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Synthetic method of 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole

A technology of dimethylphenyl and synthetic method, which is applied in the application field of the synthesis of important intermediates of medetomidine, can solve the problems of cumbersome operation, expensive reagents, unfavorable industrial production, etc., and achieve mild reaction conditions and high yield good effect

Active Publication Date: 2012-05-16
SUNDIA MEDITECH COMPANY LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to disclose a method for synthesizing 4-[1-(2,3-dimethylphenyl)ethylene]-1-R1-2-R2 imidazoles, which mainly solves the problems of expensive reagents and The complicated operation is not conducive to the technical problems of industrial production

Method used

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  • Synthetic method of 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole
  • Synthetic method of 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole

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Embodiment 1

[0014] In a 500 mL three-necked flask, add 0.1 mol of n-butyllithium solution and 200 mL of anhydrous tetrahydrofuran, add 35.7 g of triphenylmethylphosphorus bromide under stirring, and then stir at room temperature for 4 hours. Next, 20 g of 2,3-dimethylphenylimidazol-4-one was added with stirring. After the addition was complete, the reaction was stirred overnight. After the reaction was completed, it was filtered, and the filtrate was concentrated to dryness under reduced pressure. The concentrate was purified by silica gel column (eluent: 5% to 15% by weight methanol dichloromethane) to obtain 17.6g of 4-[1-(2,3-dimethylphenyl)vinyl]imidazole .

Embodiment 2

[0016] In a 500 mL three-necked flask, add 0.1 mol of n-butyl lithium solution and 300 mL of anhydrous tetrahydrofuran, add 35.7 g of triphenylmethylphosphonium bromide under stirring, and then stir at room temperature for 4 hours. Then 44.2 g of 2,3-dimethyl-1-(trityl)imidazol-4-one were added with stirring. After the addition was complete, the reaction was stirred overnight. After the reaction was completed, it was filtered, and the filtrate was concentrated to dryness under reduced pressure. Purify the concentrate through a silica gel column (eluent is petroleum ether ethyl acetate with a concentration of 10% to 20% by weight) to obtain 41 g of 4-[1-(2,3-dimethylphenyl)vinyl]-1 -(trityl)imidazole.

Embodiment 3

[0018] In a 500 mL three-necked flask, add 0.1 mol of n-butyllithium solution and 300 mL of anhydrous tetrahydrofuran, add 35.7 g of triphenylmethylphosphonium bromide under stirring, and then stir at room temperature for 4 hours. Then add 42.1 g of 2,3-dimethylphenyl-1-dimethylsulfonamido-2-tert-butyldimethylsilyl imidazol-4-one under stirring, and the reaction is stirred overnight . After the reaction was completed, it was filtered, and the filtrate was concentrated to dryness under reduced pressure. Purify the concentrate through a silica gel column (eluent is petroleum ether ethyl acetate with a concentration of 5% to 10% by weight) to obtain 35.2g of 4-[1-(2,3-dimethylphenyl)vinyl] -1-Dimethylsulfonamido-2-tert-butyldimethylsilylimidazole.

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Abstract

The invention relates to a synthetic method of 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole, and mainly solves the technical problems of expensive reagents, complex operations, and no benefit to industrial production for existing synthetic methods. The technical scheme of the invention is that: the synthetic method of 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole allows phosphorus ylide and 2,3-dimethylphenyl-1-R1-2-R2 imidazole-4-ketone to react so as to synthesize 4-[1-(2,3-dimethylphenyl)vinyl-1-R1-2-R2 imidazole. The reaction needs stirring overnight (12-16 hours), and the reaction product is filtered, concentrated, washed and purified by a silica gel column. The product is an important intermediate in pharmaceutical synthesis.

Description

technical field [0001] The invention relates to a method for synthesizing medetomidine intermediate 4-[1-(2,3-dimethylphenyl)vinyl]-1-R1-2-R2 imidazole by using ylide reaction, which is mainly used for medetomidine Application in the synthesis of important intermediates of detomidine. Background technique [0002] (±)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole, Chinese name Medetomidine, English name Medetomidine, is considered to be a selective and effective α 2 - Receptor agonists. (+)-(S)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole, the dextro-enantiomer of medetomidine has the following structure: , dexmedetomidine is the active dextroisomer of medetomidine, which has anti-sympathetic, sedative and analgesic effects. The selectivity is stronger, and it is 8 times that of clonidine for α2-adrenergic receptors. In mediating the main pharmacological and therapeutic effects of this product, the α2A receptor subtype plays an important role. The α2A receptor exists in ...

Claims

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Application Information

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IPC IPC(8): C07D233/58C07F7/10
Inventor 卢启轩李国林吴新民施雄伟
Owner SUNDIA MEDITECH COMPANY LTD
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