N-[1,1'-biphenyl]-4-yl-N-(4-broMophenyl)-9,9-diMethyl-9H-Fluoren-2-aMine

A mixture of N-([1, 1'-biphenyl]-4-yl)-9, 9-dimethyl-9H-fluoren-2-mine (1.00 g, 2.77 mmol), 1-bromo-4-iodobenzene (1.00 g, 3, 53 mmol), potassium hydroxide (0.30 g, 5.38 mmol), coprous iodide (5.70mg, 0.03 mmol) and 1, 10-Phenanthroline monohydrate (5.40 mg, 0.03 mmol) in ortho-xylene (30 mL) was stirred at 150 °C for 8 h under nitrogen atmosphere. After cooling to room temperature, the solution was evaporated in vacuum. The cold water was added to the mixture and finally extracted with DCM. The combined organic phase was collected, filtered and dried over MgSOCompound I-11 (26.7 g, 73.8 mmol) was sequentially added to a round bottom flask.Compound II-11 (20.9 g, 73.8 mmol), t-BuONa (10.7 g, 111 mmol), Pd(OAc)2 (0.33 g, 1.47 mmol), and ultrasonically deoxygenated toluene (1.5 L), After refluxing under nitrogen, the reaction solution was cooled and treated with ethyl acetate and water.The resulting organic layer was dried over MgSO4.The solvent was distilled off under reduced pressure to give the crude compound III-11.Silica gel as stationary phase, dichloromethane/hexane as eluent, The crude product was subjected to column chromatography to give compound III-11 (29.7 g, 78percent).Example 2710.8 g (30.0 mmol) of compound I-1, 5.64 g (20.0 mmol) of 4-bromo-1-iodobenzene, 0.36 g (0.4 mmol) of PdSynthesis method of compound A-14; Synthesis method of intermediate a; N-(biphenyl-4-yl)-9, 9-dimethyl-9H-fluoren-2-amine, 1-Bromo-4-iodobenzene, PdBiphenyl-4-yl-(4-bromophenyl)-(9, 9-dimethyl-9H-fluoren-2-yl)amineTo a round bottom flask was added 10 g of N-([1, 1'-biphenyl]-4-yl)-9, 9-dimethyl-9H-fluoren-2-amine, 11.0 g of 1-bromo-4-iodobenzene, 4.0 g of t-BuONa, 1.0 g of Pd2(dba)3 and 1.6 ml of (t-Bu)3P were dissolved in 200 ml of toluene, and the mixture was stirred at 50°C. After the reaction was confirmed by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 6.72 g (yield 47percent) of OP11, 4-dibromobenzene (2.4 g, 0.010 mol) in N-(biphenyl-4-yl) -9, 9-dimethyl-9H-fluoren-2-amine (3.6 g, 0.010 mol), Pd(dba)2 ( 0.5 g, 0.0005 mol), sodium-tert-butoxide (1.9 g, 0.020 mol) in 70 mL TOL into a 95°C, 4 hours reaction was stirred. After completion of the reaction H 2 0: after the delamination MC column purification (n-HEXANE: MC) to afford 4.1 g of Intermediate 1-1 (79percent). (M / z = 516)General procedure: Intermediates 1-1 (5.0 g, 0.018 mol), 4-bromo-N, N-dip-tolylaniline (12.5 g, 0.036 mol), Pd(dba)A mixture of 1, 4-dibromobenzene(0.2 g, 0.8 mmol), 2-(4-biphenylyl)amino-9, 9-dimethylfluorene (0.36 g, 1 mmol), Pd(OAc)2 (0.046 g, 0.2 mmol), P(t-Bu)3 (0.04 g, 0.2 mmol), and Cs2CO3 (1.63 g, 5 mmol) in drytoluene (15 mL) was stirred and heated at 110° C overnight. After the mixture was cooled to room temperature, saturated ammonium chloride solution was added to the reaction solution. The solution was extracted with dichloromethane, dried with MgSO4, and subjected to column chromatography (silica gel, dichloromethane/hexanes = 3:1). A yellow solid was obtained with the following properties: yield, 57percent (0.24 g); mp 160.1–161.5° C; 1HNMR [400 MHz, (CD3)2CO]: δ 7.64 (d, 1H, J = 8 Hz), 7.60–7.57 (m, 3H), 7.50–7.48 (m, 2H), 7.43-7.40 (m, 2H), 7.38–7.26 (m, 5H), 7.25(s, 1H), 7.20 (s, 1H), 7.17 (s, 1H), 7.15 (s, 1H), 7.06–7.02 (m, 3H), 1.42 (s, 6H). HRMS: m/z calcd. for C33 H26 Br N: 516.1321 [M-H];Found: 516.1337.

Molecular Weight:516.5
XLogP3:10
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:515.12486
Monoisotopic Mass:515.12486
Topological Polar Surface Area:3.2
Heavy Atom Count:35
Complexity:681
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes