Nankai University

Xiaochen Wang

Xinyue Zhou

Junjie Tian

Zhong Liu

Jiahao He

A method for preparing a meta-functionalized pyridine compound is provided. The method has a first step, S1, for preparation of 1,4-dihydropyridine, involving: in a glove box filled with nitrogen, adding a catalyst, a solvent, pinacolborane and pyridine to a reaction flask in order and stirring the mixture at 40-110° C. for a reaction for 5-12 hours to obtain 1,4-dihydropyridine. In a second step, S2, catalyzed functionalization of pyridine at the meta-position is provided by adding an imine, an aldehyde, a ketone or a halogenation reagent to the above reaction flask, and stirring the mixture in a nitrogen atmosphere until the reaction is completed; and performing distillation under reduced pressure to remove the solvent and column chromatography separation to obtain a meta-functionalized pyridine, wherein the reaction temperature is 40-110° C., and the reaction time is 5-24 hours.

Method for preparing meta-functionalized pyridine compound

A method for preparing a pyridine compound substituted with trifluoromethylthio, difluoromethylthio or trifluoromethyl in the meta position is provided, which includes S1. in a glove box filled with nitrogen, adding a catalyst, a solvent, pinacolborane, and pyridine to a reaction flask, stirring the mixture, and performing a reaction at 40-100° C. for 2-12 hours to obtain dihydropyridine; S2. adding a trifluoromethylthio reagent, a difluoromethylthio reagent, or a trifluoromethyl reagent to the reaction flask, stirring the mixture, and performing a reaction at room temperature to 80° C. for 2-12 hours to obtain trifluoromethylthio-, difluoromethylthio- or trifluoromethyl-substituted dihydropyridine; and S3. placing the reaction flask in the air or adding 2,3-dichloro-5,6-dicyanobenzoquinone, stirring same, and performing a reaction at room temperature for 4-12 hours, followed by distillation under reduced pressure to remove the solvent and column chromatography separation to obtain the meta-substituted pyridine compound.

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Tianjin, China

Xiaochen Wang