* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24 h; Inert atmosphere; Reflux
Round bottom flask was charged with 9-Phenyl-9H-carbazole-3-boronic acid 15g (52.25mmol), 4-chloro-Phenylboronicacid8.98g (57.47mmol) and the mixture of toluene (174ml) and the mixture was then dissolved in 21.66g of potassium carbonate (156.74 mmol) was added to a stirred aqueous solution of dissolved 87ml. Followed by adding thereto tetrakis triphenylphosphine palladium 1.20g (1.04mmol) was stirred and refluxed for 24 hours under a nitrogen atmosphere. After the end of the reaction the extract was concentrated to dryness and extracted with ethyl acetate and filtered through a magnesium sulfate, and the filtrate under reduced pressure. The product n- hexane / dichloromethane (6: 4 by volume) was purified by a silica gel column chromatography to give the intermediate (I) as 16.13g (85percent yield).
85%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24 h; Inert atmosphere; Reflux
Round bottom flask was charged with 9-Phenyl-9H-carbazole-3-boronic acid 15g (52.25mmol), 4-chloro-Phenylboronicacid 8.98g dissolved in an aqueous solution of potassium carbonate 21.66g (156.74mmol) was dissolved was added to (57.47mmol) in toluene (174ml) into theIt was added to 87ml and stirred. Here tetrakistriphenylphosphine palladium was added to 1.20g (1.04mmol) of nitrogen atmosphere It was stirred under reflux for 24 hours under a group. After completion of the reaction, magnesium sulfate, the extract was then extracted with ethyl acetateIt was dried, filtered and concentrated under reduced pressure to the filtrate. Silica gel with: a product n- hexane / dichloromethane (volume ratio 4 6)The desired compound was purified by column chromatography of the intermediate (I) to give a 16.13g (85percent yield).
Reference：
[1] Patent: KR2016/12846, 2016, A, . Location in patent: Paragraph 0207; 0208; 0209
[2] Patent: KR2016/22081, 2016, A, . Location in patent: Paragraph 0454; 0455; 0456; 0457
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Inert atmosphere; Heating;
In a three-necked flask equipped with a stirrer 2.50 g (6.23 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong> (compound a), 1.79 g (6.23 mmol) of 9-phenylcarbazole-3-boronic acid (compound b), 41.6 ml of 2 M potassium carbonate (K2CO3) aqueous solution (83.2 mmol of potassium carbonate) and 125 ml of tetrahydrofuran (THF) were added and nitrogen bubbling was carried out for 1 hour. 350 mg (0.31 mmol) of tetrakis (triphenylphosphine)palladium (Pd (PPh 3) 4) was added thereto and heated and stirred overnight. The reaction solution was returned to room temperature and the solvent was distilled off. After adding dichloromethane to the residue and redissolving it, and then washed with a saturated saline solution. Anhydrous magnesium sulfate was added to the organic layer, and the organic layer was dried and filtered. After concentrating the filtrate, silica gel column chromatography (dichloromethane: hexane = 1: 4) was carried out, a target compound c was obtained in a yield of 1.32 g (0.24 mmol) in a yield of 38percent.
32%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 16h;Inert atmosphere;
100 g (348 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid was dissolved in 1.3 L of tetrahydrofuran (THF) in a nitrogen environment, 168 g (418 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong> and 4.02 g, 3.48 mmol) of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was agitated. 102 g (696 mmol) of potassium carbonate saturated in water was added thereto, and the mixture was heated and refluxed at 80 °C for 16 hours. When the reaction was terminated, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and treated with anhydrous MgSO4 to remove moisture and then, filtered and concentrated under a reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound I-28 (62.8 g, 32 percent). HRMS (70 eV, EI+): m/z calcd for C36H23BrN2: 562.1045, found: 562.1. Elemental Analysis: C, 77 percent; H, 4 percent
(3-(8-bromodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Reflux;
10g (35 mmol) of the compound (9-phenyl-9H-carbazol-3-yl) boronic acid and 11.3 g (35 mmol) of 2,8-dibromodibenzo [b, d] furan were mixed and dissolved in 90 mL of tetrahydrofuran , And a solution prepared by dissolving 14.5 g (105 mmol) of potassium carbonate in 30 mL of water was added and warmed. 400 mg (0.35 mmol) of tetrakis- (triphenylphosphine) palladium was added to the refluxed mixture, and the mixture was refluxed and stirred for 12 hours. When the reaction is completed, the solvent is removed, and while cooling to room temperature, ethyl acetate is added to slurry. This was filtered and washed with water and ethanol successively to obtain 12.4 g (yield: 73percent) of a white compound H.
65%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 16.5h;Inert atmosphere;
Example 1.13.17 3-(8-bromodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole (Compound 17) A mixture of (9-phenyl-9H-carbazol-3-yl)boronic acid (1.50 g, 5.22 mmol), <strong>[10016-52-1]2,8-dibromodibenzo[b,d]furan</strong> (2.98 g, 9.14 mmol), tetrakis(triphenylphosphine) palladium(0) (0.30 g, 0.26 mmol), potassium carbonate (2.17 g, 15.67 mmol), 1,4-dioxane (50.00 mL), and water (10.00 mL) was degassed with bubbling argon for 30 min. The reaction mixture was then heated to 80° C. and was stirred overnight (16.5 hours), maintaining an argon atmosphere. Consumption of the starting material was confirmed by thin-layer chromatography and the reaction was cooled to room temperature. The product was extracted with dichloromethane, dried, and purified by silica gel column chromatography with dichloromethane in hexanes as the eluent. The product fractions were then dried and the product was collected to yield Compound 17 (1.65 g, 65percent). Confirmed by LCMS (APCI): calculated for C30H18BrNO (M+H): 488. Found: 488.
61%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; for 15h;Inert atmosphere; Reflux;
Under argon or nitrogen atmosphere at 65.2 g (200 mM)2,8-Dibromodibenzo[b,d]furan, 60.3 g (210 mM)(9-Phenyl-9H-carbazol-3-yl)boronic acid,4.7 g (4 mM) of tetrakis(triphenylphosphine)palladium(0)600 ml of toluene and 300 ml of a 2M Na2CO3 aqueous solution were added and the mixture was heated while refluxing for 15 hours.After completion of the reaction, extraction was performed using dichloromethane and placed in MgSO 4 for filtration.After removing the solvent of the filtered organic layer, purification was performed by column chromatography to obtain 58.7 g of Intermediate I-1(3-(8-Bromodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole) (yield 61percent)
The Bl (3.34g, 10 mmol) was added vial, the injection of THF dried, placed in a dry ice - acetone bath cooling, -78 ° C was added dropwise n-BuLi (1 lmmol, 2.5M) solution, stirring was continued for 3 hours and then triisopropyl borate (2.07g, 11 mmol) added to the bottle, slowly brought to room temperature and stirred overnight. After completion of the reaction, dilute HC1 solution was dropwise jerk, and extracted with methylene chloride, the organic layer was dried, solvent was removed, dichloromethane and petroleum ether (60-90) was washed with a mixture of beating to give D-1 (2.57g, y = 86percent),
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
