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With tetrakis(triphenylphosphine)palladium (0); In ethanol; toluene;
Example 6 Synthesis of Carbazole Derivative 6 Toluene (80 mL), ethanol (20 mL) and 2M sodium carbonate aqueous solution (40 g) were added to a mixture of 2,7-dibromocarbazole (6.50 g), phenylboronic acid (7.32 g) and tetrakistriphenylphosphine palladium (0.734 g), followed by refluxing under nitrogen flow for 3 hours. The resultant mixture was left to cool to room temperature. Then, the insoluble matter was filtrated and the solvent was evaporated, to thereby obtain 4.15 g of 2,7-diphenylcarbazole as pale brown powder.
2,7-diphenyl-N-[4-(8-hydroxyoctyloxyphenyl)]carbazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2.0 g
With copper; potassium carbonate; In nitrobenzene; for 7h;Inert atmosphere; Reflux;
The obtained <strong>[42448-04-4]2,7-diphenylcarbazole</strong> (4.01 g), 4-(8-hydroxyoctyloxy)iodobenzene (4.37 g), potassium carbonate (3.45 g), copper powder (0.5 g) and nitrobenzene (20 mL) were refluxed under nitrogen flow for 7 hours. The resultant mixture was left to cool to room temperature. The insoluble matter was filtrated and the solvent was evaporated. The resultant product was chromatographically treated (silica gel, eluent: 10% ethyl acetate/toluene), to thereby obtain 2.0 g of 2,7-diphenyl-N-[4-(8-hydroxyoctyloxyphenyl)]carbazole as pale brown oily matter.
2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine[ No CAS ]
C45H30N4[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
55%
With potassium phosphate; In N,N-dimethyl-formamide; at 160℃; for 12h;
<strong>[42448-04-4]2,7-diphenyl-9H-carbazole</strong> (1 eq), 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine (1 eq), and K3PO4 (2 eq) were dissolved in DMF and stirred at about 160 degrees Celsius for about 12 hours. After cooling, an aqueous NaCl solution was poured thereto to quench the reaction, followed by stirring for about 30 minutes. The precipitate thus obtained was filtered, and the solid thus obtained was extracted with distilled water and DCM, dried with MgSO4, and dried under a reduced pressure. The organic layer thus obtained was separated by column chromatography (MC/Hex) to produce Compound 4 (yield: 55%). C45H30N4: M+1 626.74
With caesium carbonate; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;
Prepare a 100mL dry two-necked round bottom flask, intermediate (4) (2mmol), intermediate (5) (1mmol),CsCO3 (2.5mmol) was added to the flask, connected to the condenser, degassed and introduced nitrogen, repeated three times.Dry DMF (50 mL) was added and refluxed for 24 h under nitrogen. After the reaction solution was cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by a silica gel chromatographic column to obtain a white solid, namely compound 22-1, with an HPLC purity of 99.8% and a yield: 86%.
With caesium carbonate; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;
Prepare a 100mL dry two-necked round bottom flask, intermediate (70-1) (1mmol), intermediate (4) (1mmol),CsCO3 (1.1 mmol) was added to the flask, connected to the condenser, degassed and introduced nitrogen, repeated three times.Dry DMF (50 mL) was added and refluxed for 24 h under nitrogen. After the reaction solution was cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by a silica gel chromatography column to obtain a white solid, namely compound 70-2, with an HPLC purity of 99.0%, and a yield: 41%.
With Palladium(0) bis(dibenzylideneacetone); sodium tertiary butoxide; dicyclohexyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 20h; Inert atmosphere;
16 2) Synthesis of Compound 184
General procedure: To a reaction vessel were added 184-1, 47.2 g (100mmol) of the compound 184-C, 36.9 g (110mmol), 26.9 g (240mmol) of potassium tert-butoxide, 575 mg (1 mmol) of palladium bis-dibenzylideneacetone, 953 mg (2mmol) of 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl and 1000mL of xylene (xylene) under an argon atmosphere, and the mixture was stirred at 140°C for 20 hours. The reaction mixture was cooled to room temperature, 1000ml of water were added, filtered, the filter cake washed with copious amounts of water, dried in vacuo and the crude product purified by column chromatography on silica gel (eluent: ethyl acetate/hexane) to give 57.8 g of compound 184 in 75% yield with 99.9% HPLC purity.
With Palladium(0) bis(dibenzylideneacetone); sodium tertiary butoxide; tri-tert-butylphosphonium hydrogen tetrafluoroborate In toluene at 80℃; for 2h; Inert atmosphere;
2.1 (1) Synthesis of Compound D
Under an Ar atmosphere, Compound A (197 mmol), 2,7-diphenyl-9H-carbazole (414 mmol), Pd(dba)2 (9.85 mmol), P(t-Bu)3HBF4 (9.85 mmol), and tBuONa (689 mmol) were added to 700 ml of toluene, and heated and stirred at about 80° C. for about 2 hours. Water was added thereto, filtering with celite was performed, liquid layers were separated, and an organic layer was concentrated. The crude product was separated by silica gel column chromatography to obtain Compound D (yield 88%). Through FAB MS measurement, Compound D was identified (M/Z=749.6).
With caesium carbonate In N,N-dimethyl acetamide at 120℃; Inert atmosphere;
5.1 1) Synthesis of compound IM-10
Under an argon (Ar) atmosphere, 2,7-diphenyl-9H-carbazole (20.00 g, 62.62 mmol), Cs2CO3 (40.80 g, 2.0 equiv, 125.2 mmol), DMA (65 mL) and 1-bromo-2-fluorobenzene (21.92 g, 2.0 equiv, 125.2 mmol), then heated to about 120° C. and stirred. After cooling to room temperature in air, water and toluene were added to the reaction mixture, and the organic layer was taken separately. The extracted organic layer was washed with brine solution and dried over MgSO4. MgSO4 was filtered, and the organic layer was concentrated. The crude product thus obtained was purified to obtain compound IM-10 (20.70 g, yield 70%).
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