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A kind of synthetic method of the medicine intermediate compound containing trifluoroethyl

A synthetic method, trifluoroethyl technology, applied in the synthesis of pharmaceutical intermediate compounds, the field of synthesis of pharmaceutical intermediates, can solve the problems of harsh reaction conditions, low reaction yield, etc., to improve the reaction yield, overcome the yield low rate effect

Active Publication Date: 2015-11-25
BTC PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although there are many CF in the prior art 3 CH 2 Catalyzed coupling reaction with aromatic hydrocarbons to obtain the method of trifluoroethyl-containing intermediate compound, but these methods or techniques have low reaction yield, harsh reaction conditions or the use of noble metal catalysts, etc., the inventors aimed at the above problems, aiming to On the basis of improving the yield and process conditions of the existing technology, and fully studying the literature and exploring the experimental conditions, a new composite catalytic system was developed to realize the CF 3 CH 2 High-efficiency coupling reaction with aromatic hydrocarbons to obtain the synthesis method of pharmaceutical intermediate compounds containing trifluoroethyl groups, which has a very wide range of industrial application prospects and research value

Method used

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  • A kind of synthetic method of the medicine intermediate compound containing trifluoroethyl
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  • A kind of synthetic method of the medicine intermediate compound containing trifluoroethyl

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] Under the atmosphere of argon gas, add 1mmol formula (I) compound, 2.2mmol 120 mesh copper powder and 4.5ml solvent DMF to the reactor, then add 3mmol CF 3 CH 2 1, finally adding 80mg mass ratio is the auxiliary agent mixture of tricyclohexylphosphine, zirconium dioxide and ethylene glycol di-n-octyl sodium succinate sulfosuccinate of 1:0.4:1.3, keep the inert atmosphere after continuing to evacuate for 10min and The temperature was raised to 95°C and the reaction was stirred for 18 hours. After the reaction was completed, it was cooled and ethyl acetate was added to the mixture. After filtration, the product layers were combined, washed with water, and dried with anhydrous magnesium sulfate. The organic layer was concentrated in vacuo, and the residue was purified by silica gel column chromatography. The compound of formula (II) can be obtained with a yield of 98.5% and a purity of 99.3% (HPLC).

[0036] 1 HNMR (500MHz, CDCl 3 )δ7.35(d, J=8.3Hz, 2H), 7.2...

Embodiment 2

[0038]

[0039] Under argon gas atmosphere, add 1mmol formula (I) compound, 2.5mmol 100 mesh copper powder and 4ml solvent DMF to the reaction kettle, then add 3.3mmol CF 3 CH 2 1, finally adding 90mg mass ratio is the auxiliary agent mixture of tricyclohexylphosphine, zirconium dioxide and ethylene glycol di-n-octyl sodium succinate sulfosuccinate of 1:0.4:1.3, keep the inert atmosphere after continuing to evacuate for 10min and The temperature was raised to 100°C and the reaction was stirred for 24 hours. After the reaction was completed, it was cooled and ethyl acetate was added to the mixture. After filtration, the product layers were combined, washed with water, and dried with anhydrous magnesium sulfate. The organic layer was concentrated in vacuo, and the residue was purified by silica gel column chromatography. The compound of formula (II) can be obtained with a yield of 98.9% and a purity of 99.1% (HPLC).

[0040] 1 HNMR (400MHz, CDCl 3 )δ7.65(d, J=8.3Hz, 2H), 7.4...

Embodiment 3

[0042]

[0043] Under argon gas atmosphere, add 1mmol formula (I) compound, 2.4mmol 150 mesh copper powder and 5ml solvent DMF to the reaction kettle, then add 3.5mmol CF 3 CH 2 1, finally adding 70mg mass ratio is the auxiliary agent mixture of tricyclohexylphosphine, zirconium dioxide and ethylene glycol di-n-octyl sodium succinate sulfosuccinate of 1:0.4:1.3, keep the inert atmosphere after continuing to evacuate for 10min and The temperature was raised to 90°C and the reaction was stirred for 22 hours. After the reaction was completed, it was cooled and ethyl acetate was added to the mixture. After filtration, the product layers were combined, washed with water, and dried with anhydrous magnesium sulfate. The organic layer was concentrated in vacuo, and the residue was purified by silica gel column chromatography. The compound of formula (II) can be obtained with a yield of 98.7% and a purity of 98.9% (HPLC).

[0044] 1 HNMR (400MHz, CDCl 3 )δ10.01(s,1H),7.86(d,J=7.0...

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Abstract

The invention relates to a synthesis method of a pharmaceutical intermediate compound containing trifluoromethyl, which directly implements a coupling reaction between aryl iodine and 1,1,1-trifluoro-2-ethyl iodide. According to the method, a copper powder / additive system serves as a multi-composite catalysis system to realize efficient coupling between aryl iodine and 1,1,1-trifluoro-2-ethyl iodide; reaction time is shortened on the basis of improving a reaction yield. Dimethyl formamide (DMF) in the process is an optimum reaction solvent, and various components of additive are selected according to an optimum industrial formula; the compound shows outstanding industrial application potential and theoretical research value.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate, in particular to a method for synthesizing a trifluoroethyl-containing pharmaceutical intermediate compound, and belongs to the field of organic synthesis of pharmaceutical intermediate compounds. Background technique [0002] The introduction of fluorine atoms into organic molecules or drug molecules can greatly change the physical and chemical properties of compounds, such as metabolic stability, biocompatibility, etc., so this strategy is widely used in the design of drug compounds. In recent years, the trifluoromethyl group has aroused the interest of many researchers due to the strong electron-withdrawing properties and hydrophobic properties of its functional groups. In addition, many studies have also focused on the trifluoromethylation reaction of aromatic compounds, so that the preparation reaction of 2,2,2-trifluoroethyl aromatic compounds has also received wide...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C22/08C07C17/269C07C255/50C07C253/30C07C47/55C07C45/63C07C205/11C07C201/12
Inventor 郑攀锋
Owner BTC PHARMA TECH CO LTD
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