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Chemical Structure| 1365692-79-0
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Product Details of [ 1365692-79-0 ]

CAS No. :1365692-79-0 MDL No. :MFCD30187267
Formula : C21H25BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OIPUMEUHUKJHRJ-UHFFFAOYSA-N
M.W : 320.23 Pubchem ID :89679259
Synonyms :

Safety of [ 1365692-79-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P363-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1365692-79-0 ]

* 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 [ 1365692-79-0 ]

[ 1365692-79-0 ] Synthesis Path-Downstream   1~49

  • 1
  • [ 942615-32-9 ]
  • [ 25015-63-8 ]
  • [ 1365692-79-0 ]
YieldReaction ConditionsOperation in experiment
90.3% With triethylamine;1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In toluene; at 80℃; for 8h;Inert atmosphere; In a 300-ml three-neck flask, 7.0 g (26.0 mmol) of the compound b-1, 7.57 ml (52.0 mmol) of the compound b-2, 100 ml of toluene, and 20 ml of triethylamine were charged, and 1.4 g of [1, 1 ' -bis (diphenylphosphino) propane] dichloro nickel was added at room temperature in a nitrogenatmosphere under stirring condition. The temperature was increased to 80C, and stirring was performed for 8 hours. After the reaction, an organic layer was extracted with toluene, was then dried using anhydrous sodium sulfate, and was subsequently refined using a silica gel column (mixture of toluene and heptane: developing solvent), so that 7.45 g of the compound b-3 (white oil) (yield: 90.3%) was obtained.
  • 2
  • [ 31928-44-6 ]
  • [ 1365692-79-0 ]
  • [ 1365692-80-3 ]
YieldReaction ConditionsOperation in experiment
69.7% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 12h;Inert atmosphere; In a 300-ml three-neck flask, 9.69 g (35.9 mmol) of the compound b-3, 17.0 g (53.6 mmol) of the compound b-4, 32.5 g (100 mmol) of cesium carbonate, 100 ml of toluene, 50 ml of ethanol, and 50 ml of water were charged in a nitrogen atmosphere, and 2.07 g oftetrakis (triphenylphosphine ) palladium ( 0 ) was added at room temperature in a nitrogen atmosphere under stirringcondition. The temperature was increased to 80C, and stirring was performed for 12 hours. After the reaction, an organic layer was extracted with toluene, was then dried using anhydrous sodium sulfate, and was subsequently refined using a silica gel column (mixture of toluene and heptane: developing solvent), so that 9.56 g of the compound b-5 (white oil) (yield: 69.7%) was obtained.
  • 3
  • [ 1365692-79-0 ]
  • [ 1365692-81-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 80 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere
  • 4
  • [ 1365692-79-0 ]
  • [ 1365692-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 80 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere 3: potassium phosphate; water / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 5 h / 80 °C / Inert atmosphere
  • 5
  • [ 1365692-79-0 ]
  • [ 1365692-96-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 80 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere 3: potassium phosphate; water / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 5 h / 80 °C / Inert atmosphere
  • 6
  • [ 1365692-79-0 ]
  • [ 1365692-98-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 80 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere 3: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / cyclohexane / 8 h / 100 °C / Inert atmosphere
  • 7
  • [ 1365692-79-0 ]
  • [ 1365692-99-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 80 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere 3: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / cyclohexane / 8 h / 100 °C / Inert atmosphere 4: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 5 h / 80 °C / Inert atmosphere
  • 8
  • [ 1365692-79-0 ]
  • [ 1365693-00-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 80 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere 3: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / cyclohexane / 8 h / 100 °C / Inert atmosphere 4: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 5 h / 80 °C / Inert atmosphere 5: potassium phosphate; water / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene / 5 h / 80 °C / Inert atmosphere
  • 9
  • [ 1365692-79-0 ]
  • [ 615-36-1 ]
  • C21H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 120℃; for 3h; C-2 Synthesis of Compound C-2 C-1 17.3g (54.02mmol), 2- bromoaniline (2-bromoaniline), 18.6g (108.04mmol), tetrakis (triphenylphosphine) palladiumRhodium (0) 3.12g (2.70mmol), K3PO4 34.4g (162.06mmol) 1,4-dioxane (1,4-dioxane) 170mL, and stirred under reflux for 3 hours under 120 °C 30mL H2O. After the reaction was complete, after cooling to room temperature and extracted with distilled water and dichloromethane (dichloromethane). Then filter to remove the solvent by rotary evaporation The organic layer was dried over anhydrous MgSO4 given silica gel and washed with hexane and methanol (MeOH) (small quantity) to give the title compound C-2 13.0g (84%).
