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3-trifluoromethyl quinoxalinone compound preparation method

A technology of trifluoromethylquinoxalinone and quinoxalinone, which is applied in the field of preparation of 3-trifluoromethylquinoxalinone compounds, can solve problems such as difficult operation and expensive hexafluoropropylene oxide, and achieve The effect of mild conditions and simple post-processing

Active Publication Date: 2018-12-11
HEBEI UNIV OF TECH
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Problems solved by technology

[0005] However, hexafluoropropylene oxide is an expensive and irritating gaseous reagent that is not easy to handle under laboratory conditions

Method used

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Embodiment 1

[0026] Add the substrate 1-methylquinoxalin-2(1H)-one to a 15 ml reaction tube (48.0 mg, 0.3 mmol, the substituent R on the structural formula 1 is methyl, R 2 is a hydrogen atom), sodium trifluoromethanesulfinate (CF 3 SO 2 Na, 140.5 mg, 0.9 mmol), and the oxidant iodobenzene bistrifluoroacetate (387.0 mg, 0.9 mmol) was added, the oil pump was evacuated, argon was filled, and repeated 3 times, 3 ml of acetonitrile was added with a syringe. The mixture was stirred at room temperature under argon for 12 hours. Thin-layer chromatography detects that the reaction is substantially complete, and the solvent acetonitrile is removed by rotary evaporation, and the column chromatography (ethyl acetate / petroleum ether=1 / 3) is directly used to obtain the product 1-methyl-3-trifluoromethylquinoxaline- 2(1H)-keto 54.8 mg, total yield 80%.

[0027] The hydrogen nuclear magnetic resonance spectrum data of gained product is 1 H NMR (400MHz, CDCl 3 )δ: 8.05(dd, J=1.2Hz, J=44Hz, 1H), ...

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Abstract

The invention discloses a 3-trifluoromethyl quinoxalinone compound preparation method which comprises the following steps of in an inert gas atmosphere, adding a quinoxalinone compound, sodium trifluoromethanesulfinate and an oxidant in a solvent, performing reaction for 6-18 h at the temperature of 0-75 DEG C, and performing column chromatography separation and purification to obtain 3-trifluoromethyl substituted quinoxalinone compound. The 3-trifluoromethyl quinoxalinone compound preparation method provided by the invention is low in reagent cost, mild in reaction condition and simple in aftertreatment and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method for obtaining 3-trifluoromethylquinoxalinone compounds through trifluoromethylation of quinoxalinone compounds. Background technique [0002] The trifluoromethyl group has a strong electron-withdrawing ability, and has the characteristics of lipophilicity, hydrophobicity, and good stability. The introduction of trifluoromethyl groups into potential candidate drug molecules can obviously adjust the physical, chemical and biological properties of these candidate drug molecules. Drug molecules containing trifluoromethyl groups play a very important role in the pharmaceutical field. The quinoxalinone series derivative C substituted with trifluoromethyl at the 3rd position of the parent ring of quinoxalinone is a new type 1 AIDS reverse transcriptase inhibitor. The key intermediate in its synthetic process is 3-trifluoromethylquinoxalinone compound B, and the existing method of synthesizing this type of compoun...

Claims

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Application Information

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IPC IPC(8): C07D241/44
CPCC07D241/44
Inventor 张宏宇王李平张月成赵继全
Owner HEBEI UNIV OF TECH
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