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Preparation method of pyridinium 2-animo-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)bromide

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

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

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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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  • Preparation method of pyridinium 2-animo-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)bromide

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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-5-iodopyridine (440g), 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 ethyl acetate for the aqueous phase Extract (3×500 mL), combine the organic phases, wash with water (2×150 mL), wash with 200 mL saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate the filtrate to obtain 2-amino-5-iodo-1- (2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide crude product, the crude product was recrystallized from a mixed solution of n-hexane:ethyl acetate=1:1 (volume ratio) to obt...

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-5-iodopyridine (880g), 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, The aqueous phase was extracted with ethyl acetate (3×600 mL), the organic phases were combined, washed with water (3×250 mL), washed with 300 mL saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain 2-amino- 5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide crude product, the crude product is hexane:ethyl acetate=1:2 (volume ratio) The mixed solution was recrystallized to obtain 262.9 g of pure product, wit...

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 (66.0 g) of 2-amino-5-iodopyridine 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 crude product of 2-amino-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide , the crude product was recrystallized from a mixed solution of n-hexane:ethyl acetate=1:1 (volume ratio) to obtain 28.4g of pure product,...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of pyridinium 2-animo-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)bromide. The method comprises the following steps: dissolving acetophenone in a certain solvent, and carrying out reaction with liquid bromine according to a certain ratio at -20-40 DEG C for 2-8 hours to obtain 2,4-dibromoacetophenone; in a certain solvent, carrying out reaction with 2-amino-5-iodopyridine according to a certain ratio at 0-80 DEG C for 3-15 hours; after the reaction finishes, cooling to room temperature, extracting with ethyl acetate, washing with water and a saturated saline solution, drying with anhydrous sodium sulfate, and carrying out rotary evaporation concentration to obtain the pyridinium 2-animo-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)bromide crude product; and recrystallizing the crude product to obtain the pure product. The method has the advantages of accessible reaction raw materials, reasonable price, mild reaction conditions and simple after-treatment, and is easy to operate and control; and the product has the advantages of stable quality and high purity.

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-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide. [0003] (2) Background technology [0004] 2-Amino-5-iodo-1-(2-(4-bromophenyl)-2-oxoethyl)pyridinium bromide is an important intermediate in organic synthesis, mainly used in the production of indolizine, a pharmaceutical intermediate 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 indolazin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 谈平忠程伟韩猛来新胜来超来子腾
Owner SHANDONG YOUBANG BIOCHEM TECH
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