4-BROMO-4'-(DIPHENYLAMINO)BIPHENYL

4'-bromo-N, N-diphenyl-[l, l'-biphenyl]-4-amine (35): A mixture of (4-(diphenylamino)phenyl)boronic acid (1.5 g, 5.19 mmol), 4-iodo- 1 -bromobenzene (1.33 g, 4.71 mmol), NaA mixture of 4-diphenylaminophenyl boronic acid (2.57 g, 8.9 mmol), 4-bromo-iodobenzene (5.03 g, 17.8 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol) and K2C03 (3.0 g, 22 mmol) in dioxane/water (80 mE/i 5 mE) was degas sed and heated at about 80° C. for about 20 hours. The whole was mixed with water/dichloromethane, the organic phase was collected and washed with brine, dried over Na2SO4, loaded on silica gel, and purified by flash column (hexanes to hexanes/dichlo-romethane 30:1). The desired fraction was collected, and concentratedto give awhite solid (Compound 12), whichwas filtered and washed with methanol (2.70 g, in 76percent yield).Step 1: Synthesis of 4-(4-bromophenyl)-4'-phenyl-triphenylamine] [0550]A synthetic scheme of 4-(4-bromophenyl)-4'-phenyl-triphenylamine in Step 1 is shown in the following (M-I). [0551][0552]In a 500-mL three-neck flask, 22 g (70 mmol) of 4, 4'-dibromobiphenyl, 8.5 g(50 mmol) of diphenylamine, 1.9 g (10 mmol) of copper(I) iodide, 2.6 g (10 mmol) of 18-crown-6-ether, 6.9 g (50 mmol) of potassium carbonate, and 50 mL of l, 3-dimethyl-3, 4, 5, 6-tetrahydro-2(lH)pyrimidinone (abbreviation: DMPU) were put, and the mixture was stirred under a nitrogen atmosphere at 180 In a 500-mL three-neck flask, 22 g (70 mmol) of 4, 4'-dibromobiphenyl, 8.5 g(50 mmol) of diphenylamine, 1.9 g (10 mmol) of copper(I) iodide, 2.6 g (10 mmol) of 18-crown-6-ether, 6.9 g (50 mmol) of potassium carbonate, and 50 mL of l, 3-dimethyl-3, 4, 5, 6-tetrahydro-2(lH)-pyrimidinone (abbreviation: DMPU) were put, and the mixture was stirred under a nitrogen atmosphere at 180 Compound I-1 (12.5 g, 73.8 mmol), 4-bromo-4'-iodide (26.5 g, 73.8 mmol) were sequentially added to a round bottom flask.t-BuONa (10.7 g, 111 mmol), Pd(dppf)Cl2.CH2Cl2 (1.2 g, 1.47 mmol), and ultrasonically deoxygenated toluene (1.5 L) were refluxed under nitrogen atmosphere overnight. After cooling the reaction solution, ethyl acetate was used. Ester and water treatment, and the resulting organic layer was dried over MgSO 4Evaporate the solvent under reduced pressureThe crude product of compound II-1 was obtained.With silicone as the stationary phase, Dichloromethane/hexane as eluent, The crude product is subjected to column chromatography.Compound II-1 (23.0 g, 78percent) was obtained.Weigh 4-bromo-4'-iodobiphenyl(3.58g, 10.0mmol), diphenylamine (1.69g, 10.0mmol), copper powder (32.1mg, 0.5mmol) and potassium carbonate (1.54g, 11.2mmol) in a 250mL three-necked flask, add 100mL of o-dichlorobenzene as The solvent was vacuumed and filled with nitrogen for several times, and then stirred at room temperature for 10 minutes, then heated to 200 ° C, and refluxed for 24 hours. The reaction was monitored by TLC until the end.The reaction system is cooled to room temperature and then filtered to remove inorganic substances.The solvent was evaporated under reduced pressure, extracted with dichloromethane and dried over anhydrous sodium sulfate.Purification by column chromatography gave 2.32 g, yield 58percentDiphenylamine 15 g to a round bottom flask, 4-bromo-4'-iodo-1, 1'-biphenyl 47.7 g, t-BuONa 12.8 g, Pd2 (dba) 3 3.3 g, After dissolved (t-Bu) 3P 5.4 ml in 600 ml toluene was stirred in 50°C . Check the reaction by TLC and the reaction was terminated after addition of water.After purification the organic layer was extracted with EA and filtered under reduced pressure to give the intermediate column OP1-1 15.26 g (43percent yield).5.1g of diphenylamine, 10.8g of Intermediate 12, 3g of sodium tert-butoxide (manufactured by HIROSHIMA WAKO CO., LTD.), 0.5g of bis(triphenylphosphine) palladium (II) chloride (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.) and 500 mL of xylene were mixed under a flow of argon. The mixture was stirred at 130°C for 24 hours.After cooling, 1000 mL of water was added thereto, the mixture was celite-filtrated. The filtrate was extracted with toluene and then dried with anhydrous magnesium sulfate. This was condensed under reduced pressure, and the crude product obtained was purified using column chromatography. The purified matters were recrystallized with toluene, filtered out and dried to obtain 3.4g of pale yellow powder. The pale yellow powder was identified as Intermediate 13 by FD-MS analysis.General procedure: A mixture of compound 5 (0.307 g, 1 mmol), N, N-diphenyl-4-aminophenylboronic acid (0.289 g, 1 mmol), Pd(PPh

Molecular Weight:400.3
XLogP3:8.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:399.06226
Monoisotopic Mass:399.06226
Topological Polar Surface Area:3.2
Heavy Atom Count:26
Complexity:378
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes