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With triphenylphosphine; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 20 - 120℃; for 16h;
4 g of triphenylphosphine, 5.3 g of lithium chloride, 14 ml of tetramethyltin and 2.1 g of bis(triphenylphosphine)palladium(II) chloride are added to a solution of 6 g of <strong>[1070879-27-4]4-bromo-7-methoxyquinoline</strong> in 100 ml of DMF, under an inert atmosphere of argon at a temperature in the region of 20° C. The reaction medium is heated at a temperature in the region of 120° C. for 16 hours. After cooling, the insoluble material is filtered off. The filtrate is concentrated under reduced pressure. The residue obtained is taken up in 300 ml of EtOAc and 300 ml of water. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The oil obtained is taken up in 300 ml of EtOAc and 300 ml of water and then acidified with hydrochloric acid to pH 1. The aqueous phase is basified with sodium hydroxide to pH 10 and then extracted with 300 ml of EtOAc. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure to give 2.7 g of 4-methyl-7-methoxyquinoline, the characteristics of which product are as follows: 1H NMR spectrum (300 z, (CD3)2SO d6, delta in ppm): 2.65 (s: 3H); 3.94 (s: 3H); 7.23 (broad d, J=4.5 Hz: 1H); 7.28 (dd, J=9 and 3 Hz: 1H); 7.40 (d, J=3 Hz: 1H); 8.01 (d, J=9 Hz: 1H); 8.58 (d, J=4.5 Hz: 1H). Mass IE m/z=173 M+. base peak m/z=158 (M-CH3)+ m/z=143 (M-CH2O)+. m/z=130 (m/z=158-CO)+
General procedure: According to Scheme C,7-Methoxyquinolin-4-ol (1 eq) and POBr3 (10.4 eq.) Were placed in a round bottom flask,And the mixture was stirred for 3 hours. After completion of the reaction, the reaction solution was slowly added to the ice water and basified to pH 8 or more with ammonia water.The organic layer was extracted three times with ethyl acetate from the mixture of water and solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained mixture was subjected to column chromatography to give 4-bromo-7-methoxyquinoline. (1 eq.), 2-benzyl-4,4,5,5-tetramethyl-l, 3,2-dioxaborolane (1.2 eq.), Potassium carbonate (3 eq.), Tetrakis Phosphine) palladium (0) (0.05 eq.) Was stirred at 100 for 6 h under a solution of 1,4-dioxane and water in a ratio of 4: 1. After cooling to room temperature, the mixture was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate and filtered, and then concentrated under reduced pressure. Subsequently, a 4-benzylquinoline compound was obtained by column chromatography.
With phosphorus(V) oxybromide; at 110℃; for 3.0h;
22.74 g of 4-hydroxy-7-methoxyquinoline are added to 200 g of phosphorus oxybromide preheated to a temperature in the region of 110 C. The reaction medium is heated at this same temperature for 3 hours. The reaction medium is poured, while hot, into a mixture of 500 ml of EtOAc and 500 ml of ice-cold water. The medium is neutralized with potassium carbonate to pH 7. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, evaporated under reduced pressure and then purified by column chromatography (SiO2, EtOAc/cyclohexane 50/50 by volume as eluents, Ar), and 14.6 g of the expected product are obtained. [1475] 1H NMR spectrum (300 MHz, (CD3)2SO d6, delta in ppm): 3.97 (s: 3H); 7.43 (dd, J=9 and 3 Hz: 1H); 7.49 (d, J=3 Hz: 1H); 7.79 (d, J=4.5 Hz: 1H); 8.06 (d, J=9 Hz: 1H); 8.67 (d, J=4.5 Hz: 1H). [1476] Mass IE m/z=237 M+. base peak [1477] 4-Hydroxy-7-methoxyquinoline is prepared according to the process described in: J. Am. Chem. Soc., 68, 1268, 1946.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water;
General procedure: According to Scheme C,7-Methoxyquinolin-4-ol (1 eq) and POBr3 (10.4 eq.) Were placed in a round bottom flask,And the mixture was stirred for 3 hours. After completion of the reaction, the reaction solution was slowly added to the ice water and basified to pH 8 or more with ammonia water.The organic layer was extracted three times with ethyl acetate from the mixture of water and solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained mixture was subjected to column chromatography to give <strong>[1070879-27-4]4-bromo-7-methoxyquinoline</strong>. (1 eq.), 2-benzyl-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane (1.2 eq.), Potassium carbonate (3 eq.), Tetrakis Phosphine) palladium (0) (0.05 eq.) Was stirred at 100 C for 6 h under a solution of 1,4-dioxane and water in a ratio of 4: 1. After cooling to room temperature, the mixture was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate and filtered, and then concentrated under reduced pressure. Subsequently, a 4-benzylquinoline compound was obtained by column chromatography.
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