A kind of quinoline derivative and its preparation method and application
A derivative and quinoline technology, applied in the field of chemical drug synthesis, can solve problems such as limited application and poor compatibility, and achieve the effects of being suitable for large-scale industrial production, simple operation and mild conditions
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[0086] Concrete preparation method comprises the following steps:
[0087] Under an argon atmosphere, metal catalyst (5mol%) and ligand (10mol%) were successively added to the reactor, the reactor was sealed and solvent (1.0mL) was added with a syringe, followed by silicon hydrogen reagent (0.6mmol), the formula Alkyne compound 2 (0.45 mmol) represented by (II) and anthranilic anhydride compound 3 (0.3 mmol) represented by formula (III) were reacted at 40° C. for 16 hours. The end of the reaction was confirmed by thin-layer chromatography analysis, the reaction solution was washed with saturated sodium chloride aqueous solution, extracted with ethyl acetate, dried and filtered, and then concentrated into a dry powder with 400 mesh silica gel by rotary evaporation, and the reaction product was separated by column chromatography. 400-mesh silica gel 10g, the developer is petroleum ether and ethyl acetate with a volume ratio of 50:1 to 1:1, to obtain multi-substituted quinoline d...
Embodiment 1
[0089] The preparation of embodiment 1 compound 1a
[0090] 1a is called 2-phenylquinoline (1a), and its reaction formula is as follows:
[0091]
[0092] Under argon atmosphere, nickel bromide (5mol%) and 2,2-bipyridine (5mol%) were sequentially added to the reactor, the reactor was sealed and N,N-dimethylacetamide (DMA, 1.0 mL), followed by sequential addition of methyldiethoxysilane (0.6mmol), phenylacetylene 2a (0.45mmol), anthranilic anhydride 3a (0.3mmol), and reacted at 40°C for 16 hours. The end of the reaction was confirmed by thin-layer chromatography analysis, the reaction solution was washed with saturated sodium chloride aqueous solution, extracted with ethyl acetate, dried and filtered, and then concentrated into a dry powder with 400 mesh silica gel by rotary evaporation, and the reaction product was separated by column chromatography. 10 g of 400-mesh silica gel, and the developer is petroleum ether and ethyl acetate at a volume ratio of 50:1 to 5:1 to obta...
Embodiment 2
[0097] The preparation of embodiment 2 compound 1b
[0098] The full name of 1b is 2-(4-bromophenyl)quinoline (1b), and its reaction formula is as follows:
[0099]
[0100] Under argon atmosphere, nickel chloride (5mol%) and 2,2-bipyridine (5mol%) were sequentially added to the reactor, the reactor was sealed and N,N-dimethylacetamide (DMA, 1.0 mL), followed by adding triethylsilane (0.6mmol), 4-bromophenylacetylene 2b (0.45mmol), and anthranilic anhydride 3a (0.36mmol), and reacted at 40°C for 12 hours. The end of the reaction was confirmed by thin-layer chromatography analysis, the reaction solution was washed with saturated sodium chloride aqueous solution, extracted with ethyl acetate, dried and filtered, and then concentrated into a dry powder with 400 mesh silica gel by rotary evaporation, and the reaction product was separated by column chromatography. 400-mesh silica gel 10g, the developer is petroleum ether and ethyl acetate with a volume ratio of 50:1 to 5:1 to ...
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