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With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 75 - 80℃; for 4h; Inert atmosphere;
3 Synthesis of compound 3:
9-bromophenanthrene (30 g, 116.67 mmol),4’-chlorobiphenyl-4-boronic acid (27.12g, 116.67mmol),Tetrakis (triphenylphosphine) palladium (7.45g, 6.45mmol),Potassium carbonate (35.67g, 258.09mmol),Tetrabutylammonium chloride (1.47g, 6.45mmol),Toluene (240ml),Ethanol (120ml) and deionized water (36ml) were added to a three-necked flask. NitrogenThe temperature was raised to 75 ° C to 80 ° C under gas protection, and the mixture was heated under reflux and stirred for 4h.After the reaction was completed, the solution was cooled to room temperature, and dichloromethane and water were added to extract the reaction solution.The organic phases were combined, dried over anhydrous magnesium sulfate, filtered to obtain a filtrate, and concentrated;The crude product was purified by silica gel column chromatography.Intermediate-D-1 (29.79 g, yield 70%) was obtained.
79%
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water Inert atmosphere;
2-34
Compound 2-A (15 g, 58.3 mmol) and Compound 2-D (14.9 g, 64.2 mmol) were added to 300 ml of THE under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, potassium carbonate (16.1 g, 116.7 mmol) was dissolved in 48 ml of water, added thereto, and the mixture was sufficiently stirred and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.2 mmol) was added. After 10-hour reaction, the reaction mixture was cooled to room temperature, and the organic layer and the aqueous layer were separated, and then the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to give 16.8 g of Compound sub2-A-3. (Yield: 79%, MS: [M+H]+=365)
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 4h; Inert atmosphere;
2 Synthesis of Sub2
2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (10.0 g, 27.95 mmol) under a nitrogen stream, (4'-chloro-[1,1'-biphenyl]-4-yl)boronic acid (6.50 g, 27.95 mmol), Pd(PPh3)4 (0.97 g, 0.84 mmol),K2CO3 (11.59 g, 83.35 mmol), 200 ml of 1,4-dioxane and 50 ml of H2O were mixed and stirred at 100 °C for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent of the filtered organic layer, 11.4 g (yield: 80%) of the target compound was obtained by column chromatography.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 7.5h; Inert atmosphere; Reflux;
27 Preparation of c-359:
Combine c-207 (56.14mmol, 13.48g), δ-359 (55.04mmol, 12.80g), Pd(PPh3)4 (1.10mmol, 1.27g), K2CO3 (110.08mmol, 15.21g), 150mL toluene, 50mL ethanol , 50mL of water, placed in a reaction flask, under the protection of nitrogen, stirring and heating to reflux for 7.5 hours; after full reaction, cooled to room temperature, vacuum filtration to obtain the crude product, then rinse the crude product with ethanol, and finally use toluene/ethanol=5: 1. Recrystallize to obtain c-359 (15.70g, yield 82%); HPLC purity ≥99.67%
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