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A method for preparing 3-dibromomethyl imidazo[1,2-α]pyridine derivatives

A technology for dibromomethyl imidazoles and derivatives, applied in the direction of organic chemistry and the like, can solve the problems of harsh reaction conditions, low yield and high cost, and achieve the effects of easy separation, simple reaction conditions and simple post-processing

Active Publication Date: 2021-11-12
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the method for synthesizing imidazo[1,2-a]pyridine is mainly prepared from α-halogenated acetophenone and 2-aminopyridine through cyclocondensation reaction, but the existing method still has shortcomings, such as cost High, harsh reaction conditions, low yield and other disadvantages

Method used

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  • A method for preparing 3-dibromomethyl imidazo[1,2-α]pyridine derivatives
  • A method for preparing 3-dibromomethyl imidazo[1,2-α]pyridine derivatives
  • A method for preparing 3-dibromomethyl imidazo[1,2-α]pyridine derivatives

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Experimental program
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Effect test

Embodiment 1

[0021] Add potassium carbonate 41mg, 4-methyl-N-[2-phenyl-1-(pyridin-2-ylamino)-ethylene]-benzenesulfonamide 73mg and carbon tetrabromide 79mg in 10ml reaction bottle , then add 2ml of dichloromethane solvent, nitrogen replacement three times; under nitrogen protection conditions, the reaction mixture was stirred at 100 ℃ for 12h, and the reaction process was followed by thin layer chromatography until the end of the reaction (developing agent was sherwood oil / ethyl acetate The volume ratio is 2:1), after the reaction, the reaction mixture was cooled to room temperature, filtered, and the solvent was removed under reduced pressure to obtain the crude product; the crude product was separated by column chromatography on silica gel column chromatography, and the volume ratio was 2 : 1 petroleum ether and ethyl acetate as eluent until the final product 3-dibromomethyl imidazo[1,2-α]pyridine derivatives, specifically (Z)-N-(3-( The yield of dibromomethyl)-3-phenylimidazo[1,2-α]pyri...

Embodiment 2

[0026] Add potassium carbonate 41mg, N-[2-(4-ethyl-phenyl)-1-(pyridin-2-ylamino)-ethylidene]-4-methyl-benzenesulfonamide to a 10ml reaction flask 78mg and 79mg of carbon tetrabromide, then 2ml of dichloromethane solvent was added, and nitrogen was replaced three times; under nitrogen protection, the reaction mixture was stirred at 100°C for 12h. The reaction process was tracked by thin-layer chromatography until the end of the reaction (the volume ratio of sherwood oil / ethyl acetate as the developing agent was 2:1), after the end of the reaction, the reaction mixture was cooled to room temperature, filtered, and the solvent was removed under reduced pressure to obtain crude Product; The crude product is separated by column chromatography on a silica gel column chromatography, with a volume ratio of 2:1 petroleum ether and ethyl acetate as eluent, until the final product 3-dibromomethyl imidazo[1 ,2-α]pyridine derivatives, specifically (Z)-N-(3-(dibromomethyl)-3-(4-ethylphenyl)...

Embodiment 3

[0031]Add 41 mg of potassium carbonate and 80 mg of N-[2-(4-chloro-phenyl)-1-(pyridin-2-ylamino)-ethylidene]-4-methyl-benzenesulfonamide to a 10 ml reaction flask And carbon tetrabromide 79mg, then add dichloromethane solvent 2ml, nitrogen replacement three times; under the condition of nitrogen protection, the reaction mixture was stirred at 100 ℃ for 12h. The reaction process was tracked by thin-layer chromatography until the end of the reaction (the volume ratio of sherwood oil / ethyl acetate as the developing agent was 2:1), after the end of the reaction, the reaction mixture was cooled to room temperature, filtered, and the solvent was removed under reduced pressure to obtain crude Product; The crude product is separated by column chromatography on a silica gel column chromatography, with a volume ratio of 2:1 petroleum ether and ethyl acetate as eluent, until the final product 3-dibromomethyl imidazo[1 ,2-α]pyridine derivatives, specifically (Z)-N-(3-(4-chlorophenyl)-3-(d...

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Abstract

The invention provides a method for preparing 3-dibromomethyl imidazo[1,2-α]pyridine derivatives, which is characterized in that, comprising: adding R 1 , R 2 , R 3 Substituted N‑(2‑pyridyl)amidines, CBr 4 , an organic solvent and a catalyst, under nitrogen protection conditions, react at 100-120°C for 8-16h, after the reaction, filter, concentrate, and separate by column chromatography to obtain 3-dibromomethyl imidazo[1,2 ‑α]pyridine derivatives.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a method for preparing 3-dibromomethyl imidazo[1,2-α]pyridine derivatives. Background technique [0002] Imidazo[1,2-α]pyridine and its derivatives are a class of substances with special structural motifs, which are used in many compounds because of their wide range of pharmaceutical and biological properties, especially imidazo[1,2 The potent anticancer and antiviral activities highlighted by -α]pyridine, such as antibacterial, antiviral, antituberculosis, antitumor, thus imidazo[1,2-α]pyridine can be said to be a valuable cornerstone in drug discovery. In addition, imidazo[1,2-α]pyridine derivatives are also widely used in organic synthesis and materials science. At present, the method for synthesizing imidazo[1,2-a]pyridine is mainly prepared from α-halogenated acetophenone and 2-aminopyridine through cyclocondensation reaction, but the existing method still has shortcomings,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 易封萍付超孙启辉孙静易维银
Owner SHANGHAI INST OF TECH
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