  • 10
  • [ 942615-32-9 ]
  • [ 73183-34-3 ]
  • [ 1365692-79-0 ]
YieldReaction ConditionsOperation in experiment
81% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 120℃; for 16h; <strong>[942615-32-9]4-bromo-9,9-dimethyl-fluorene</strong> -9H- (4-Bromo-9,9-dimethyl-9H-fluorene) 20g (73.21mmol), bis (pinacolato) diboron 37.2g (146.43mmol) , potassium acetate (KOAc), 21.5g (219.63mmol), [1,1'- bis (diphenylphosphino) ferrocene] dichloropalladium (II) the dimethyl 2.68g (3.66mmol), dimethylformamide (DMF) under 120C 200mL with stirring for 16 hours. After the reaction was complete, after cooling to room temperature and extracted with distilled water and dichloromethane (dichloromethane). Then filter to remove the solvent by rotary evaporation The organic layer was dried over anhydrous MgSO4 given silica gel washed with hexane to give the title compound C-1 19.0g (81%).
77% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 120℃; After <strong>[942615-32-9]4-bromo-9,9-dimethyl-9H-fluorene</strong> (50.0 g, 183 mmol) was dissolved in DMF (915 mL), bis (pinacolato) diboron (51.1 g, 201 mmol), KOAc (53.9 g, 549 mmol) ), PdCl 2 (dppf) (4.02 g, 5.49 mmol) was added and stirred at 120 C. When the reaction is complete, DMF is removed by distillation and extracted with CH 2 Cl 2 and water. After extraction is completed, the organic layer is dried over MgSO 4 and concentrated. Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 45.1 g (yield: 77%) of the product.
  • 11
  • [ 1365692-79-0 ]
  • C28H22BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 3 h / 120 °C 2: triethylamine / dichloromethane / 1 h / 0 °C
  • 12
  • [ 1365692-79-0 ]
  • C28H20BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 3 h / 120 °C 2: triethylamine / dichloromethane / 1 h / 0 °C 3: trichlorophosphate / nitrobenzene / 2 h / 150 °C
  • 13
  • [ 1365692-79-0 ]
  • C33H20ClN3 [ No CAS ]
  • C48H33N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 18h; Inert atmosphere; 12 Synthesis Example 12: Synthesis of Compound 7 Intermediate 1-2 (10 g, 20.2 mmol) was dissolved in tetrahydroffiran (THF, 0.1 L) under a nitrogen environment, 4-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetram- ethyl-1,3,2-dioxaborolane (7.13 g, 22.3 mmol, purchased from Zhengzhon HQ Material), tetrakis(triphenylphosphine) palladium (0.23 g, 0.20 mmol), and potassium carbonate saturated in water (6.98 g, 50.5 mmol) were added thereto, and the mixture was heated and refluxed at 80° C. for 18 hours. After the reaction was complete, water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM) and treated with anhydrous MgSO4 to remove moisture, and the resultant was filtered and concentrated under a reduced pressure. A residue obtained in this way was separated and purified through flash column chromatography to obtain Compound 7 (7.64 g, 58%).HRMS (70 eV, EI+): mlz calcd for C48H33N3:651.2674, found: 651.Elemental Analysis: C, 88%; H, 5%
  • 14
  • [ 1365692-79-0 ]
  • C45H32BrN3Si [ No CAS ]
  • C60H45N3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 3h; Inert atmosphere; Reflux; 16 Synthesis of intermediate 76-2: General procedure: 43.5 g of intermediate 76-1 was dissolved in 500 ml of 1,4-dioxane solvent.Stir under nitrogen, and add 23.4 g of 4-bromo-3-chlorobenzeneboronic acid, 41.4 g of potassium carbonate, 50 ml of water,1.15g of tetrakis(triphenylphosphine)palladium, the temperature was raised to reflux reaction, and the reaction of the raw materials was completed after 3 hours.After the reaction solution was dried under reduced pressure,36.7 g of Intermediate 76-2 (yield 67%) was obtained by column chromatography.
