Home Cart Sign in  
Chemical Structure| 1082549-89-0 Chemical Structure| 1082549-89-0

Structure of 1082549-89-0

Chemical Structure| 1082549-89-0

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1082549-89-0 ]

CAS No. :1082549-89-0
Formula : C36H31BN2O2
M.W : 534.45
SMILES Code : CC1(C)C(C)(C)OB(C2=CC(N3C4=C(C5=C3C=CC=C5)C=CC=C4)=CC(N6C7=C(C8=C6C=CC=C8)C=CC=C7)=C2)O1
MDL No. :N/A
InChI Key :ADMPYRNBAYKWOL-UHFFFAOYSA-N
Pubchem ID :59372091

Safety of [ 1082549-89-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1082549-89-0 ]

* 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.

  • Downstream synthetic route of [ 1082549-89-0 ]

[ 1082549-89-0 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 1082549-89-0 ]
  • [ 1133023-55-8 ]
  • C213H150N10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.6% With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux; 1.0 g (0.53 mmol) of M-3, 1.03 g (1.92 mmol) of (3-(9H-carbazole- 9-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane-2-yl)phenyl)-9H-carbazole, and 0.05 g of tetrakistriphenylphosphine palladium were dissolved in 30 ml_ of tetrahydrofuran (THF) under an argon atmosphere in a 100ml round flask with a thermometer, a reflux condenser, and an agitator, and 15 ml_ of 20% tetratriethyl ammonium hydroxide was added thereto. The resulting mixture was refluxed at 75 0C for 48 hours.When the reaction was complete, the reactant was cooled to room temperature, and was then extracted several times with methylenechloride and washed with water.Then, anhydrous magnesium sulfate was used to remove moisture <n="88"/>from the washed reactant. The resulting product was filtered to remove the solvent.The reactant with no solvent was purified through a silica gel column using a mixed solvent of methylenechloride/hexane in a ratio of 1 :1 and recrystallized in acetone, preparing 0.8 g (52.6%) of white CISH-3.
  • 2
  • [ 1082549-89-0 ]
  • [ 1133023-50-3 ]
  • C165H105N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux; 1.0 g (0.83 mmol) of M-1 , 2.22 g (4.15 mmol) of (3-(9H-carbazole- 9-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane-2-yl)phenyl)-9H-carbazole, and 0.05 g of tetrakistriphenylphosphine palladium were dissolved in 40 ml_ of tetrahydrofuran (THF) under an argon atmosphere in a 100ml round flask with a thermometer, a reflux condenser, and an agitator. 20 mL of 20% tetratriethyl ammonium hydroxide was added thereto. The mixture was refluxed for reaction at 75 0C for 48 hours.When the reaction was complete, the reactant was cooled to room temperature and then extracted with methylenechloride and washed several times.Then, anhydrous magnesium sulfate was used to remove moisture from the reactant. The resulting product was filtered to remove a solvent. After removing the solvent, the reactant was purified with a silica gel column using a mixed solvent of methylenechloride/hexane in a ratio of <n="86"/>1 :1 and recrystallized in a mixed solvent of acetone/hexane, obtaining 1.54 g (85%) of CISH-1.
  • 3
  • [ 1082549-89-0 ]
  • [ 1133023-52-5 ]
  • C165H105N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.8% With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux; 0.8 g (0.66 mmol) of M-2, 1.42 g (2.66 mmol) of (3-(9H-carbazole- 9-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane-2-yl)phenyl)-9H-carbazole, and 0.06 g of tetrakistriphenylphosphinepalladium were dissolved in 30 mL of tetrahydrofuran (THF) under an argon atmosphere in a 100 ml round flask with a thermometer, a reflux condenser, and an agitater. Then, 15 ml_ of 20% tetratriethyl ammonium hydroxide was added thereto and refluxed for reaction at 75 0C for 48 hours.When the reaction was complete, the reactant was cooled to room temperature, and was then extracted several times with methylenechloride and washed.Then, anhydrous magnesium sulfate was used to remove moisture from the reactant, which was then filtered to remove a solvent.The reactant with no solvent was purified through a silica gel <n="87"/>column using a mixed solvent of methylenechloride/hexane in a ratio of 1 :1 , preparing 1.1 g (75.8%) of white CISH-2.
  • 4
  • [ 1082549-89-0 ]
  • [ 1132642-08-0 ]
  • [ 1132642-17-1 ]
YieldReaction ConditionsOperation in experiment
68% With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux; 1.2 g (1.11 mmol) of M-3, 1 ,78 g (3.34 mmol) of a material G (3- (9H-carbazol-9-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole, and 0.06 g (0.05 mmol) of tetraistriphenylphosphinepalladium were dissolved in 30 ml_ of THF (tetrahydrofuran) in a 250ml round flask with a thermometer, a reflux condenser, and an agitator under an argon atmosphere, and 15ml_ of 20% tetratriethylammonium hydroxide was added thereto. The resulting mixture was refluxed for reaction at 75 0C for48 hours.When the reaction was complete, the reactant was cooled to room temperature. The reactant was extracted several times with methylenechloride, and was also washed several times with water. Then, the reactant was treated with anhydrous magnesium sulfate to remove moisture. After it was filtered, the solvent was removed therefrom.The reactant with no solvent was purified through a silica gel column using a solvent of methylenechloride/hexane mixed in a ratio of 1 :2 and recrystallized a mixed solvent of acetone/hexane, obtaining 1.3 g <n="67"/>(68%) of white CISH-4. This material had a maximum light emitting wavelength of 388 nm in a chloroform solution.
  • 5
  • [ 1082549-89-0 ]
  • [ 1132642-09-1 ]
  • C130H86N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux; 1.2 g (1.11 mmol) of M-4, 1 ,78 g (3.34 mmol) of a material G (3-(9H-carbazol-9-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl )-9H-carbazole, and 0.06 g (0.05 mmol) of tetrakistriphenylphosphinepalladium were dissolved in 30 mL of THF (tetrahydrofuran) in a 250ml round flask with a thermometer, a reflux condenser, and an agitator under an argon atmosphere, and 15ml_ of 20% tetratriethylammonium hydroxide was added thereto. The resulting mixture was refluxed for reaction at 75 0C for 48 hours.When the reaction was complete, the reactant was cooled to room temperature and then extracted several times with methylenechloride, and was also washed several times with water.Then, the reactant was treated with anhydrous magnesium sulfate to remove moisture. After it was filtered, the solvent was removed therefrom. The reactant with no solvent was purified through a silica gel <n="68"/>column using a solvent of methylenechloride/hexane mixed in a ratio of 1 :2 and recrystallized in a mixed solvent of acetone/hexane, obtaining 1.35 g (70%) of white CISH-5. This material had a maximum light emitting wavelength of 386 nm in a chloroform solution.
