3-Biphenylboronic acid pinacol ester

Synthesis of Intermediate I-8 3-bromo-1, 1′-biphenyl (20 g, 85.8 mmol) was dissolved in dimethylforamide (DMF) (1 L) under a nitrogen environment, bis(pinacolato)diboron (26 g, 103 mmol), (1, 1′-bis(diphenylphosphine)ferrocene)dichloropalladium(II) (0.7 g, 0.85 mmol), and potassium acetate (58 g, 595 mmol) were added thereto, and the mixture was heated and refluxed at 150° C. for 5 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven. The obtained residue was separated and purified through flash column chromatography to obtain Compound I-8 (20 g and 85percent). HRMS (70 eV, EI+): m/z calcd for CThe compound (2) of the present invention can be synthesized by the following method.1) In a 500ml three-neck bottle, Add 2, 7-dibromo-9H-carbazole(32.50g, 100mmol), [1, 1:4, 1-terphenyl]-4-borate(35.60g, 100mmol), Potassium carbonate (27.64 g, 200 mmol), 150 g of toluene, 75 g of ethanol, 75 g of water, adding tetrakis(triphenylphosphine)palladium under N2 protection, After reacting at 85 C for 12 h, the reaction was completed by TLC and the temperature was lowered.After the temperature was lowered to room temperature, [1, 1'-biphenyl]-3-borate (29.62 g, 100 mmol) was added to a three-necked flask, and reacted at 85 C for 12 h, and the reaction was confirmed by TLC.After cooling to room temperature, the reaction solution was washed twice with water (200 ml).The organic phase is obtained by liquid separation, and decolorization by adding activated carbon.Filtration, distilling off the solvent under reduced pressure, and then recrystallizing twice with ethyl acetate.Drying under vacuum gave the intermediate 2-([1, 1'-biphenyl]-3-yl)-7-([1, 1:4, 1-terphenyl]-4-yl)-9H- Carbazole.1) In a 500ml three-neck bottle, Add 3, 5-dibromo-9H-carbazole (32.50 g, 100 mmol), 3-(naphthalen-2-yl(phenyl)amino)phenyl boronate (42.14 g, 100 mmol), Potassium carbonate (27.64 g, 200 mmol), 150 g of toluene, 75 g of ethanol, 75 g of water, adding tetrakis(triphenylphosphine)palladium under N2 protection, After reacting at 85 C for 12 h, the reaction was completed by TLC.Start to cool down. After falling to room temperature, [1, 1'-Diphenyl]-4-boronate (28.02 g, 100 mmol) was added to a three-necked flask, and reacted at 85 C for 12 h, and the reaction was confirmed by TLC. After cooling to room temperature, The reaction solution was washed twice with water (200 ml), and the organic layer was separated.Adding activated carbon to decolorize, filtering, and distilling off the solvent under reduced pressure.Recrystallized twice with ethyl acetate, Drying under vacuum gave the intermediate N-(4-(5-([1, 1'-biphenyl]-3-yl)-9H-indazol-3-yl)phenyl)-N-phenylnaphthalene- 1-amine2)In a 250ml three-neck bottle, add(4R, 8S)-2, 6-dibromo-4, 8-di(indol-4-yl)benzo[1, 2-b:4, 5-b']dithiophene(7.52g, 10mmol)[1, 1'-biphenyl]-3-borate(5.88g, 21mmol), 100 g of toluene, palladium acetate was added under the protection of N2, and reacted at 120 C for 12 h.The TLC monitoring reaction was completed. After cooling to room temperature, the reaction solution was washed with water (200 ml)Two times, the organic phase was separated by liquid separation, decolorized by adding activated carbon, filtered, and the solvent was distilled off under reduced pressure, and then recrystallized twice with ethyl acetate.Drying under vacuum gave the compound (30) 7.55 g, The yield was 84%.

suzuki reaction

Molecular Weight:280.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:280.1634601
Monoisotopic Mass:280.1634601
Topological Polar Surface Area:18.5
Heavy Atom Count:21
Complexity:344
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes