2-Bromo-9,10-bis(2-naphthalenyl)anthracene

Yellow green powder

Synthesis of Compound 1092-Bromonaphthalene (11.0 g, 53.1 mmol) was dissolved in dry tetrahydrofuran (100 mL) under a nitrogen atmosphere at room temperature. The solution was cooled to -78° C. in a cooling bath, and t-butyllithium (47.0 mL, 1.7 pentane solution) was slowly added thereto. The mixture was stirred at the same temperature for about 1 hour, and Compound 104 (6.31 g, 22.0 mmol) was added thereto still at the same temperature. Then the cooling bath was removed, and the mixture was stirred at room temperature for about 3 hours. To the stirred mixture an aqueous ammonium chloride solution was added. The resulting mixture was extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was dissolved in diethyl ether, and then petroleum ether was added thereto. The mixture was agitated for several hours to obtain a solid compound. The solid was filtered and vacuum dried to obtain dinaphthyl dialcohol (11.2 g, 93percent). The dinaphtyl dialcohol (11.2 g, 20.5 mmol) was dispersed in 600 mL of acetic acid under a nitrogen atmosphere, to which potassium iodide (34.2 g, 206 mmol) and sodium hypophosphite hydrate (36.0 g, 340 mmol) were added. The resulting mixture was agitated while boiling for about 3 hours. After cooling to room temperature, the mixture was filtered and washed with water and methanol, and then vacuum dried to obtain Compound 109 (10.1 g, 96percent) a light yellow color.2-Bromonaphthalene (11.0 g, 53.1 mmol) was dissolved in dry tetrahydrofuran (100 mL) under a nitrogen atmosphere at room temperature. The solution was cooled to-78°C in a cooling bath, and t-butyllithium (47.0 mL, 1.7 pentane solution) was slowly added thereto. The mixture was stirred at the same temperature for about 1 hour, and Compound 104 (6.31 g, 22.0 mmol) was added thereto still at the same temperature. Then the cooling bath was removed, and the mixture was stirred at room temperature for about 3 hours. To the stirred mixture an aqueous ammonium chloride solution was added. The resulting mixture was extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was dissolved in diethyl ether, and then petroleum ether was added thereto. The mixture was agitated for several hours to obtain a solid compound. The solid was filtered and vacuum dried to obtain dinaphthyl dialcohol (11.2 g, 93percent). The dinaphtyl dialcohol (11.2 g, 20.5 mmol) was dispersed in 600 mL of acetic acid under a nitrogen atmosphere, to which potassium iodide (34.2 g, 206 mmol) and sodium hypophosphite hydrate (36.0 g, 340 mmol) were added. The resulting mixture was agitated while boiling for about 3 hours. After cooling to room temperature, the mixture was filtered and washed with water and methanol, and then vacuum dried to obtain Compound 109 (10.1 g, 96percent) a light yellow color.(Preparation of starting material represented by Chemical Formula i) A mixture of the diol (5.43 g, 10 mmol) obtained above, potassium iodide (15 g), and sodium hypophosphite hydrate (15 g) in acetic acid (100 ml) was stirred while refluxing for 1 hour under nitrogen. 2 opening having composite multi function cap 500 ml(7)(5.5g, 0.01mol), KI (6.3g, 0.04mol) NaH2-necked 500ml flask was charged with Compound (7) (5.5g, 0.01mol), KI (6.3g, 0.04mol) NaH2PO2 (6.3g, 0.07mol), 2 hr reflux insert as the AcOH (200ml) at 80 ~ 90oC under a nitrogen It was. Lower the temperature of the solid was washed with water and then filtered. Dissolve the solid in MC was extracted with distilled water and Methylene Chloride. After the extraction of the water japahjun Methylene Chloride layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a yellow solid. This solid was isolated using the method Column Chromatography yellow solid (8). (4.0g, 77percent)2-necked 500ml flask was charged with Compound (7) (5.5g, 0.01mol), KI (6.3g, 0.04mol) NaH2PO2 (6.3g, 0.07mol), 2 hr reflux insert as the AcOH (200ml) at 80~ 90oC under a nitrogen It was. Lower the temperature of the solid was washed with water and then filtered. Dissolve the solid in MC was extracted with distilled water and Methylene Chloride. After the extraction of the water Methylene Chloride layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a yellow solid. This solid was isolated using the method Column Chromatography yellow solid (8). (4.0g, 77percent)1-C. Production of compound Ic; [65] After the compound Ib (11.2 g, 20.5 mmol) was dispersed in an acetic acid (200 mL) in a nitrogen atmosphere, potassium iodide (34 g, 210 mmol) and sodium hy- pophosphite hydrate (37 g, 420 mmol) were added thereto and then boiled for 3 hours while agitation was performed. After cooling was performed at normal temperature, the resulting substance was filtered, washed with water and methanol, and subjected to vacuum drying to obtain a light yellow compound Ic (7.2 g, 64percent).[66] MS [M] = 509In an argon atmosphere, 11 g (21 mmol) of 2-bromo-9, 10-dinaphtyl-9, 9, 10, 10-tetrahydroanthracene-9, 10-dio 1 were dissolved into acetic acid, and 34 g (206 mmol) of potassium iodide and 36 g (340 mmol) of NaH3-1) While stirring a 250 ml round bottom flask, 21.60 g (0.042 mol) of compound (E-1) prepared in Synthesis 5-1 and 216 ml of THF were added.After the temperature was dropped to -78 C, 29.15 ml (0.047 mol) of n-BuLi was slowly added dropwise.After dropping, stir for 1 hour and 30 minutes, Triisopropyl borate14.62 g (0.064 mol) was added dropwise.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day.When the reaction is over, add 100 ml of 2N hydrochloric acid to make it acidic, After extracting with ethyl acetate and water, and removing water with MgSO4, Concentrated. The concentrated solution was recrystallized from hexane.As a result, 12.3 g (0.03 mol, yield 61.2%) of a white solid was obtained.Under N2 atmosphere, tetrakis (triphenylphosphine) palladium(80mg, 0.069mmol) was added to2, 4-diphenyl-6- (3- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1 , 3, 5-triazine (2.5g, 5.74mmol), 2-bromo-9, 10-bis (naphthalene-2-yl) anthracene (2.92g, 5.74mmol), In a toluene (50 mL) mixture of ethanol (6 mL) and an aqueous potassium carbonate solution (2M, 6 mL), The reaction was stirred at 90 C for 16 hours; after the reaction was completed, Distilled water was added to the reaction mixture to separate the toluene layer, and the aqueous layer was extracted with dichloromethane.The organic layer obtained after extraction was dried over anhydrous magnesium sulfate, and then filtered, Dichloromethane was distilled off under reduced pressure, and the obtained crude product was separated by column chromatography.The eluent used for the separation was a mixed solvent of petroleum ether and dichloromethane (3: 1v / v).A pale yellow solid (DiNaAN-m-TRZ) was obtained in a yield of 94% (4.0 g).9.4 g (48.0 mmol) acenaphthylen-5-ylboronic acid was dispersed in 100 mL of toluene, and under the protection of nitrogen, 8.5 g was added.(80.0 mmol) of anhydrous sodium carbonate, 20.4 g (40.0 mmol) of 5.0 g (17.7 mmol) of Int-13 prepared in the fourth step was dispersed in 60 mL of toluene, and 3.8 g (35.5 mmol) of anhydrous sodium carbonate was added under a nitrogen atmosphere. 7.5 g (14.7 mmol) of Under nitrogen protection, add in a four-neck bottle equipped with mechanical stirring, a thermometer, and a 1000 mL four-neck bottle of a condenser.Product 2-Bromo-9, 10-bis(2-naphthyl)anthracene (Compound M2) 45.8 g (0.09 mol, 1 eq), N-phenyl-4-(pyridin-3-yl)phenylamine (Compound N3) 24.4 g (0.099 mol, 1.1 eq), Pd2 (dba) 30.4 g (0.00045 mol, 0.5%), s-phos 0.4 g, 17.3 g of sodium tert-butoxide (0.18 mol, 2 eq), 500 mL of toluene, and the reaction mixture was refluxed for 6 h, and the reaction was monitored by TLC.After being cooled to room temperature, water and dichloromethane were added for extraction, the organic phase was concentrated, and the residue was subjected to column chromatography to give a solid product.Under the protection of nitrogen, 10.0 g (44.8 mmol) of Int-6 prepared in the second step, 19.0 g (37.3 mmol) of General procedure: A mixture of Compound 237-5 (8 g, 12.91 mmol), 2-bromo-4, 6-diphenylpyrimidine (4.82 g, 15.49 mmol), Pd(PPh3)4 (1.49 g, 1.29 mmol), K2CO3 (3.56 g, 25.82 mmol), and 1, 4-dioxane (150 ml)/H2O (30 ml) was stirred at 120 C. in a one-neck round bottom flask for 4 hours. The reactant was filtered at 110 C., and then washed with 1, 4-dioxane at 110 C. and with methanol to obtain Compound 237 (4.8 g) in the form of cotton wool, and the filtrate was separated with column chromatography (SiO2, Hexane:MC=3:1) to obtain powdery Compound 237 (8.2 g, 87%).

Molecular Weight:509.4
XLogP3:10.9
Rotatable Bond Count:2
Exact Mass:508.08266
Monoisotopic Mass:508.08266
Heavy Atom Count:35
Complexity:715
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes