(9-phenyl-9H-carbazol-2-yl)boronic acid

Under nitrogen atmosphere, intermediate C 3.22g (10mmol) was dissolved in 15ml anhydrous THF, cooled the reaction to -78°C, 2.5M n-BuLi 4ml was slowly added dropwise and then it was stirred at 0°C was for 1 hour. Thereafter, the temperature of the reaction was lowered to -78°C, trimethyl borate 12.47g (12mmol) was added dropwise and stirred at room temperature for 12 hours. After the reaction was completed into a 2N-HCl aqueous solution, extracted with ether, then stirred for 30 minutes. After completion of the reaction 2N-HCl aqueous solution was added, extracted with ether and stirred for 30 minutes. After removal of water the organic layer was filtered and concentrated under reduced pressure then it was dried over anhydrous MgSO4 , and purification by column chromatography using Hex: EA = 5: 1, to give intermediate D 2.27g (79percent).Nitrogen atmosphere, a 500 mL round bottom flask was charged with 2-bromo-N-phenyl-carbazole (19.8 g, 0.061 mol) dissolved in 200 mL of tetrahydrofuran at a temperature of -78 lowered and then 1.6M butyl lithium (45.6 mL , 0.073 mol) was added slowly and the.2 hours after stirring trimethylborate (13.6 mL, 0.122 mol) it was stirred at room temperature for 4 hours.When the reaction is finished, 2N hydrochloric acid into a 80 mL ethyl acetate and extracted using water, and then the organic layer was separated then concentrated and added to light treatment after the organic layer over anhydrous hexane yellowish crystals (N- phenyl-carbazol-2-boronic acid) to obtain a precipitate 12.6 g.(72percent).Preparation of compound 1-4 [102] After dissolving compound 1-3 (32 g, 85.96 mmol) in tetrahydrofurane (THF) (300 mL), 2.5 M n-BuLi in hexane (37.8 mL, 94.55 mmol) was added slowly to the reaction mixture in -78°C. After 1 hour, trimethylborate (12.4 mL, 111.7 mmol) was added. The reaction mixture was stirred for 12 hours, and distilled water was added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, was dried with MgSOAfter dissolving compound C-7-3 (28 g, 86.90 mmol) in THF (500 mL), n-BuLi (41.7 mL, 2.5 M) was added slowly to the mixture. After 1 hour, triisopropyl borate (30 mL, 130.3 mmol) was added to the mixture. After stirring the mixture for 12 hours at room temperature, distilled water was added to the mixture. Then, the mixture was extracted with EA, and then dried with MgSOSub 1-3-1 (6.4g, 20mmol) was dissolved in anhydrous Ether, lowering the temperature of the reaction to -78°C, n-BuLi (2.5M in hexane) (1.4g, 22mmol) was added dropwise slowly, and after, the reaction It was stirred for 30 minutes. After lowering the temperature of the reaction back to -78°C dropwise Triisopropyl borate (5.6g, 30mmol). Stirring at room temperature, diluted with water and it binds the 2N HCl. After completion of reaction, ethyl acetate and water, dried over MgSO4 and the organic layer was extracted and recrystallized silicagel column and the resulting organic material and then concentrated to a Sub 1-4-1 4.5g (yield: 78percent) was obtained.Preparation of compound 1-1 After dissolving 2-bromo-9-phenyl-9H-carbazole (25 g, 77.59 mmol) in tetrahydrofuran (THF) 400 mL in a flask, n-BuLi (2.5 M) was slowly added dropwise to the mixture at -78°C. After stirring the mixture for 1 hour, triisopropyl borate was added dropwise to the mixture. After completing the reaction, an organic layer was extracted with ethyl acetate, and the remaining moisture was removed using magnesium sulfate. The residue was dried using a rotary evaporator to obtain compound 1-1 (15.5 g, 70percent).After dissolving compound C-62-3 25 g (77.59 mmol) in THF 400 mL, n-buLi 37.2 mL (93.10 mmol) was slowly added to the mixture at -78°C. After 40 minutes, tnisopropyl borate 26.8 g (116.3 mmol) was added to the mixture. After heating the mixture slowly to room temperature, the mixture was stirred for 12 hours. Then, distilled water was added to the mixture, and the mixture was extracted with EA, dried with magnesium sulfate, and distilled under reduced pressure. Then, EA/Hex was added to the mixture, and the mixture was filtered under reduced pressure to obtain compound C-62-4 14 g (62.8 percent).Compound 1-3 (32g, 85.96mmol) was dissolved in THF 300mL and n-butyllithium (37.8mL, 94.55mmol, 2.5M in hexane) was slowly added at -78°C. 1 hour later, trimethylborate (12.4mL, 111.7mmol) was added. The mixture was stirred at room temperature for 12 hours, and then distilled water was added. The mixture was extracted with EA, dried with anhydrous MgSO[167] Compound 1-4 (20 g, 62.07 mmol) was dissolved in tetrahydofuran (THF) 200 mL, and n-buLi (29 mL, 74.48 mmol) in 2.5 M hexane was slowly added to the mixture at -78°C. After one hour, triisopropylborate (19.9 mL, 86.90 mmol) was added. After stirring the mixture at room temperature for 12 hours, distilled water was added and the mixture was extracted with ethyl acetate (EA). Then, the resulting product was dried with magnesium sulfate, and distilled under reduced pressure. The resulting product was recrystallized with ethyl acetate (EA) and hexane to obtain compound 1-5 (12 g, 41.79 mmol, 67.33 percent).Dissolve the intermediate C in anhydrous THF, cool down the temperature of the reaction to -78 , After the n-BuLi was added dropwise slowly, and the reaction was stirred for 1 hour at 0°C . Thereafter, the lower the temperature of the reaction to -78 added dropwise trimethyl borate, and stirred at room temperature for 12 hours after. After the reaction was completed into a 2N-HCl aqueous solution, extracted with ether, then stirred for 30 minutes. Removing water in the organic layer over anhydrous MgSO4 and then filtered under reduced pressure and purification of the compound produced by concentrating the organic solvent column Yes Blood and recrystallization to obtain the desired intermediate D (yield: 81percent).The experimental apparatus was thoroughly dried and 31.3 g of halogenated material was added to a 2L three-necked flask.Add 600ml of dried tetrahydrofuran, After dissolution, the temperature was lowered to -78C, and 44 ml of 2.5M n-BuLi was added dropwise.After stirring for one hour at the temperature, 13.4 g (1.3 eq.) of trimethyl borate was added dropwise at this temperature.After the addition was completed, the mixture was stirred at room temperature overnight.After the reaction is over, Add 4N hydrochloric acid solution, Extract with dichloromethane, The organic phase is washed to neutral with saturated saline solution.dry, Spin off the solvent, The resulting crude product is boiled with ethyl acetate, The filter cake is the boric acid product.18.1 g of intermediate b, yield 65percent.In a nitrogen atmosphere2, 5-dichlorobenzo[d]thiazole (10.0 g, 49.3mmol) and (The Compound 53-1 (6.2 g, 10 mmol), SM (starting material) (2.9 g, 10 mmol), Pd(PPh3)4 (0.6 g, 0.5 mmol), and K2C03 (4.1 g, 30 mmol) were dissolved into a mixed solution of toluene 200 ml and water 40 ml to form a mixture. Then, the mixture was heated and stirred while being refluxed for 12 hours. An organic layer was extracted with chloroform and washed with water. Water was removed from the organic layer with anhydrous magnesium sulfate and the organic layer was filtered. Then, an organic solvent was distilled away under a reduced pressure and removed from the organic layer and then was subjected to column purification, to obtain Compound 53 (7.0 g, yield:90%).In a nitrogen atmosphere, Compound A1 (20.0 g, 58.9 mmol) and (9-phenyl-9H-carbazol-2-yl) boronic acid (33.8 g, 117.7 mmol) were added to 300 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (48.8 g, 353.1 mmol) was dissolved in 100 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (4.1 g, 6 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 2-1 (30.2 g, 77%) through ethanol recrystallization.In a nitrogen atmosphere, 4-bromo-9H-carbazole (30.0 g, 122.5 mmol) and (9-phenyl-9H-carbazol-2-yl) boronic acid (35.2 g, 122.5 mmol) were added to 300 ml of tetrahydrofuran and stirred and It was refluxed. Thereafter, potassium carbonate (33.9 g, 244.9 mmol) was dissolved in 100 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (4.2 g, 3 mol%) was added thereto. After 4 hours the reaction was lowered to room temperature and filtered. The filtrate was dissolved in chloroform and extracted with water, and then the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was dried, and then compound sub 4 (31.5 g, 63%) was prepared through ethyl acetate recrystallization.S1. In a 250 mL reaction flask, add 2, 7-dibromo-9-phenyl-9H-carbazole (12.03 g, 30 mmol),

Molecular Weight:287.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:287.1117589
Monoisotopic Mass:287.1117589
Topological Polar Surface Area:45.4
Heavy Atom Count:22
Complexity:385
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes