Sulfuric Acid → 2-[6-Methoxy-4-(5,6,6'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-yloxymethyl]-propane-1,3-diol

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Reaction Steps

6-Methoxy-4-(5,6,6′-trimethyl-[2,2′]bipyridin-3-yloxy)-quinolin-7-ol (compound 443) (75 mg) was dissolved in tetrahydrofuran (2 ml) to prepare a solution. Triphenylphosphine (102 mg), (2,2-dimethyl-[1,3]dioxan-5-yl)-methanol (34 mg), and diethylazodicarboxylate (0.07 ml) were added to the solution, and the mixture was stirred at room temperature for 7 hr. Further, 1N-sulfuric acid (4 ml) was added to the reaction solution, and the mixture was stirred at room temperature overnight. The reaction solution was brought to 0° C., was stirred, and was made alkaline by the addition of a 10% aqueous sodium hydroxide solution. Water was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (56 mg, yield 62%).

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