  • 6
  • [ 1082549-89-0 ]
  • [ 1132917-78-2 ]
  • C174H130N8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux; 1.2 g (0.71 mmol) of M-5, 0.95 g (1.78 mmol) of a material G (3- (9H-carbazol-9-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-9 H-carbazole, and 0.05 g (0.043 mmol) of tetrakistriphenylphosphinepalladium were dissolved in 30 ml_ of THF (tetrahydrofuran) in a 250ml round flask with a thermometer, a reflux condenser, and an agitator, and 15mL of 20% tetratriethylammonium hydroxide was added thereto. The resulting mixture was refluxed for reaction at 75 0C for 48 hours. When the reaction was complete, the reactant was cooled to room temperature and then extracted several times with methylenechloride, and was also washed several times with water.Then, the reactant was treated with anhydrous magnesium sulfate to remove moisture. After it was filtered, the solvent was removed therefrom. <n="71"/>The reactant with no solvent was purified through a silica gel column using a solvent of methylenechloride/hexane mixed in a ratio of 2:3 and recrystallized with a mixed solvent of acetone/hexane, obtaining 0.9 g(54%) of white CISH-8. This material had a maximum light emitting wavelength of 386 nm in a chloroform solution.
  • 7
  • [ 1082549-89-0 ]
  • [ 1132642-06-8 ]
  • [ 1132642-13-7 ]
YieldReaction ConditionsOperation in experiment
73.3% With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux; 1 2 g (1 27 mmol) of M-1 , 1 ,71 g (3.19 mmol) of a material G (3- (9H-carbazol-9-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole), and 0 06 g (0.05 mmol) of tetrakistriphenylphosphine palladium were dissolved in 30 mL of THF (tetrahydrofuran) in a 250ml round flask with a thermometer, a reflux condenser, and an agitator, and15ml_ of 20% tetratriethylammonium hydroxide was added thereto The resulting mixture was refluxed for reaction at 75 0C for 48 hours.When the reaction was complete, the reactant was cooled to room temperature and then extracted several times with methylenechloride and washed several times with water.Then, the reactant was treated with anhydrous magnesium sulfate to remove moisture. After the resulting product was filtered, the solvent was removed.The reactant without the solvent was purified through a silica gel column using a solvent of methylenechloride/hexane mixed in a ratio of 2:3 and recrystallized in a mixed solvent of methylenechloride/hexane, obtaining 1.49 g (73.3%) of white CISH-1. This material had a maximum light emitting wavelength of 365 nm in a chloroform solution.
  • 8
  • [ 1082549-89-0 ]
  • [ 1132642-07-9 ]
  • [ 1132642-14-8 ]
YieldReaction ConditionsOperation in experiment
78.8% With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 75℃; for 48h;Heating / reflux; 1.2 g (1.27 mmol) of M-2, 1 ,71 g (3.19 mmol) of a material G (3-(9H-carbazol-9-yl)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole, and 0.06 g (0.05 mmol) of tetrakistriphenylphosphinepalladium were dissolved in 30 ml_ of THF(tetrahydrofuran) in a 250 ml round flask with a thermometer, a reflux condenser, and an agitator under an argon atmosphere, and 15ml_ of 20% tetratriethylammonium hydroxide was added thereto. The resulting mixture was refluxed for reaction at 75 0C for 48 hours.When the reaction was complete, the reactant was cooled to room temperature and extracted several times with methylenechloride, and was also washed several times with water. Then, the washed reactant was treated with anhydrous magnesium sulfate to remove moisture. After the resulting product was filtered, the solvent was removed therefrom.The reactant with no solvent was purified through a silica gel column using a solvent of methylenechloride/hexane mixed in a ratio of 2:3 and recrystallized in a mixed solvent of methylenechloride/hexane, obtaining 1.6 g (78.8%) of white CISH-2. This material had a maximum <n="65"/>light emitting wavelength of 363 nm in a chloroform solution.
  • 9
  • [ 61676-62-8 ]
  • [ 750573-24-1 ]
  • [ 1082549-89-0 ]
YieldReaction ConditionsOperation in experiment
65.4% Step 4: Synthesis of Intermediate (F)35.0 g (72 mmol) of the intermediate (E) was dissolved in 350 ml of tetrahydrofuran and added with 61.5 ml (98 mmol) of an n-butyllithium hexane solution (1.6M) under an argon atmosphere at -70 C. The obtained solution was agitated at -70 C. to 40 C. for 1 hour. The reaction flux was frozen to -70 C. and slowly added with 29.3 ml (144 mmol) of isopropyl tetramethyl dioxaborolane in a dropwise fashion. The obtained solution was agitated at -70 C. for 1 hour, and heated to room temperature and agitated for 6 hours. The obtained reaction solution was added with 200 ml of water and agitated for 20 minutes.After the reaction solution was separated into two liquid layers, an organic layer thereof was dried with anhydrous sodium sulfate. After the organic solvent was removed under a reduced pressure, the obtained residue was purified with silica gel column chromatography to provide 25.1 g (yield 65.4%) of the intermediate (F).
  • 10
  • [ 626-39-1 ]
  • [ 1082549-89-0 ]
  • [ 1233491-85-4 ]
YieldReaction ConditionsOperation in experiment
1.3 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; for 24h;Inert atmosphere; Reflux; Intermediate 2 (2 g, 3.7 mmol), 1,3,5-tribromo benzene (5.9 g, 18.7 mmol), tetrakis (triphenylphosphine) palladium (0) (0.1 g, 0.1 mmol) in the THF It was dissolved in a nitrogen stream. Put potassium carbonate (1 M, 30 ml) was stirred and refluxed for 24 hours up to temperature. After the distilled water and extracted with MC, by the MC / Hexane solvent mixture as a developing solvent to conduct column chromatography to give the intermediate 3 in 1.3 g.
  • 13
  • [ 625-92-3 ]
  • [ 1082549-89-0 ]
  • [ 1082549-91-4 ]
YieldReaction ConditionsOperation in experiment
64.4% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; toluene; for 9h;Reflux; Step 5: Synthesis of Intermediate (G)45.1 g (84 mmol) of the intermediate (F), 20.0 g (84 mmol) of 3,5-dibromopyridine, and 2.44 g (2.1 mmol) of tetrakis-(triphenyl phosphine) palladium were suspended in 600 ml of tetrahydrofuran and 400 ml of toluene, and then the suspension was added with a solution in which 23.3 g (169 mmol) of potassium carbonate was dissolved in 400 ml of water. The obtained mixture was heated and refluxed for 9 hours. The reaction fluid was separated into two layers, and an organic layer thereof was cleaned with a sodium chloride saturated aqueous solution and dried with anhydrous sodium sulfate.The organic solvent was removed by distillation under a reduced pressure, and the residue was recrystallized by toluene. The precipitated crystals were separated by filtration and cleansed with toluene to provide 30.7 g (64.4%) of the intermediate (G).