  • 15
  • [ 1365692-79-0 ]
  • 6-bromo-3-iodothiophene[2,3-b]pyrazine [ No CAS ]
  • C71H49N3SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 12 h / 85 °C / Inert atmosphere 2: palladium diacetate / toluene / 12 h / 120 °C / Inert atmosphere
  • 16
  • [ 1365692-79-0 ]
  • 6-bromo-3-iodothiophene[2,3-b]pyrazine [ No CAS ]
  • 6-bromo-3-(9,9-dimethyl-9H-fluoren-4-yl)thiophene[2,3-b]pyrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 12h; Inert atmosphere; 8.2 2) In a 500ml three-neck bottle,Add 6-bromo-3-iodothiophene [2,3-b]pyrazine (34.10 g, 100 mmol),9,9-dimethyl-9H-indol-4-yl-2-boronic acid ester (32.02 g, 100 mmol),Potassium carbonate (27.64 g, 200 mmol), 150 g of toluene,75 g of ethanol, 75 g of water, and added tetrakis(triphenylphosphine)palladium under the protection of N2.After reacting at 85 ° C for 12 h, the reaction was completed 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, decolorized by adding activated carbon, and filtered.The solvent was distilled off under reduced pressure, and then recrystallized twice with ethyl acetate.Drying under vacuum gave the intermediate 6-bromo-3-(9,9-dimethyl-9H-indol-4-yl)thiophene[2,3-b]pyrazine.
  • 17
  • [ 1365692-79-0 ]
  • C29H21N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 200 °C
  • 18
  • [ 1365692-79-0 ]
  • [ 17024-21-4 ]
  • C29H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; 1.4.9.2 (2) Synthesis of Sub 4-70b After dissolving Sub 4-70a (45.1 g, 141 mmol) obtained in the above synthesis in THF (740 mL), 9-bromo-10-nitrophenanthrene (42.5 g, 141 mmol), K 2 CO 3 (58.4 g, 422 mmol) ), Pd (PPh 3 ) 4 (9.76 g, 8.45 mmol), water (352 mL) was added and stirred at 80 ° C. After the reaction was completed, extracted with CH 2 Cl 2 and water, the organic layer was dried over MgSO 4 and concentrated. Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 36.3 g (yield: 62%) of the product.
  • 19
  • [ 1365692-79-0 ]
  • 1-bromo-N,N-diphenyl-9H-carbazol-3-amine [ No CAS ]
  • C45H34N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 20
  • [ 1365692-79-0 ]
  • 1-bromo-N,N-diphenyl-9H-carbazol-3-amine [ No CAS ]
  • 1-(9,9-dimethyl-9H-fluoren-4-yl)-N,N-diphenyl-9H-carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
32 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 8h; 217 Synthesis of 1-(dibenzo[b,d]furan-4-yl)-9H-carbazole General procedure: 1-bromo-9H-carbazole (50g, 203mmol), 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 65.7g, 223mmol), K2CO3 (56.1g, 406mmol), Pd(PPh3)4 (11.7g, 10.15mmol) and 200ml/200ml/40ml of Toluene/EtOH/H2O were added and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 59.5 g (88%) of the target compound was obtained by column chromatography.
  • 21
  • [ 1365692-79-0 ]
  • N,N-di([1,1'-biphenyl]-4-yl)-1-bromo-9H-carbazol-3-amine [ No CAS ]
  • C63H46N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 22
  • [ 1365692-79-0 ]
  • N,N-di([1,1'-biphenyl]-4-yl)-1-bromo-9H-carbazol-3-amine [ No CAS ]
  • N,N-di([1,1'-biphenyl]-4-yl)-1-(9,9-dimethyl-9H-fluoren-4-yl)-9H-carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
38 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 8h; 218 Synthesis of 1-(dibenzo[b,d]furan-4-yl)-9H-carbazole General procedure: 1-bromo-9H-carbazole (50g, 203mmol), 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 65.7g, 223mmol), K2CO3 (56.1g, 406mmol), Pd(PPh3)4 (11.7g, 10.15mmol) and 200ml/200ml/40ml of Toluene/EtOH/H2O were added and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 59.5 g (88%) of the target compound was obtained by column chromatography.
