reaction was completed, the solvent was distilled off under reduced pressure to obtain 2,4-dibromoacetophenone. Add 1000 mL N,N-dimethylformamide and stir to dissolve. Add 2mol 2-amino-3,5-dichloropyridine (326g), react at 50°C for 10 hours, after the reaction is completed, cool to room temperature, add 600 mL of water and 500 mL of ethyl acetate for extraction, separate the organic phase, and use Extract with ethyl acetate (3×500 mL), combine the organic phases, wash with water (2×150 mL), wash with 200 mL of saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate the filtrate to obtain 2-amino-3,5 -Dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide crude product, the crude product was treated with n-hexane:ethyl acetate=1:1 (volume ratio) The mixed solution was recrystalli...

Embodiment 2

[0023] 600mmol (72g) acetophenone, dissolved in 1000mL acetonitrile. 2mol liquid bromine (320g) was added dropwise at 0°C. Then react at 20° C. for 6 hours, and remove acetonitrile by rotary evaporation at the end of the reaction to obtain 2,4-dibromoacetophenone. Add 1200 mL of dichloromethane, add 4mol 2-amino-3,5-dichloropyridine (652g), react at 30°C for 15 hours, after the reaction is completed, cool to room temperature, add 600 mL of water and 800 mL of ethyl acetate for extraction, separate The organic phase was taken out, the aqueous phase was extracted with ethyl acetate (3×600 mL), the organic phases were combined, washed with water (2×250 mL), washed with 200 mL saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain 2-Amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide crude product, the crude product by n-hexane:ethyl acetate=1 : 2 (volume ratio) mixed solution recrystallization to obtain pure...

Embodiment 3

[0025] 60mmol (7.2g) of acetophenone, dissolved in 250ml of chloroform. 480 mmol (76.8 g) of liquid bromine was added dropwise at 20°C. The reaction was carried out at 20°C for 5 hours. After the reaction was completed, the solvent was removed by rotary evaporation, 120 mL of acetonitrile was added, and 300 mmol (48.9 g) of 2-amino-3,5-dichloropyridine was reacted at 10°C for 8 hours. After the reaction was completed, 60 mL of water and 60 mL of ethyl acetate were added for extraction, the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (4×20 mL), the combined organic phases were washed with water (2×50 mL), and 100 mL of saturated Wash with brine, dry over anhydrous sodium sulfate, filter, and concentrate the filtrate to obtain 2-amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridine bromide Onium crude product, the crude product was recrystallized from a mixed solution of n-hexane:ethyl acetate=1:1 (volume ratio) to obtain 24.13g of ...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 2-amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide. The preparation method comprises the following steps of dissolving acetophenone in a certain solvent, making the acetophenone react with liquid bromine at subzero 20 to 40 DEG C according to a certain proportion, so as to obtain 2,4-dibromoacetophenone after 2 to 8 hours, in the certain solvent, making the 2,4-dibromoacetophenone react with a certain proportion of 2-amino-3,5-dichloropyridine for 3 to 15 hours at 0 to 80 DEG C, terminating the reaction, cooling an obtained first mixture to room temperature, extracting the first mixture with ethyl acetate, washing a substance through water and saturated salt water, drying the substance with anhydrous sodium sulfate, carrying out rotary evaporation and concentration to subsequently obtain a product provided by the invention, and recrystallizing the coarse product to obtain a pure product. Raw materials in the reaction are relatively easy to obtain; the price is reasonable; the condition of the reaction is mild; the operation is easy; the control is easy; the post treatment is simple; further, the quality of the product is stable; the purity is high.

Description

[0001] (1) Technical field [0002] The invention relates to the field of organic compound synthesis, in particular to a preparation method of 2-amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide. [0003] (2) Background technology [0004] 2-Amino-3,5-dichloro-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide is an important intermediate in organic synthesis, mainly used in the production of pharmaceutical intermediates Indolizine derivatives, coumarin derivatives and spices, etc. Indolizine derivatives showing a broad spectrum of biological activities for substituted indolizin-3-yl(phenyl)methanones were designed and synthesized to inhibit human farnesyltransferase. Recently, similar indolizines have been patented for the treatment of cancer, cardiovascular disease and degenerative joint diseases such as osteoarthritis or spondyloarthritis. The mechanism of inhibition involves basic fibroblast growth factor and leukotrienes production. Other substituted...

Claims

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Application Information

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IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 谈平忠韩猛耿宣平程伟来新胜来超来子腾
Owner SHANDONG YOUBANG BIOCHEM TECH
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