Preparation method of 2' 4'-difluoro-2-[1-(1H-1, 2, 4-triazolyl)] acetophenone

A technology based on difluoroacetophenone and triazole, which is applied in the field of organic compound synthesis to achieve good social and economic benefits, convenient operation, and great potential for economic value

Pending Publication Date: 2020-08-11
HUNAN FURUI BIOPHARMA TECH CO LTD
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Problems solved by technology

[0006] One of the important intermediates for the synthesis of voriconazole is 2'4'-difluoro-2-[1-(1H-1,2,4-triazolyl)]acetophenone. Currently, there are few relevant literatures disclosing its preparation. method

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  • Preparation method of 2' 4'-difluoro-2-[1-(1H-1, 2, 4-triazolyl)] acetophenone
  • Preparation method of 2' 4'-difluoro-2-[1-(1H-1, 2, 4-triazolyl)] acetophenone
  • Preparation method of 2' 4'-difluoro-2-[1-(1H-1, 2, 4-triazolyl)] acetophenone

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[0029] Its preparation method comprises the following steps:

[0030] Q1. At the reaction temperature, select 2-chloro-2'4'-difluoroacetophenone as the raw material, and react with 3-chloro-1,2,4-triazole under the condition of the reaction solvent. During the reaction, Using potassium carbonate as a base to introduce into the reaction mixture, the reaction temperature is 10-40°C, and the reaction time is 5-7 hours;

[0031] Q2, 2-(3-chloro-1H-1,2,4-triazole-1-)-1-(2,4-difluorophenyl)ethanone is carried out in alcohol solvent, hydrogen environment, palladium carbon catalysis Dehalogenation reaction to obtain the final product 2'4'-difluoro-2-[1-(1H-1,2,4-triazolyl)]acetophenone, the reaction temperature is 40~75°C, and the reaction time is 2 to 5 hours.

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Abstract

The invention provides a preparation method of 2' 4'-difluoro-2-[1-(1H-1, 2, 4-triazolyl)] acetophenone. 2-chloro-2' 4'-difluoroacetophenone serving as a raw material reacts with 3-chloro-1, 2, 4-triazole to obtain 2-(3-chloro-1H-1, 2, 4-triazolyl-1-(2, 4-difluorophenyl) ethanone, and then palladium-on-carbon hydrogenation dehalogenation is carried out to obtain a final product 2' 4'-difluoro-2-[1-(1H-1, 2, 4-triazolyl) acetophenone. The method for preparing 2' 4'-difluoro-2-[1-(1H-1, 2, 4-triazolyl)] acetophenone is simple in steps, convenient to operate, low in economic cost, suitable for industrial production, capable of bringing good social benefits and economic benefits and large in economic value potential.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, more specifically, to a voriconazole intermediate 2'4'-difluoro-2-[1-(1H-1,2,4-triazolyl)]acetophenone method of preparation. Background technique [0002] Voriconazole is a broad-spectrum triazole antifungal drug developed by Pfizer of the United States. Its indications are as follows: 1. Treatment of invasive aspergillosis; 2. Treatment of fluconazole-resistant Candida. Severe invasive infections (including Candida krusei); 3. Treatment of severe infections caused by actinomycetes and Fusarium. It is mainly used for the treatment of progressive and potentially life-threatening infections in immunocompromised patients, bringing good news to patients with severe fungal infections. [0003] The Chinese name of Voriconazole is (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4 -Triazol-1-yl)-2-butanol, its molecular formula is C 16 h 14 f 3 N 5 O, CAS num...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08
CPCC07D249/08
Inventor 鲁光英周跃辉
Owner HUNAN FURUI BIOPHARMA TECH CO LTD
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