A kind of preparation method of isoquinoline derivative
An isoquinoline and compound technology, applied in the field of organic chemical synthesis, can solve the problems of low yield, expensive and rare reagents, complicated process and the like, and achieves the effects of high yield, simple operation and simple reaction
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Embodiment 1
[0066] Embodiment 1: the synthesis of 1,3-two m-tolylisoquinolines
[0067]
[0068] Add 100ml of water, 20mmol o-cyanophenylacetonitrile, 40mmol potassium m-tolyl trifluoroborate, 0.4mmol palladium acetylacetonate, 0.8mmol nitrogen-containing ligand L-1 and 100mmol p-toluenesulfonic acid monohydrate in the reaction vessel, The reaction was carried out under stirring at 60° C. for 30 hours. After the reaction was over, the mixture was poured into ethyl acetate, followed by saturated NaHCO 3 aqueous solution and brine washing, after the aqueous layer was extracted with ethyl acetate, the organic layer was combined (that is, the organic layer after the combined washing and the organic layer obtained by extraction) were washed with anhydrous Na 2 SO 4 After drying, the solvent was evaporated under negative pressure, and the residue was purified by flash column chromatography (n-hexane / ethyl acetate, the volume ratio of the two was 1:1) to obtain the target product as a liqui...
Embodiment 2
[0070] Embodiment 2: the synthesis of 1,3-two p-chlorophenylisoquinolines
[0071]
[0072] Add 100ml of water, 20mmol of o-cyanophenylacetonitrile, 60mmol of potassium p-chlorophenyltrifluoroborate, 1mmol of palladium acetylacetonate, 3mmol of nitrogen-containing ligand L-1 and 200mmol of p-toluenesulfonic acid monohydrate in the reaction vessel, at 80 °C under stirring for 20 hours. After the reaction was over, the mixture was poured into ethyl acetate, followed by saturated NaHCO 3 aqueous solution and brine washing, after the aqueous layer was extracted with ethyl acetate, the organic layer was combined (that is, the organic layer after the combined washing and the organic layer obtained by extraction) were washed with anhydrous Na 2 SO 4 After drying, the solvent was evaporated under negative pressure, and the residue was purified by flash column chromatography (n-hexane / ethyl acetate, the volume ratio of the two was 1:2) to obtain the target product as a solid. Yie...
Embodiment 3
[0075] Embodiment 3: the synthesis of 1,3-diphenyl-4-ylisoquinoline
[0076]
[0077] Add 100ml of water, 20mmol o-cyanophenylacetonitrile, 80mmol potassium p-phenylphenyltrifluoroborate, 2mmol palladium acetylacetonate, 5mmol nitrogen-containing ligand L-1 and 300mmol p-toluenesulfonic acid monohydrate in the reaction vessel, React at 140°C for 15 hours with stirring. After the reaction was over, the mixture was poured into ethyl acetate, followed by saturated NaHCO 3 aqueous solution and brine washing, after the aqueous layer was extracted with ethyl acetate, the organic layer was combined (that is, the organic layer after the combined washing and the organic layer obtained by extraction) were washed with anhydrous Na 2 SO 4 After drying, the solvent was evaporated under negative pressure, and the residue was purified by flash column chromatography (n-hexane / ethyl acetate, the volume ratio of the two was 1:3) to obtain the target product. Yield 69.7%, purity 98.6% (HPL...
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