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With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 12h;Inert atmosphere;
(3) Synthesis of Compound d-6; A nitrogen atmosphere was established in a 200-ml three-necked flask. After that, the following reagents and solvents were loaded into the flask.Compound d-4: 7.08 g (20.0 mmol)Compound d-5: 5.46 g (22.0 mmol)Sodium carbonate: 10.6 g (100 mmol)Toluene: 100 mlEthanol: 20 mlWater: 100 ml[0096] Next, the reaction solution was stirred at roomtemperature under a nitrogen atmosphere, and to the stirred solution were added 1.16 g of tetrakis (triphenylphosphine) palladium ( 0 ) . Next, the reaction solution was warmed to a temperature of 80 C and stirred at the same temperature (80C) for 12 hours. After the completion of the reaction, the organic layer was extracted with toluene, and the resultant organic layer was dried over anhydrous sodium sulfate. The organic layer was then concentrated under reduced pressure to give a crude product. Next, the resultant crude product was purified by silica gel columnchromatography (developing solvent: toluene-ethyl acetate mixed solvent) to afford 4.92 g of Compound d-6 as a white solid (yield: 62%).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 8h;Inert atmosphere;
4 -phenoxathiinyl boronic acid 18.8g (76.88mmol),methyl-2-bromo-5-chloro-benzoate 21.1g (84.57mmol) and tetrakis triphenylphosphinepalladium0.89g (0.769mmol) were placed in a flask, and under a nitrogen atmosphere, itwas dissolved in tetrahydrofuran 257 ml, and then an aqueous solution 128ml of dissolvedpotassium carbonate 17g (115.3mmol) was added, and stirred at reflux at 70 C for 8 h. After completion of the reaction, it was extracted with ethyl acetate,the extract was dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gelcolumn chromatography using n- hexane / ethyl acetate (9: 1 volume ratio) to obtain intermediate M-3 of the desired compound 26.1 g (92% yield).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h;Inert atmosphere;
In a nitrogen atmosphere, 100 g (282 mmol) of the compound I-1 was dissolved in 900 mL of tetrahydrofuran (THF), and thereto was added methyl 2-(77.4 g, 310 mmol) of methyl 2-bromo-5-chlorobenzoate and tetrakis (triphenylphosphine) palladium3.26 g (2.82 mmol) of tetrakis (triphenylphosphine) palladium was added thereto and stirred. Saturated potassium carbonate in water97.4 g (705 mmol) of nate were added, and the mixture was refluxed by heating at 80 DEG C for 21 hours. After completion of the reaction, water is added to the reaction solutionThe reaction mixture was extracted with dichloromethane (DCM), then dried over anhydrous MgSO 4, filtered, and concentrated under reduced pressure. Get thisThe residue was purified by flash column chromatography to obtain 112 g (94%) of compound I-5.
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