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[ CAS No. 1021306-45-5 ]

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Chemical Structure| 1021306-45-5
Chemical Structure| 1021306-45-5
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CAS No. :1021306-45-5 MDL No. :MFCD16294551
Formula : C19H19BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :306.16 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1021306-45-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1021306-45-5 ]

  • Downstream synthetic route of [ 1021306-45-5 ]

[ 1021306-45-5 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 738580-13-7 ]
  • [ 1021306-45-5 ]
  • [ 1021306-50-2 ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In toluene Heating;
  • 2
  • [ 3096-56-8 ]
  • [ 73183-34-3 ]
  • [ 1021306-45-5 ]
YieldReaction ConditionsOperation in experiment
84.6% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 24h; Reflux;
71% With potassium acetate In N,N-dimethyl-formamide at 60℃; for 18h;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere; 8.1 Step 2 Preparation of 4-(4,4,5,5-tetramethyl-1,3,2-dioxapentaneborane)-9-ethyl-9H-carbazole General procedure: The step 1 was obtained by weighing 4-chloro-9-ethyl-9H-carbazole (1 mmol), boronic acid pinacol ester (1.1 mmol), potassium acetate (2 mmol) and1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl2, 2 mmol) in a reaction flask, 5 mL of 1,4-dioxane, 100 ° C under nitrogen atmosphere After reacting for 24 hours, after the reaction was completed, water was added and ethyl acetate was extracted.The organic phase was combined, washed with brine brine, brinePurification by column chromatography gave the title compound.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere; 4.1 Step 1 Preparation of 2-(4,4,5,5-tetramethyl-1,3,2-dioxapentaneborane)-9-fluorenone Take 2-bromo-9-fluorenone (1 mmol), boronic acid pinacol ester (1.1 mmol),Potassium acetate (2 mmol) and 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl2, 2 mmol) were placed in a reaction flask, and 5 mL of 1,4-dioxane was added. the reaction was carried out at 100 °C for 24 h under a nitrogen atmosphere. After the reaction was completed, water was added, ethyl acetate was evaporated, and the organic phase was combined, washed with brine, and the organic phase was combined, dried, filtered, concentrated and purified by column chromatography.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere; 4.1 step 1 Preparation of 2-(4,4,5,5-tetramethyl-1,3,2-dioxapentaneborane)-9-fluorenone Take 2-bromo-9-fluorenone (1mmol),bis(pinacolato)diboron(1.1mmol),Potassium acetate (2 mmol) and 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride(Pd(dppf)Cl2, 2 mmol) in a reaction flask, 5 mL of 1,4-dioxane was added.The reaction was carried out at 100 ° C for 24 h under nitrogen protection. After the reaction was over, water was added.The organic phase was combined, washed with saturated brine, and the organic phases were combined and dried.Filter, concentrate and purify by column chromatography.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere; 4.1 step 1 2-(4,4,5,5-tetramethyl-1,3,2-dioxapentane borane-9-fluorenone Preparation Take 2-bromo-9-fluorenone (1mmol),Boronic acid pinacol ester (1.1mmol),Potassium acetate (2mmol)And 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl2, 2 mmol)In the reaction bottle,Add 5mL of 1,4-dioxane,Reacting at 100 ° C for 24 h under nitrogen protection conditions,After the reaction,Add water and extract with ethyl acetate.Combine the organic phase,Washed with saturated saline,Combine the organic phase,Dry, filter,Concentrated and purified by column chromatography.

  • 3
  • [ 1021306-45-5 ]
  • [ 1008788-37-1 ]
  • [ 1361061-22-4 ]
YieldReaction ConditionsOperation in experiment
67% With tetrakis(triphenylphosphine) palladium(0) In toluene at 90℃; for 24h; Inert atmosphere;
  • 4
  • [ 1021306-45-5 ]
  • [ 885-39-2 ]
  • 2,2′-((9H-fluoren-9-ylidene)methylene)bis(9H-fluoren-9-one) [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.5% With tetrakis(triphenylphosphine) palladium(0); tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In water; toluene at 90℃; Inert atmosphere;
  • 5
  • [ 1021306-45-5 ]
  • [ 2592-73-6 ]
  • C40H24O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.3% With tetrakis(triphenylphosphine) palladium(0); tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In water; toluene at 90℃; Inert atmosphere;
  • 6
  • [ 1021306-45-5 ]
  • [ 214779-03-0 ]
  • C68H36O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.8% With tetrakis(triphenylphosphine) palladium(0); tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In water; toluene at 90℃; Inert atmosphere;
  • 7
  • [ 1021306-45-5 ]
  • 2,2′-((9H-fluoren-9-ylidene)methylene)bis(9H-fluoren-9-one) [ No CAS ]
  • C94H50O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In water; toluene at 90℃; Inert atmosphere;
  • 8
  • [ 1021306-45-5 ]
  • C42H24Br4 [ No CAS ]
  • C94H52O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.5% With tetrakis(triphenylphosphine) palladium(0); tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In water; toluene at 90℃; Inert atmosphere;
  • 9
  • [ 1021306-45-5 ]
  • [ 57102-97-3 ]
  • C27H19NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium fluoride; tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; toluene at 90℃; for 0.5h; Inert atmosphere; 4 Example implementation 4, With KF and K2CO3 2mol / L mixed solution A50mL,VTHF: VTol = 1: 1 mixture of 50mL,A, B solution N2 bubbling 2h.Two flasks,Magnetic,Condenser assembly,Seal system only add sample port.A mixture of the starting 3-bromo-9-ethylcarbazole (10 g, 36.48 mmol),Fluorenone boronic acid ester, compound 4 (11.16 g, 36.48 mmol)And tetrakistriphenylphosphine palladium (0.2 g, 0.18 mol)Was added to the flask,Sealing system,And the reaction bottle wrapped with tin foil.Vacuum 2-3 times to inject organic phase B into the reaction flask.90 oil bath stirring heating reaction,30min at35 mL of aqueous solution A was added.The reaction was stirred.At the end of the reaction,50 mL of water was quenched,The organic layer was extracted using CH2Cl2,The organic phases were combined,Dried over anhydrous sodium sulfate,The solvent was removed by rotary evaporation,Column chromatography separation and purificationBrownYellow solid powderCompound 5 (9.5 g, 70%)
  • 10
  • [ 1021306-45-5 ]
  • [ 3096-56-8 ]
  • C32H14N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 15 h / Inert atmosphere; Reflux 2: pyridine; titanium tetrachloride / chlorobenzene; dichloromethane / 10 h / Inert atmosphere
  • 11
  • [ 1021306-45-5 ]
  • [ 3096-56-8 ]
  • [ 95868-98-7 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 15h; Inert atmosphere; Reflux; 1 Synthesis of Compound A To a 250 ml round bottom flask was added 2-bromo-9H-fluoren-9-one (5.0 g, 19.3 mmol), 2- (4,4,5,5- Tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-fluorene-9-one (2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl) -9H-fluoren-9-one (6.5 g, 21.2 mmol) was dissolved in 150 ml of tetrahydrofuran (THF), tetrakis (triphenylphosphine) palladium (PPh3) 4) (0.45 g, 0.39 mmol) and 30 ml of a 2M potassium carbonate (K2CO3) aqueous solution were added thereto, and the mixture was refluxed under argon atmosphere for 15 hours. After completion of the reaction, the solution was distilled under reduced pressure to remove tetrahydrofuran, extracted with ethyl acetate, and then the organic material was distilled off under reduced pressure. Compound A-1 was isolated from the residue by column chromatography.
YieldReaction ConditionsOperation in experiment
88% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 60℃; for 22h; Inert atmosphere; 21 Synthesis of compound 1 General procedure: A mixture of 2-bromofluorene (0.74 g, 3.0 mmol), bis(pinacolato)diboran (1.22g, 4.8 mmol) and KOAc (0.88 g, 9.0 mmol) in DMF (30 ml) was de-aerated with argon.After an addition of [1 ,1 '-bis(diphenylphosphine)ferrocene] dichloropalladium ( 11) complex with CH2CI2 (0.12 g, 0.15 mmol), the reaction m ixture was stirred at 60°C for 22 h. Water (30 ml) was added, the mixture was extracted with Et20 (50 ml + 20 ml), and the combined organic phases were dried with Na2S04. The productwas purified by FC (silica gel, 20% EtOAc in petroleum ether (b.p. 40-65 °C)). Yield: 0.88 g (100%).
  • 13
  • [ 1021306-45-5 ]
  • [ 120491-89-6 ]
  • C44H57N3O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethylene glycol; N,N-dimethyl-formamide at 85℃; for 6h; Inert atmosphere; 29 Synthesis of compound 23 A mixture of the compound 18 (0.17 g, 0.50 mmol), tetra( ferf-butyl) 2,2',2",2"'-[(4-bromopyridine-2,6-diyl)bis(methylenenitrilo)]tetrakis(acetate) (0.22 g, 0.33 mmol),CsC03 (0.18 g, 0.56 mmol) in dry DMF (1.4 ml) and 1 ,2-ethanediol (1.4 ml) was de- aerated with argon. After addition of tetrakis(triphenylphosphine)palladium (8mg, 6.6 μηοΙ), the mixture was stirred for 1 h at 85 °C. The mixture was dissolved in CH2CI2 (30 ml), washed with H20 (3 x 10 ml) and dried with Na2S04. Theproduct was purified by FC (silica gel, first from 40% to 50% EtOAc in petroleum ether (b.p. 40-65 °C), then 50% EtOAc in petroleum ether (b.p. 40-65 °C) including10% triethylam ine) . Yield: 80 mg (32%).
  • 14
  • [ 1021306-45-5 ]
  • 5''-bromo-3-octyl-2,2':5',2''-terthiophene [ No CAS ]
  • 2-(3''-octyl-[2,2':5',2''-terthiophen]-5-yl)-9H-fluoren-9-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.3% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In water; toluene at 110℃; for 30h; Inert atmosphere;
  • 15
  • [ 1021306-45-5 ]
  • 5''-bromo-3-octyl-2,2':5',2''-terthiophene [ No CAS ]
  • (E)-2,2'-bis(3''-octyl-[2,2':5',2''-terthiophen]-5-yl)-9,9'-bifluorenylidene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate / toluene; water / 30 h / 110 °C / Inert atmosphere 2: Lawessons reagent / toluene / Inert atmosphere; Reflux
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