  • 23
  • [ 1365692-79-0 ]
  • N-([1,1'-biphenyl]-4-yl)-1-bromo-N-(9,9-dimethyl-9H-fluoren-2-yl)-9H-carbazol-3-amine [ No CAS ]
  • C66H50N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 24
  • [ 1365692-79-0 ]
  • N-([1,1'-biphenyl]-4-yl)-1-bromo-N-(9,9-dimethyl-9H-fluoren-2-yl)-9H-carbazol-3-amine [ No CAS ]
  • N-([1,1'-biphenyl]-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-1-(9,9-dimethyl-9H-fluoren-4-yl)-9H-carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
35 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 8h; 219 Synthesis of 1-(dibenzo[b,d]furan-4-yl)-9H-carbazole General procedure: 1-bromo-9H-carbazole (50g, 203mmol), 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 65.7g, 223mmol), K2CO3 (56.1g, 406mmol), Pd(PPh3)4 (11.7g, 10.15mmol) and 200ml/200ml/40ml of Toluene/EtOH/H2O were added and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 59.5 g (88%) of the target compound was obtained by column chromatography.
  • 25
  • [ 1365692-79-0 ]
  • 1-bromo-N,N-di(naphthalen-2-yl)-9H-carbazol-3-amine [ No CAS ]
  • C59H42N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 26
  • [ 1365692-79-0 ]
  • 1-bromo-N,N-di(naphthalen-2-yl)-9H-carbazol-3-amine [ No CAS ]
  • 1-(9,9-dimethyl-9H-fluoren-4-yl)-N,N-di(naphthalen-2-yl)-9H-carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
41 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 8h; 220 Synthesis of 1-(dibenzo[b,d]furan-4-yl)-9H-carbazole General procedure: 1-bromo-9H-carbazole (50g, 203mmol), 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 65.7g, 223mmol), K2CO3 (56.1g, 406mmol), Pd(PPh3)4 (11.7g, 10.15mmol) and 200ml/200ml/40ml of Toluene/EtOH/H2O were added and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 59.5 g (88%) of the target compound was obtained by column chromatography.
  • 27
  • [ 1365692-79-0 ]
  • N-([1,1'-biphenyl]-4-yl)-1-bromo-N-(naphthalen-2-yl)-9H-carbazol-3-amine [ No CAS ]
  • N-([1,1'-biphenyl]-4-yl)-1-(9,9-dimethyl-9H-fluoren-4-yl)-N-(naphthalen-2-yl)-9H-carbazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
45 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 8h; 221 Synthesis of 1-(dibenzo[b,d]furan-4-yl)-9H-carbazole General procedure: 1-bromo-9H-carbazole (50g, 203mmol), 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 65.7g, 223mmol), K2CO3 (56.1g, 406mmol), Pd(PPh3)4 (11.7g, 10.15mmol) and 200ml/200ml/40ml of Toluene/EtOH/H2O were added and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 59.5 g (88%) of the target compound was obtained by column chromatography.
  • 28
  • [ 1365692-79-0 ]
  • C61H44N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 29
  • [ 1365692-79-0 ]
  • C45H34N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 30
  • [ 1365692-79-0 ]
  • C63H44N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 31
  • [ 1365692-79-0 ]
  • C66H48N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 32
  • [ 1365692-79-0 ]
  • C59H40N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 33
  • [ 1365692-79-0 ]
  • C61H42N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 100 °C 2: XPhos; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 120 °C
  • 34
  • [ 16807-11-7 ]
  • [ 1365692-79-0 ]
  • 1-(9,9-dimethyl-9H-fluoren-4-yl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
38 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 8h; 171 Synthesis of 1-(dibenzo[b,d]furan-4-yl)-9H-carbazole General procedure: 1-bromo-9H-carbazole (50g, 203mmol), 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ( 65.7g, 223mmol), K2CO3 (56.1g, 406mmol), Pd(PPh3)4 (11.7g, 10.15mmol) and 200ml/200ml/40ml of Toluene/EtOH/H2O were added and stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 59.5 g (88%) of the target compound was obtained by column chromatography.
  • 35
  • [ 29504-81-2 ]
  • [ 1365692-79-0 ]
  • C19H15BrS [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃;Inert atmosphere; 32g (100mmol, 1.0eq.) 9,9'-dimethylfluorene-4-boronic acid and 31.8g (110mmol, 1.1eq.) 2-bromo-5-iodo-thiophene were added to a 3L three-necked flask, add 1200ml of toluene and 120ml of ethanol to dissolve, add nitrogen for 15 minutes, then add 150ml of 2M aqueous solution containing 41.5g (300mmol, 3.0eq.) K2CO3, and finally add 2.3gPd(PPh3)4 (2mol%). The temperature was raised to 100C, and the reaction ended overnight. Add activated carbon adsorption, suction filtration, the solvent was removed, dried, and recrystallized with toluene and ethanol to obtain 26.6 g of Intermediate-18 with a yield of 75%.
  • 36
  • [ 1365692-79-0 ]
  • C25H27BO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 100 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere
  • 37
  • [ 1365692-79-0 ]
  • C69H47NOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 100 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 100 °C / Inert atmosphere
  • 38
  • [ 1365692-79-0 ]
  • C24H27Br2N3 [ No CAS ]
  • C54H53N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.5% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; for 24h; 4 Intermediate Synthesis Example 4: Synthesis of Intermediate (5) In a 1-neck 250 mL flask, 3.2 g (6.2 mmol) of Intermediate (3), 5.2 g (16.2 mmol) of Intermediate (1), 40.7 g (0.6 mmol) of Pd(PPh3), 15 mL of ethanol, 31 mL of toluene, and 318 mL of 2M K2CO (37.5 mmol) was added and stirred at 85 °C for throughout the day. After completion of the reaction, extraction was performed with EA, water was removed with MgSO 4 , and the solvent was removed by distillation under reduced pressure. Purification was performed by SiO2 column chromatography (EA:HEX). 4.2 g (yield: 90.5%) of the compound (intermediate (5)) as a beige solid was obtained.
  • 39
  • [ 1365692-79-0 ]
  • C24H27Br2N3 [ No CAS ]
  • C54H51N3Pt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol / 24 h / 85 °C 2: benzonitrile / 24 h / 190 °C
  • 40
  • [ 1365692-79-0 ]
  • C30H32BrN3 [ No CAS ]
  • C45H45N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54.6% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; for 24h; 3 Intermediate Synthesis Example 3: Synthesis of Intermediate (4) In a one-necked 500 mL flask, 4.9 g (9.5 mmol) of Intermediate (3), 4.6 g (14.2 mmol) of Intermediate (1), 1.1 g (0.9 mmol) of Pd(PPh3)4, 23 mL of ethanol,Toluene (47 mL) and 2M K2CO3 (23 mL (47.3 mmol)) were added, and the mixture was stirred at 80°C throughout the day.After completion of the reaction, extraction was performed with EA, water was removed with MgSO 4 , and the solvent was removed by distillation under reduced pressure. Purification was performed by SiO2 column chromatography (EA:HEX). It was further purified by SiO2 column chromatography (EA:HEX). 2.4 g (yield: 54.6%) of the compound (intermediate (4)) as a pale yellow solid was obtained.
  • 41
  • [ 1365692-79-0 ]
  • C30H32BrN3 [ No CAS ]
  • C45H43N3Pt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol / 24 h / 80 °C 2: benzonitrile / 3 h / 190 °C
  • 42
  • [ 1365692-79-0 ]
  • C33H20ClN3S [ No CAS ]
  • C48H33N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
57.7% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In water; toluene for 16h; Reflux; Inert atmosphere; 1.3 Step 3 Intermediate 2 Intermediate 1 Compound 1 A 250 ml three necked round-bottomed flask with magnetic stirrer, thermometer and re flux condenser was charged with Intermediate 2 (3.0 g, 5.70 mmol), Intermediate 1 (2.009 g, 6.27 mmol), tetrabutylammonium bromide (0.092 g, 0.285 mmol) and K2CO3 (2.364 g, (0493) 17.11 mmol), followed by Toluene (120 ml) and Water (30 ml). The reaction mixture was evacu ated three times and flushed with nitrogen. Afterwards nitrogen was bubbled through the reaction mixture for 30 minutes, before Pd(PPh3)4 (0.330 g, 0.285 mmol) was added. The yellow suspension was stirred at reflux for 16 hours. The brown solution was filtered through a pad of silica and washed with Toluene. The Toluene phase was washed with water, dried over Mg2SC>4 and concentrated to give 4.78 g of a brown oil. (0494) The product was purified by chromatography using Heptane/ Methylene Chloride = 9:1 as eluent followed by crystallization from Cyclohexane to yield 2.37 g (57.7% of theory) of Compound 1 as a white solid. (0495) 1H NMR (300 MHz, Methylene Chloride- (0496) 0.8 Hz, 2H), 7.59 - 7.46 (m, 6H), 7.46 - 7.39 (m, 1H), 7.35 (td, J= 7.5, 1.1 Hz, 1H), 7.16 (ddd, J = 7.9, 7.3, 1.3 Hz, 1H), 1.59 (s, 6H).
  • 43
  • [ 855837-58-0 ]
  • [ 1365692-79-0 ]
  • [ 2798001-72-4 ]
YieldReaction ConditionsOperation in experiment
64% With tetrakis-(triphenylphosphine)-palladium; tetrabutylammonium bromide; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 80℃; for 12h; Inert atmosphere; 2 Synthesis of intermediate 1-Ref-2: In a 25 ml three-necked flask, add raw material 10 (1 mmol),Starting material 11 (1 mmol), tetrakis(triphenylphosphine)palladium (0.05 mmol),Tetrabutylammonium bromide (0.05mmol), sodium carbonate (1.5mmol), toluene 10ml,Ethanol (2 mL), water (2 mL), the system was heated to 80 degrees Celsius, and reacted for 12 hours,After the reaction was completed, the system was cooled to room temperature, water was added, and extracted with ethyl acetate.The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed,The crude product was separated by column chromatography (ethyl acetate/n-hexane, 1/10 (volume ratio)),Intermediate 1-Ref-2 was obtained (0.23 g, 64% yield).
  • 44
  • [ 1365692-79-0 ]
  • [ 2798001-74-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis-(triphenylphosphine)-palladium; tetrabutylammonium bromide; anhydrous sodium carbonate / ethanol; toluene; lithium hydroxide monohydrate / 12 h / 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / 180 °C / Inert atmosphere 3: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl [2’,4’,6’-tris(propan-2-yl)-[1,1‘-biphenyl]-2-yl]phosphane / toluene / 12 h / Inert atmosphere; Reflux
  • 45
  • [ 1365692-79-0 ]
  • [ 2798001-73-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium; tetrabutylammonium bromide; anhydrous sodium carbonate / ethanol; toluene; lithium hydroxide monohydrate / 12 h / 80 °C / Inert atmosphere 2: triphenylphosphine / 1,2-dichloro-benzene / 12 h / 180 °C / Inert atmosphere
  • 46
  • [ 1365692-79-0 ]
  • [ 1954688-65-3 ]
  • [ 1955546-00-5 ]
YieldReaction ConditionsOperation in experiment
54 % With palladium diacetate; caesium carbonate; XPhos In ethanol; water; toluene Heating; 12 [Synthesis Example 12] Synthesis of Compound 129 3.0 g of Py-5 synthesized in Preparation Example 5, 2.8 g of 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan, and 3.0 g of Cs2CO3 were mixed, 60 ml of toluene, 12 ml of ethanol, and 12 ml of water were added thereto, and 55 mg of Pd(OAc)2 and 250 mg of Xphos were further added thereto, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and then filtered. A filtrate was poured into water, an organic layer was extracted with methylene chloride, and the organic layer was dried over MgSO4. The dried organic layer was concentrated under reduced pressure and then columned with THF:Hex=1:3, and thus Compound 129 (2.1 g, yield: 54%) was prepared. (0143) Mass: [(M+H)+]: 578
  • 47
  • [ 1365692-79-0 ]
  • [ 2165329-64-4 ]
  • [ 1955545-97-7 ]
YieldReaction ConditionsOperation in experiment
54 % With palladium diacetate; caesium carbonate; XPhos In ethanol; water; toluene Heating; 3 [Synthesis Example 3] Synthesis of Compound 29 3.0 g of Py-2 synthesized in Preparation Example 2, 2.8 g of 2-(9,9-dimethyl-9H-fluoren-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan, and 3.0 g of Cs2CO3 were mixed, 60 ml of toluene, 12 ml of ethanol, and 12 ml of water were added thereto, and 55 mg of Pd(OAc)2 and 250 mg of Xphos were further added thereto, and the mixture was heated and stirred for 4 hours. After the reaction was completed, the temperature was lowered to room temperature and then filtered. A filtrate was poured into water, an organic layer was extracted with methylene chloride, and the organic layer was dried over MgSO4. The dried organic layer was concentrated under reduced pressure and then columned with MC:Hex=1:2, and thus Compound 29 (2.3 g, yield: 54%) was prepared. (0116) Mass: [(M+H)+]: 654
  • 48
  • [ 1365692-79-0 ]
  • [ 2925910-86-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 5 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 5 h / 100 °C / Inert atmosphere 3: bis(dibenzylideneacetone)-palladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 12 h / 100 °C / Inert atmosphere
  • 49
  • [ 1365692-79-0 ]
  • [ 2925912-00-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 5 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane; water / 5 h / 100 °C / Inert atmosphere
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