  • 14
  • [ 1082549-89-0 ]
  • C51H33N3 [ No CAS ]
  • 15
  • [ 1082549-89-0 ]
  • [ 1082549-52-7 ]
  • 16
  • [ 1082549-89-0 ]
  • [ 106-37-6 ]
  • [ 61676-62-8 ]
  • [ 1082549-97-0 ]
YieldReaction ConditionsOperation in experiment
Step 2: Synthesis of Intermediate (K)10.3 g of the intermediate (F) synthesized in Example 2, 3.0 g of 1,4-dibromobenzene, 17.58 g of potassium carbonate, and 0.73 g of tetrakis-(triphenylphosphine) palladium were suspended in 200 ml of tetrahydrofuran, 200 ml of toluene, and 50 ml of purified water, and heated and refluxed under a nitrogen atmosphere for 24 hours.15 ml of an n-butyl lithium hexane solution (1.6M) was added and then the obtained solution was agitated at -70 C. for 30 minutes, and the reaction fluid was slowly added with 47.9 ml (235 mmol) of isopropyl tetramethyl dioxaborolane in a dropwise fashion. After the obtained solution was agitated at -70 C. for 1 hour, it was heated to room temperature and agitated for 6 hours. To the obtained reaction solution, 200 ml of water was added and agitated for 20 minutes. After the reaction solution was separated into two liquid layers, an organic solvent thereof was removed under a reduced pressure. The obtained residue was purified with silica gel column chromatography to provide 6 g of the intermediate (K).
  • 17
  • [ 750573-24-1 ]
  • [ 73183-34-3 ]
  • [ 1082549-89-0 ]
YieldReaction ConditionsOperation in experiment
91% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 3h;Inert atmosphere; Reflux; A three-necked flask of 2000ml, equipped with mechanical stirring, Ar gas protection.Was added 3,5-bis (carbazol-9-yl) bromobenzene 9.72 g (molecular weight 486,0.02mol), with boronic acid pinacol ester 5.6 g (molecular weight 254.2, 0.022mol) frequency, Pd (dppf) Cl23.2g (0.0044mol), potassium acetate 36g (molecular weight 138,0.26mol), 1,4-dioxane 500ml.Mechanical agitation, ventilation kept under reduced pressure Ar atmosphere for three times, the reaction was monitored by TLC (thin layer chromatography), to the starting material completely disappeared after 3 hours reflux the reaction was complete.Allowed to cool, the reaction system was divided into two layers, the organic layer was separated, evaporated to dryness, to give the product 9.72g, 91.0% yield.
72% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In 1,4-dioxane; at 80℃; for 12h;Inert atmosphere; The purified compound (1) (1.7 g, 3.5 mmol), bis(pinacolato)diboron (0.93 g, 3.6 mmol),potassium acetate (0.68 g, 6.9 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.2 g,0.2mmol) were dissolved in 1,4-dioxane (50mL) and a nitrogen atmosphere. After themixedsolution was stirred for 12 h at 80C, the reaction mixture was cooled to room temperature.The mixture extracted with dichloromethane (50 mL × 3 times) and dried over anhydrousMgSO4. The crude product was subjected to flash column chromatography (ethyl acetate:n-hexane = 1: 10) to give compound (2) (1.3 g, 72%). 1H NMR (CDCl3, 300 MHz); δ = 7.68(d, -CH-), 7.5 (d, -CH-), 7.45 (d, -CH-), 7.35 (m-CH-), 7.29(t, -CH3), 7.18(m, -CH-), 1.5(-CH3).
71% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; at 100℃; for 24h; 13.68 g (28.07 mmol) of Intermediate (G), 10.69 g (42.10 mmol) of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane), 1.23 g (1.68 mmol) of PdCl2(dppf).CH2Cl2, and 8.26 g (84.20 mmol) of potassium acetate were mixed with 140 mL of dimethyl formamide, followed by stirring at a temperature of 100 C. for 24 hours. Once the reaction was complete, the resulting mixture was cooled to room temperature and filtered through silica gel under reduced pressure. The obtained filtrate was concentrated under reduced pressure, and the resulting product was separated and purified by silica gel column chromatography and recrystallized using dichloromethane/n-hexane to obtain a desired compound, 10.62 g of Intermediate (H) (at a yield of 71%). LC-Mass (calculated value: 534.25 g/mol, measured value: M+1=535 g/mol)
70% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In 1,4-dioxane; for 12h;Inert atmosphere; Reflux; 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole) (6 g, 12.3 mmol), Bis(pinacolato)diboron(4.7 g, 18.4 mmol), potassium acetate (3.6 g, 37 mmol), and Pd(PPh3)4 (0.4 g, 0.3 mmol) were dissolved in distilled 1,4-dioxane. The reaction mixture was refluxed for 12 hours under nitrogen and then allowed to cool to room temperature. After the mixture washed with ethyl acetate, the solvent was removed under vacuum. The crude material was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3 as eluent) to give the title compound 1 (yield: 70%). 1HNMR(CDCl3): δ (ppm) 8.20 (d, 6H), 7.60-7.40 (m, 9H), 7.35-7. 26 (m, 4H),1.30-1.45 (m, 12H).
70% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In 1,4-dioxane; for 12h;Reflux; Inert atmosphere; 9,9-(5-bromo-1,3-phenylene)bis(9H-carbazole) (6 g,12.3 mmol), Bis(pinacolato)diboron (4.7 g, 18.4 mmol),potassium acetate (3.6 g, 37 mmol), and Pd(PPh34(0.4 g, 0.3 mmol) were dissolved in distilled 1,4-dioxane.The reaction mixture was refluxed for 12 hours undernitrogen and then allowed to cool to room temperature.After the mixture washed with ethyl acetate, the solventwas removed under vacuum. The crude material waspurified by column chromatograph on silica gel (ethylacetate:hexane = 1:3 as eluent) to give the title compound1 (yield: 70%). 1H NMR (CDCl3: (ppm) 8.20 (d, 6H),7.60-7.40 (m, 9H), 7.35-7.26 (m, 4H), 1.30-1.45 (m, 12H).
65% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 60 - 80℃; for 14h;Inert atmosphere; Intermediate compound (1) (16.4 g, 33.6 mmol),Bis (pinacolato) diboron (17.1g, 67.2mmol)And potassium acetate (32.97 g, 336 mmol) dissolved in 1,4-dioxane (200 ml),It was then stirred at about 60 C for about 15 minutes under a nitrogen atmosphere.Pd(dppf)CH2Cl2 (0.82 g, 1.0 mmol) was added to the reaction mixture and stirred at about 80 C for about 14 hours.The reaction mixture was cooled to room temperature, extracted with toluene, dried over MgSO 4 to remove water, and then separated by column chromatography (hexane: methylene chloride (MC) = 1:3, v/v).The intermediate compound (2) (11.76 g, yield: 65%) was obtained.
53% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 12h;Reflux; Compound 1-2 64 g (131 mmol),50 g (197 mmol) of bis (pinacolato) diboron,Pd(dppf)Cl2 ([1,1'-bis (diphenylphosphine)ferrocene]dichloropalladium (II)), 4.8 g (6.55 mmol),25.7 g (262 mmol) of potassium acetate was suspended in 500 mL of 1,4-dioxane, and then refluxed and stirred for 12 hours.Extraction with dichloromethane and distilled waterThe high organic layer is filtered through silica gel. The organic solution was removed and recrystallized to obtain 37.1 g (yield 53%) of compound 1-3.
3 g With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate; In 1,4-dioxane; for 24h;Inert atmosphere; Reflux; 9H-carbazole (6.0 g, 35.7 mmol), and 1,3,5-tribromobenzene (5.0 g, 15.0 mmol), cooper (I) iodide (CuI, 0.7 g, 3.6 mmol), potassium carbonate (4.9 g, 35.7 mmol), 1,10-phenanthroline (1,10-phenanthroline, 0.6 g, 3.6 mmol) is dissolved in DMF to insert.Looking up the temperature under the flow of nitrogen was stirred under reflux for 12 hours.After extracting the reaction solution was subjected to column chromatography on MC MC / Hexane solvent mixture as a developing solvent to give the intermediate 1 of about 2 g. Intermediate 1 (4 g, 8.2 mmol) and 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2- dioxane)See above) (3.12 g, 12.3 mmol), potassium acetate (2.4 g, 24.0 mmol), 1,1 '- bis (diphenylphosphino) ferrocene (1,1'-bis (diphenylphosphino) ferrocene, 0.2 g, 0.2 mmol) put in 1,4-dioxane (1,4-dioxane) was stirred at reflux for 24 hours under a nitrogen gas stream is dissolved.After having poured to terminate the reaction, distilled water and extracted with MC.MC / Hexane solvent mixture to a column chromatography with a developing solvent to obtain the intermediate 2 LE of 3 g.

  • 18
  • [ 1082549-89-0 ]
  • [ 3842-55-5 ]
  • 9,9′-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9Hcarbazole) [ No CAS ]
  • 19
  • [ 1700-02-3 ]
  • [ 1082549-89-0 ]
  • 9,9′,9″,9′′′-((6-phenyl-1,3,5-triazine-2,4-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole) [ No CAS ]
  • 20
  • [ 1082549-89-0 ]
  • [ 4181-20-8 ]
  • tris[4-(3,5-bis(carbazol-9-yl)phenyl)phenyl]amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; potassium carbonate; In water; toluene; at 100℃; for 2h;Inert atmosphere; General procedure: A mixture of 9-(3-(9H-carbazol-9-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole 1 (3.9 g,7.30 mmol), <strong>[4181-20-8]tris(4-iodophenyl)amine</strong> 3b (1 g, 1.61 mmol),Pd(Ph3P)4 (0.37 g, 0.32mmol), t-Bu3P 50% in toluene(0.3 mL, 0.64mmol), and K2CO3 (4.4 g, 31.8 mmol) in 100 mL of toluene and 50 mL of distilled water was stirred at 100C for 2 days under argon. After completion of the reaction,the mixture was extracted with dichloromethane. The organic layers were then separated, dried over magnesium sulfate, filtered,and concentrated. The residues were purified by column chromatography using silica gel as the stationary phase and an n-hexane: dichloromethanemixture as the eluent to give the requisiteproduct 4b. Yield: 40%;
40% With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; potassium carbonate; In water; toluene; at 100℃; for 48h;Inert atmosphere; To a solution of 9- (3- (9H-carbazol-9-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxa (3.9 g, 7.30 mmol), tris (4-iodophenyl) amine (Formula b) (1 g, 1.61 mmol), Pd Pd3P)4(0.37 g, 0.32 mmol), in toluene t-Bu3P 50% (0.3ml, 0.64 mmol) and K2CO3and the mixture of (4.4 g, 31.8 mmol) under an argon atmosphere for 2 days And stirred at 100 C.After completion of the reaction, the mixture was extracted with dichloromethane.Then, the organic layer was separated, MgSO4was then dried filtered and concentrated.The obtained residue was purified by silica gel column chromatography using n-hexane: dichloromethane as an eluent to obtain a product of formula (2a) as a beige solid (yield: 40%).
  • 21
  • [ 1082549-89-0 ]
  • [ 38257-52-2 ]
  • [4-(3,5-bis(carbazol-9-yl)phenyl)phenyl]diphenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100℃;Inert atmosphere; General procedure: A mixture of <strong>[1082549-89-0]9-(3-(9H-carbazol-9-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole</strong> 1 (2.16g, 4.04 mmol), 4-iodo-N,N-diphenylbenzenamine 3a (1 g,2.69 mmol), Pd(Ph3P)4 (0.31 g, 0.27 mmol), and K2CO3 (1.86 g, 13.47 mmol) in 100 mL of toluene and 50 mL of distilled water was stirred at 100 C overnight under argon. After completion of the reaction, the mixture was extracted with dichloromethane. The organic layers were then separated, dried over magnesium sulfate, filtered, and concentrated. The residues were purified by column chromatography using silica gel as the stationary phase and an n-hexane: dichloromethane mixture as the eluent to give the requisite product 4a. Yield: 61%
61% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; at 100℃;Inert atmosphere; To a solution of 9- (3- (9H-carbazol-9-yl) -5- (4,4,5,5-tetramethyl-1,3,2-dioxa (2.1 g, 4.04 mmol) and 4-iodo-N, N-diphenylbenzenamine (a) (1 g, 2.69 mmol) ), Pd (Pd3P)4(0.31 g, 0.27 mmol) and K2CO3(1.86 g, 13.47 mmol) was stirred overnight at 100 C. under an argon atmosphere.After completion of the reaction, the mixture was extracted with dichloromethane.Then, the organic layer was separated, MgSO4was then dried filtered and concentrated.The obtained residue was purified by silica gel column chromatography using n-hexane: dichloromethane as an eluent to obtain a white solid (yield: 61%).
  • 22
  • [ 1082549-89-0 ]
  • [ 108-36-1 ]
  • 10-(3',5'-di(9H-carbazol-9-yl)-[1,1'-biphenyl]-3-yl)-10H-phenothiazine 5,5-dioxide [ No CAS ]
  • 23
  • [ 1082549-89-0 ]
  • [ 108-36-1 ]
  • 9,9'-(3'-bromo-[1,1'-biphenyl]-3,5-diyl)bis(9H-carbazole) [ No CAS ]
  • 24
  • [ 1082549-89-0 ]
  • [ 106-37-6 ]
  • 9,9'-(4'-bromo-[1,10-biphenyl]-3,5-diyl)bis(9H-carbazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 95℃; for 24h; General procedure: N- (biphenyl-4-yl) -N- (4-bromophenyl)-9,9-dimethyl-9H-fluoren-2-amine (5.2 g, 0.010 mol) inbis (pinacolato) dibron (2.5 g, 0.012 mol),PdCl2 (dppf) (0.4 g, 0.0005 mol), potassium-acetate (2.7 g,0.020 mol) 1,4-dioxane , add 100 mL wasreacted by stirring for 24 hours at 95 . After the reaction cooled to H20:After layer separation the MC columnpurification ( n - Hexane : MC ) to the intermediate 1-1 to obtain 4.0 g (yield 71%)
72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 95℃; for 24h; General procedure: Intermediate 1-1 (5.2 g, 0.010 mol), bis(pinacolato)dibron (2.5 g, 0.012 mol) PdCl2(dppf) (0.4 g, 0.0005 mol), potassium-acetate (2.7 g, 0.020 mol), 100 mL 4-dioxane was reacted with stirring for 24 hours at 95 C the end of the reaction after cooling by H2O:. after layer separation the MC column purification (n-Hexane: MC) to the intermediate 1-2, 4.0 g (yield: 71%) was obtained. (M / z = 563).
General procedure: (2) According to the reaction formula, compound M6 is prepared as follows: a mixture of compound M5 (25.40 g, 56.95 mmol), pinacol biborate (15.85 g, 62.64 mmol) and potassium acetate (16.74 g, 170.90 mmol) are dissolved In anhydrous 1,4-dioxane (200.0 mL). The resulting mixture was degassed with nitrogen for 15 min, and then tris(dibenzylideneacetone) dipalladium (CAS number: 51364-51-30, 52 g, 0.57 mmol) and2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl(0.54 g, 1.14 mmol). After refluxing at 110C for 12 hours under nitrogen, the mixture was filtered immediately. The filtrate was cooled to 0C in the refrigerator, the product was precipitated, and filtered again to obtain compound M6 as a white powder, yield: 65%.
  • 26
  • [ 1082549-89-0 ]
  • C31H19BrN2 [ No CAS ]
  • C61H38N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 120℃; for 2h; A-5 8.0g (16.02mmol), 9,9 '- (5- (4,4,5,5- tetramethyl-dioxa -1,3,2- borane-2-yl) phenyl-1,3- Rennes) bis (9H- cover)(<strong>[1082549-89-0]9,9'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole)</strong>)10.3g(19.22mmol), Tetrakis (triphenylphosphine) palladium (0) 0.93g (0.8mmol), K3PO4 to 10.2g (48.06mmol), 1,4- dioxane (1,4-dioxane), 160mL, 2 hours at 120 C under 32mL H2O It was stirred while refluxing. After the reaction is a rear solid cooling to room temperature produced after the completion of the filter was washed with dichloromethane (dicholoromethane), ethyl acetate (EA), methanol (MeOH). After the solid in dichloromethane (dichloromethane) to all dissolved after silica gel with excess filter to give 10.3g of the desired compound 1-12 (78%).
  • 27
  • [ 1082549-89-0 ]
  • C25H14BrNS [ No CAS ]
  • C55H33N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 120℃; for 7h; E-4 8.0g (18.17mmol), 9,9 '- (5- (4,4,5,5- tetramethyl-dioxa -1,3,2- borane-2-yl) -1 , 3- phenylene)bis (9H-)(<strong>[1082549-89-0]9,9'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole)</strong>)11.85g(21.8mmol), Tetrakis (triphenylphosphine) palladium (0) 1.05g (0.91mmol), K3PO4 11.57g (54.51mmol) 1,4-dioxane (1,4-dioxane), 160mL, 32mL H2O under 7 hours at 120C It was stirred while refluxing. After the reaction was extracted with distilled water and dichloromethane (dichloromethane). Purified to remove the solvent by rotary evaporation The organic layer was dried over anhydrous MgSO4 dichloromethane and hexane by column chromatography as a developing solvent to obtain 9.5g of the desired compound 1-157 (68%).
  • 28
  • [ 1082549-89-0 ]
  • C21H12BrNS [ No CAS ]
  • C51H31N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 6h; Compound 6-3 5g (12.81mmol ) and ((3,5-di(9H-carbazol-9-yl)phenyl)boronicacid) 6.37g (14.09mmol),Pd(PPh3)4 0.74g (0.64mmol), K2CO3 3.5g (25.62mmol) toluene 50ml,ethanol (EtOH) 5ml and 5ml H2O was refluxed at 120C for 6 hour.After cooling to room temperature after completion of the reaction and extracted with distilled water and EA (ethyl acetate). The organic layer was dried over anhydrous MgSO4 then the solvent removed by rotary evaporator and EA (ethyl acetate) and hexane (Hexane) gave after washing to give 6.4g the title compound 85 (69%).
  • 29
  • [ 1082549-89-0 ]
  • C21H12BrNS [ No CAS ]
  • C51H31N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 120℃; for 6h; Compound 8-5 5g (12.81mmol ) and (3,5-di(9H-carbazol-9-yl)phenyl)boronicacid) 6.37g(14.09mmol),Pd(PPh3)4 0.74g (0.64mmol), K2CO3 3.5g (25.62mmol) toluene 50ml,ethanol (EtOH) 5ml and 5ml H2O was refluxed at 120C for 6 hour.After cooling to room temperature after completion of the reaction and extracted with distilled water and EA (ethyl acetate). The organic layer was dried over anhydrous MgSO4 then the solvent removed by rotary evaporator and EA (ethyl acetate) and hexane (Hexane) gave after washing to give 7.1g the title compound 110 (77%).
  • 30
  • [ 1082549-89-0 ]
  • 10-(4-bromophenyl)-10-phenyl-10H-benzo[b]indeno[2,1-d]thiophene [ No CAS ]
  • C57H36N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate; In ethanol; toluene; for 12h;Reflux; Compound1-1-1 4g (8.82 mmol), 9,9'- (5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene) bis (9H-carbazole), 3.45g (8.02 mmol), (tetrakis(triphenylphosphine) palladium), 0.92g (0.80 mmol), potassium carbonate, 3.33g(24.06 mmol ), toluene, H2O, ethanol mixed solutionwas refluxed for 12 hours. When the reaction is complete the resulting solid isdried and then filtered (filter) to give the title compound 24; 2.4g (38%).
  • 31
  • [ 1082549-89-0 ]
  • C26H18ClN [ No CAS ]
  • C56H37N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56.8% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; for 24h;Reflux; Inert atmosphere; Synthesis procedure is the same method as compound A1, the yield of the final product was 56.8%. A mixture of intermediate Ib (10mmol), dibenzo[b,d]furan-4-ylboronic acid (10mmol), Pd(PPh3)4 (0.25g, 0.21 mmol), Na2CO3 solution (2M, 12ml, 24mmol), ethanol (15ml) and toluene (50ml) was loaded into a 250ml three-necked flask. The mixture was degassed and refluxed under nitrogen atmosphere for 24 hours. After cooling, water (50ml) was added to the mixture. The crude product was collected by filtration and the solid powder was washed several times with methanol to remove impurities.
  • 32
  • [ 1205555-26-5 ]
  • [ 73183-34-3 ]
  • [ 1082549-89-0 ]
YieldReaction ConditionsOperation in experiment
32% With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine; In 1,4-dioxane; at 80℃; for 16h;Inert atmosphere; In a four-necked flask, 3,5-bis(carbazol-9-yl)chlorobenzene (4g, 9mmol), bis(pinacolato)diboron (2.4g, 9.4mmol), KOAc (2.5g , 25.8mmol), Pd2(dba)3 (258mg, 0.284mmol), tricyclohexylphosphine (385mg, 1.4mmol) and anhydrous 1,4-dioxane (120ml). The mixture in a nitrogen atmosphere, reacted at 80 deg. C overnight for 16 hours. The reaction solution was poured into water, extracted with ethyl acetate and washed with saturated NaCl (aq). Subsequently, dried over anhydrous magnesium sulfate and the solvent was removed with an evaporator. The residue was purified by column chromatography and obtained 1.5g of product.Yield 32%.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane;Inert atmosphere; Under a protective atmosphere, put the first intermediate, bipinacol borate, 1,1'-bis(diphenylphosphopalladium)ferrocene dichloride in 1,4-bis In the oxane, the reaction produces intermediate 2 (intermediate 2);
  • 33
  • [ 1082549-89-0 ]
  • C25H17ClN2 [ No CAS ]
  • C55H36N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; for 24h;Reflux; Inert atmosphere; Synthesis procedure is the same manner as in compound A1, the final yield of product was 36%. A mixture of intermediate Ib (10mmol), dibenzo[b,d]furan-4-ylboronic acid (10mmol), Pd(PPh3)4 (0.25g, 0.21 mmol), Na2CO3 solution (2M, 12ml, 24mmol), ethanol (15ml) and toluene (50ml) was loaded into a 250ml three-necked flask. The mixture was degassed and refluxed under nitrogen atmosphere for 24 hours. After cooling, water (50ml) was added to the mixture. The crude product was collected by filtration and the solid powder was washed several times with methanol to remove impurities.
  • 34
  • [ 1082549-89-0 ]
  • [ 18419-48-2 ]
  • dimethyldi(4-(3,5-bis-carbazol-9-yl-phenyl)phenyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 100℃;Inert atmosphere; General procedure: A mixture of dibromosilane derivatives A (0.5 g, 1 equiv.),4,4,5,5-tetramethyl-1,3,2-dioxaborolane derivatives B (3 quiv.),Pd(Pd3P)4 (0.2 equiv.) in toluene (30 mL) was added dropwiseK2CO3 (2 M aq. 15 mL) and stirred overnight at 100 C under argon.After the completion of the reaction, the mixture was extractedwith dichloromethane. The organic layers were separated, driedover magnesium sulfate, filtered, and concentrated. The residueswere purified by silica gel column chromatography and thenrecrystallized in acetone or ethanol to give the requisite productsDM4CzDBPSi, DM2CzDBPSi, DP4CzDBPSi. 2.2.2. Dimethyldi(4-(3,5-bis-carbazol-9-yl-phenyl)phenyl)silane(DM4CzDBPSi)Yield: 42%; white solid; m.p.: 349 C; FT-IR (KBr pellet): max3433, 3055, 2953, 1592, 1480, 1454, 1333, 1312, 1229, 1155, 1113,820, 747, 723 cm1; 1H NMR (500 MHz, CDCl3) d 8.19 (d, 8H,J 7 Hz), 7.96 (d, 4H, J 2 Hz), 7.83 (t, 2H, J 2 Hz), 7.69e7.74 (q,8H, J 8.5 Hz), 7.62 (d, 8H, J 8.0 Hz), 7.44e7.48 (m, 8H), 7.32e7.35(m, 8H), 0.62 (s, 6H); 13C NMR (125 MHz, CDCl3) d 144.6, 140.6,140.1, 139.9, 138.4, 135.1, 126.7, 126.3, 124.3, 123.9, 123.7, 120.6,120.5, 109.8, 31.0; GC-MS: 1025.24 for C74H53N4Si [MH]; HRMS(m/z, FAB) Calcd for C74H53N4Si [MH] 1025.4040, found1025.4038.
  • 35
  • [ 1082549-89-0 ]
  • [ 18733-91-0 ]
  • diphenyldi(4-(3,5-bis-carbazol-9-yl-phenyl)phenyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 100℃;Inert atmosphere; General procedure: A mixture of dibromosilane derivatives A (0.5 g, 1 equiv.),4,4,5,5-tetramethyl-1,3,2-dioxaborolane derivatives B (3 quiv.),Pd(Pd3P)4 (0.2 equiv.) in toluene (30 mL) was added dropwiseK2CO3 (2 M aq. 15 mL) and stirred overnight at 100 C under argon.After the completion of the reaction, the mixture was extractedwith dichloromethane. The organic layers were separated, driedover magnesium sulfate, filtered, and concentrated. The residueswere purified by silica gel column chromatography and thenrecrystallized in acetone or ethanol to give the requisite productsDM4CzDBPSi, DM2CzDBPSi, DP4CzDBPSi.
  • 36
  • [ 1082549-89-0 ]
  • 9'H-9,1':3',9''-tercarbazole [ No CAS ]
  • 37
  • [ 1082549-89-0 ]
  • 9'-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'H-9,1':3',9''-tercarbazole [ No CAS ]
  • 38
  • [ 1082549-89-0 ]
  • [ 577-19-5 ]
  • 9,9'-(2'-nitro-[1,1'-biphenyl]-3,5-diyl)bis(9H-carbazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; toluene; at 80℃; for 12h;Inert atmosphere; Intermediate compound (2) (11.76 g, 22 mmol)And 1-bromo-2-nitrobenzene (3.68 g, 18.2 mmol) in dioxane / toluene (30 ml / 30 ml),K2CO3 (7.6 g, 55 mmol) and distilled water (10 ml) were added to the reaction mixture.It was then stirred under a nitrogen atmosphere for about 20 minutes.Then, Pd(PPh3)4 (0.8 g, 0.69 mmol) was added thereto, and the reaction mixture was stirred at about 80 C for about 12 hours.After completion of the reaction, the reaction temperature was lowered to room temperature, and the reaction product was extracted with ethyl acetate (EA) (100 ml), and dried with MgSO 4 to remove water.And separated by column chromatography (n-hexane: EA = 10:1, v/v),Intermediate compound (3) (8.02 g, yield 69%) was obtained.
  • 39
  • [ 1082549-89-0 ]
  • [ 81725-16-8 ]
  • C38H22N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; for 24h;Inert atmosphere; Reflux; General procedure: Intermediate 2 (2 g, 3.7 mmol), 1,3,5-tribromo benzene (5.9 g, 18.7 mmol), tetrakis(triphenylphosphine)palladium (0) (0.1 g, 0.1 mmol) in the THF It was dissolved in a nitrogen stream. Put potassium carbonate (1 M, 30 ml) was stirred and refluxed for 24 hours up to temperature. After the distilled water and extracted with MC, by the MC / Hexane solvent mixture as a developing solvent to conduct column chromatography to give the intermediate 3 in 1.3 g. In place of 1,3,5-tribromo-2-iodo-benzene-1,3-dicyano benzene (2-iodo-1,3-dicyanobenzene), and the formula used to manufacture similar to the method of Intermediate 3 Compound 7 to give a compound yield of 60%.
  • 40
  • 2,4-bis(4-(tert-butyl)phenyl)-6-chloro-1,3,5-triazine [ No CAS ]
  • [ 1082549-89-0 ]
  • 9,9'-(5-(4,6-bis(4-(tert-butyl)phenyl)-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; 2,4-Bis(4-(tert-butyl)phenyl)-6-chloro-1,3,5-triazine (1) (0.8 g,2.1 mmol) and 9,90-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole) (1.3 g, 2.3 mmol) were dissolvedin anhydrous THF (30 ml). After 30 min, tetrakis(-triphenylphosphine)palladium (15.0 mg, 0.1 mmol) and 2 Maqueous potassium carbonate (6.9 g, with distilledwater 15 ml)wasadded in above mixture continuously. The residuewas extracted bymethylene chloride and distilled water. And then solvent wasremoved from the resulting mixture under reduced pressure. Thecrude product was purified by column chromatography on silica gelusing n-hexane/methylene chloride. The product was sublimed andobtained as a greenishyellow powder (1.2 g, yield 76%).1HNMR(500MHZ, CDCl3): 9.10 (s, 2H), 8.65e8.63 (d, 4H, J 5.0 Hz), 8.21e8.19 (d,4H, J 3.7 Hz), 8.04e8.03 (t, 1H, J 1.3 Hz), 7.64e7.62 (d, 4H,J 4.0 Hz), 7.55e7.53 (d, 4H, J 4.2 Hz), 7.50e7.46 (t, 4H, J 5.5 Hz),7.36e7.35 (t, 4H, J2.5 Hz),1.36 (s,18H) MS (APCI) miz 752.9 [(M)].Elemental Analysis calculated for C53H45N5: C, 84.65; H, 6.03; N,9.31. Found: C, 84.64; H, 6.24; N, 8.75.
  • 41
  • [ 1082549-89-0 ]
  • 2,4-bis[3,5-bis(1,1-dimethylethyl)phenyl]-6-chloro-1,3,5-triazine [ No CAS ]
  • 9,9'-(5-(4,6-bis(3,5-di-tert-butylphenyl)-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃;Inert atmosphere; General procedure: 2-chloro-4,6-bis(3,5-di-tert-butylphenyl)-1 ,3,5-triazine (1.00 equivalents) R1-fluoro- phenylboronic ester (1.00-1.50 equivalents), Pd(PPh3)4 tetrakis(triphenylphosphine)palladium(O) (CAS:14221-01-3, 0.10 equivalents) and potassium carbonate (3.00 equivalents) are stirred overnight under nitrogen atmosphere in THF/Water (3:1 ) at 70 C. After cooling down to room temperature (RT), the reaction mixture is extracted with ethyl acetate/brine. The organic phases are collected, the organic solvent is removed and the crude product Z0 is purified by flash chromatography or by recrystallization.
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; 2-chloro-4,6-bis(3,5-di-tert-butylphenyl)-1,3,5-triazine (2)(1.0 g, 2.0 mmol) and 9,90-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole) (1.2 g,2.2 mmol) were dissolved in anhydrous THF (30 ml). After 30 min,tetrakis(triphenylphosphine)palladium (15.0 mg, 0.1 mmol) and2Maqueous potassium carbonate (6.9 g, with distilledwater 15 ml)was added in above mixture continuously. Work-up procedure ofDtDCzTrz was the same as that of tDCzTrz and the product wasobtained as a yellowish green powder after sublimation (1.1 g, yield63%). 1H NMR (500 MHZ, CDCl3): 9.0 (s, 2H), 8.65e8.65 (d, 4H,J 0.7 Hz), 8.20e8.18 (d, 4H, J 4.0 Hz), 8.12e8.11 (t, 1H, J 1.3 Hz),7.76e7.75 (d, 4H, J 4.0 Hz), 7.70e7.69 (t, 2H, J 1.1 Hz), 7.50e7.46(t, 4H, J 5.5 Hz), 7.36e7.33 (t, 4H, J 5.1 Hz), 1.41 (s, 36H) MS(APCI) miz 865.1 [(M)]. Elemental Analysis calculated forC61H61N5: C, 84.78; H, 7.11; N, 8.10. Found: C, 84.75; H, 6.98; N, 7.87.
  • 42
  • [ 790674-48-5 ]
  • [ 1082549-89-0 ]
  • 2,2'-bis(3,5-di(9H-carbazol-9-yl)phenyl)-9,9'-spirobi[fluorene] [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Reflux; Inert atmosphere; Reactant 1 (0.5 g, 0.935 mmol), 2,2'-diiodo-9,9'-spirobi[fluorene] (0.125 g, 0.425 mmol), and Pd(PPh3)4 (0.024 g, 0.02 mmol) were dissolved in THF (5 mL). An aliquot of 2 N aqueous potassium carbonate (5 mL) was added to the mixture and refluxed for 12 hours under nitrogen. The reaction mixture allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The crude material was purified by column chromatography on silica gel (hexane: ethyl acetate=1:3) to give the spiro-mCP (yield: 60%). 1HNMR (400MHz,CDCl3): δ (ppm) 8.25 (d, 4H), 7.94 (d, 8H), 7.87 (d, 6H), 7.75 (m, 6H), 7.63 (m, 6H), 7.50 (m,6H), 7.33 (m, 6H), 7.29 (t, 6H), 7.12 (s, 4H).
  • 43
  • [ 1082549-89-0 ]
  • 3-phenyl-6-(4-bromophenyl)imidazo[1,2-a]pyrimidine [ No CAS ]
  • C48H31N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 3.5h;Reflux; In a 1000ml three-necked flask, equipped with mechanical stirrer, Ar protection, was added 3-phenyl-6-p-bromophenyl imidazole Step generated above and [1,2-a] pyrimidine 7.2 g of (molecular weight 349, purity 97 %, 0.02mol), 3,5- bis (carbazol-9-yl) phenylboronic acid 11.8 g of knit the brows matter ester (molecular weight 534,0.022mol), catalyst Pd (PPh3)4The amount of 1.8 g of (molecular weight 1154,0.001556mol), aqueous sodium carbonate solution 120ml (2M), toluene 300ml, ethanol 150ml.Was stirred at reflux, the reaction was monitored by TLC, the reaction was complete co 3.5hs reaction.Cooling, was separated, evaporated to dryness and the product isolated by column chromatography eluted with 1: 1 ethyl acetate: petroleum ether to give a pale yellow solid compound 11.76g, purity 99.0%, yield: 86.0%.
  • 44
  • [ 1082549-89-0 ]
  • 6-bromo-2,4,9-triphenyl-9H-pyrimido[4,5-b]indole [ No CAS ]
  • C58H37N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In monoethylene glycol diethyl ether; water; for 16h;Reflux; General procedure: 74.2 g (156 mmol) of 6-bromo-2,4-diphenyl-9H-pyrimido[4,5-b]indole, 49.3 g (172 mmol) of 3-(9H-carbazol-9-yl-phenyl]-boronic acid and 36 g (340 mmol) of sodium carbonate are suspended in 1000 mL ethylene glycol diethyl ether and 280 mL of water. Afterwards, 1 .8 g (1 .5 mmol) of tetrakis(triphenylphosphine)palladium(0) is added to the reaction mixture, which is heated for 1 6 hours under reflux After cooling, the organic phase is separated off, filtered through silica gel and then evaporated to dryness. The product is purified by column chromatography on silica gel with toluene/heptane (1 :2) and finally sublimed in high vacuum (p = 5 x 10-7 mbar) (purity 99.9%). The yield is 84 g (132 mmol), corresponding to 85% of theory.
  • 45
  • [ 768-90-1 ]
  • [ 1082549-89-0 ]
  • 9,9'-{5-[(3r,5r,7r)-adamantan-1-yl]-1,3-Phenylene} bis(9H-carbazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Reactant 1 (1.5 g, 2.8 mmol), 1-bromoadamantane (1.1 g,4.2 mmol), and palladium (0.16 g, 0.14 mmol) were dissolvedin distilled THF. The reaction mixture was thenstirred for 1 hour at room temperature. Potassium carbonatewas added to the reaction mixture. The reaction mixturewas refluxed for 12 hours under nitrogen and thenallowed to cool to room temperature. After the reactionwas finished, the mixture was washed three times with distilledwater and extracted with ethyl acetate. The organiclayer was separated, dried over anhydrous magnesium sulfate,and the solvent was removed under vacuum. Thecrude material was purified by column chromatography onsilica gel (ethyl acetate:hexane= 1:3 as eluent) to give the ad-mCP as a white power product (yield: 60%). 1H NMR(CDCl3: (ppm) 8.26 (d, 4H), 8.20 (S, 2H), 8.0 (s, 1H),7.71 (d, 4H), 7.60 (t, 4H), 7.40 (t, 4H), 1.30-1.50 (m, 9H),1.0-1.10 (m, 6H).
  • 46
  • [ 2039-82-9 ]
  • [ 1082549-89-0 ]
  • 9,9'-(4'-vinylbiphenyl-3,5-diyl)bis(9H-carbazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 80℃; for 12h; The 9,9-(4-vinylbiphenyl-3,5-diyl)bis(9H-carbazole) was prepared by amodified method ofSuzuki coupling [ref]. The compound (2) (1.2 g, 2.2 mmol), 1-bromo-4-vinylbenzene (0.4 g,2.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.2 g, 0.34 mmol) were stirred intetrahydrofuran (100 mL). Potassiumcarbonate solution (2 N, 100 mL) was added to the mixturewhich was then vigorously stirred for 12 h at 80C. The reaction mixture was cooledto room temperature and extracted with dichloromethane (50 mL × 3 times) and driedover anhydrous MgSO4. The crude product was subjected to flash column chromatography(dichloromethane: n-hexane = 1: 5) to give compound (3) (1 g, 77%). 1H NMR (CDCl3,300MHz); δ = 7.68 (d, -CH-), 7.5 (d, -CH-), 7.45 (d, -CH-), 7.35 (m-CH-), 7.29(t, -CH3),7.18(m, -CH-), 6.52(m, -CH), 5.63 (d, -CH), 5.22 (d, -CH-).
  • 47
  • [ 1082549-89-0 ]
  • 5,8-dibromo-2,3-diphenylpyrido[3,4-b]pyrazine [ No CAS ]
  • 9,9',9'',9'''-(5,5'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 12h;Inert atmosphere; 9,9′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole) instead of 3-(9H-carbazol-9-yl) phenyl-boronic acid, except for using the same method as in synthesis Example 2, the desired compound of 25 9,9′,9″,9′″-(5,5′-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis (benzene-5,3,1-triyl))tetrakis(9H-carbazole) (C17) was obtained. MS (m/z, EI+): 1096.4. A mixture of 5 g (11.3 mmol) of 5,8-dibromo-2,3-diphenylpyrido [3,4-b]pyrazine and 7.16 g (24.9 mmol) of 3-(9H-carbazol-9-yl) phenylboronic acid, 0.13 g (0.11 mmol) of Pd(PPh3)4, 14.1 ml of 2M Na2CO3(aq), 50 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 100 C. for 12 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The 250 mL of methanol was added, then filtered and washed by methanol to get the red solid, yield (5.04 g, 59%). MS (m/z , EI+): 765.5.
  • 48
  • [ 1082549-89-0 ]
  • [ 75344-77-3 ]
  • C39H27N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
597.7 mg With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 85℃;Inert atmosphere; (2) Under a nitrogen atmosphere,Add in a 250 ml three-neck round bottom reaction bottle4-bromo-3,5-dimethylbenzonitrile (2 mmol, 420.14 mg) and9,9'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene) bis ( 9H-carbazole) 1.18g, 2.2mmol),Add 120 mL of toluene and 50 mL of ethanol and stir to dissolve.Further, 40 mL of a saturated potassium carbonate solution (2 mol/L) was added.Quickly join after 15 minutes of ventilationPd(PPh3)4 (173.4 mg, 0.15 mmol) was stirred under nitrogen for 15 min.The reaction system was heated to 85 degrees Celsius overnight.The reaction was stopped, and after the temperature was lowered to room temperature, the solvent of the reaction system was removed by rotary evaporation.Extract with dichloromethane solvent and wash 3 times with deionized water.The product was purified by column chromatography, and the eluent was a mixture solvent of petroleum ether and dichloromethane in a ratio of 3:1.Finally, 597.7 mg of a white solid product was obtained in a yield of 55.3%.The yield of the solid product was finally obtained to be 83%.
  • 49
  • [ 1082549-89-0 ]
  • 2-(5-chloro-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine [ No CAS ]
  • C57H37N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With palladium diacetate; potassium carbonate; XPhos; In ethanol; water; toluene; for 12h;Inert atmosphere; Reflux; In the flask, Intermediate 1-1 (2 g, 4.8 mmol) was added in that order.3,5-di(carbazol-9-yl)-phenylboronic acid pinacol ester (2.6 g, 4.8 mmol),Potassium carbonate (1.3 g, 10 mmol), palladium acetate (0.1 g), X-phos (0.3 g),Toluene (20 mL), ethanol (10 mL) and water (10 mL),reflux under nitrogen for 12 hours, cooled, extracted with dichloromethane,Dry and concentrate, and the crude product is purified by column chromatography to obtain 2 g.The yield was 54%.
  • 51
  • [ 1082549-89-0 ]
  • C54H34N4 [ No CAS ]
  • 52
  • [ 1082549-89-0 ]
  • C53H34N4 [ No CAS ]
  • 53
  • [ 1082549-89-0 ]
  • C72H48N4Si [ No CAS ]
  • 54
  • [ 1082549-89-0 ]
  • 1-bromo-4-(2-H-o-carboran-1-yl)-5-methylbenzene [ No CAS ]
  • C39H36B10N2 [ No CAS ]
 

Historical Records

Technical Information

Categories