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(10-([1,1'-biphenyl]-4-yl)-anthracene-9-yl)boronic acid[ No CAS ]
[ 7351-74-8 ]
C62H40[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
70%
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux;
4-F. Preparation of compound 4; [128] Under N atmosphere, <strong>[7351-74-8]1,5-<strong>[7351-74-8]dibromonaphthalene</strong></strong> (1 g, 3.6 mmol), the compound 4e(3.0 g, 8.02 mmol) and Pd(PPh ) (0.2 g, 0.18 mmol) were added to a 2 M aqueous3 4 solution of potassium carbonate (100 mL) and anisole (100 mL). The mixture was refluxed under stirring for about 24 hours. After completing the reaction, the mixture was cooled to normal temperature. The organic layer was separated from the reaction mixture, and filtered to obtain a solid. The solid was recrystallized from THF and EtOH to prepare a compound 4 (2.0 g, 70%). MS [M] = 784
(10-([1,1'-biphenyl]-4-yl)-anthracene-9-yl)boronic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
Stage #1: 9‐[1,1'‐biphenyl]‐4‐yl}‐10‐bromoanthracene With n-butyllithium In diethyl ether; hexane; toluene at -64℃; for 2.5h;
Stage #2: In diethyl ether; hexane; toluene at 20℃; for 12.25h;
Stage #3: With hydrogenchloride; water In diethyl ether; hexane; toluene at 0 - 10℃;
4.4-E
4-E. Preparation of compound 4e; [126] Under N atmosphere, to a compound 4d (7 g, 17.1 mmol), dehydrated ether (80 mL) and dehydrated toluene (80 mL) were added, and cooled to -640C in ice bath. A 2.5 M butyl lithium/hexane solution (9 mL) was added dropwise thereto for 30 minutes, and subjected to reaction at -640C for 2 hours. Boronic acid triisoester (12 mL) was added dropwise thereto for 15 minutes, and then stirred at room temperature for 12 hours. After ice cooling, 2 N hydrochloric acid (70 mL) was added at 1O0C or lower and toluene (30 mL) was added. The mixture was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from hexane to prepare a yellow solid. To the solid, cone, hydrochloric acid (7 mL) and tetrabutylammonium bromide (0.04 g, 0.1 mmol) were added, and dissolved in THF (100 mL). The mixture was subjected to reaction at room temperature for 12 hours. After completing the reaction, the mixture was solidified in H O and filtered to prepare a compound 4e (3.2 g, 50%).
With bis(tri-t-butylphosphine)palladium(0); potassium carbonate In tetrahydrofuran; water for 4h; Reflux;
1 Preparation of Formula 1-2
[Formula2-A] (15g, 55.8mmol) and (10 - ([1,1'-biphenyl] -4-yl) -anthracene-9-yl)boronic acid (20.1g, 55.8mmol) was added in 200mL THF. It was added K2CO3 23g dissolved in water70mL.After In the Pd (Pt-Bu3) 2 0.3g was stirred and refluxed for 4 hours, Aftercooling to room temperature the resulting solids were filtered.The filteredsolid was recrystallized in ethanol to conduct the chloroform was prepared [Formula 1-2] (22.3g, yield 71%).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 4h; Reflux;
9 Preparation of [Formula 2-2]
[Formula 2-E] (10g, 33.3mmol) and (10 -([1,1'-biphenyl] -4-yl) anthracene-9-yl) boronic acid ((10 - ([1,1; biphenyl] -4-yl)anthracen-9-yl) a boronic acid) (12.5g, 33.3mmol) was placed in 100mL THF.K2CO3 14g was put anddissolved in 30mL H2O.After injectingthe Pd (PPh3) 4 0.8g was stirredand refluxed for 4 hours.After cooling to room temperature, filtered.Thefiltered solid wasrecrystallized with chloroform and ethanol [Formula 2-2] (13.5g, yield 74%) was prepared
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 4h; Reflux;
4 Preparation of Formula 1-6
[Compound B-2] (15g, 38.1mmol) and (10 - ([1,1'-biphenyl] -4-yl) anthracene-9-yl) boronic acid ((10 - ([1,1 & ' biphenyl] -4-yl) anthracen-9-yl) were charged to the boronic acid) (15.0g, .0mmol), THF 100mL. In the K2CO316g it was dissolved in water 50mL. After the input of the catalyst Pd (PPh3) 4 0.9g was stirred and refluxed for 4 hours. After cooling to room temperature the resulting solids were filtered. The filtered solid was recrystallized with chloroform and ethanol, filtered, back, and dried to prepare a [Formula 1-6] (14.0g, 75% yield).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 4h; Reflux;
2 Preparation of [Formula 1-2]
[Compound 2-A] (10g, 31.7mmol) and (10 - ([1,1'-biphenyl] -4-yl) anthracene-9-yl) boronic acid ((10 - ([1,1 & ' biphenyl] -4-yl) anthracen-9-yl) were charged to the boronic acid) (12.5g, 33.3mmol), THF 100mL. In the K2CO313g it was dissolved in water 50mL. After the input of the catalyst Pd (PPh3) 4 0.7g was stirred and refluxed for 4 hours. After cooling to room temperature the resulting solids were filtered. The filtered solid was recrystallized with chloroform and ethanol, filtered, back, and dried to prepare a [Formula 1-2] (13.8, 77% yield).
With potassium phosphate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In 1,4-dioxane; water for 8h; Reflux;
4 Example 4: preparation of Compound 20
[Compound E] (10 g, 29.9 mmol) and [Compound F] (9.1, 29.9 mmol) were placed in 150 mL of dioxane. 100 ml of 2M K3PO4, 0.5 g of Pd (dba) 2 and 0.5 g of PCy3 were added, and the mixture was refluxed for 8 hours. After cooling to room temperature, the reaction mixture was filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 20] (13.4 g, yield 75%
With potassium phosphate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In 1,4-dioxane; water for 10h; Reflux;
6 Example 6: preparation of Compound 35
[Compound E] (10 g, 29.9 mmol) and [Compound H] (11.9 g, 29.9 mmol) were added to 150 mL of dioxane. 100 ml of 2M K3PO4, 0.5 g of Pd (dba) 2 and 0.5 g of PCy3 were added, and the mixture was refluxed for 10 hours. The reaction mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to obtain [Compound 35] (14.0 g, yield 68%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 85℃; Inert atmosphere;
4.5
Under N2 protection, 9-(2-biphenyl)indole-10 boronic acid (43.12 g 160 mmol), 2-([1,1'-biphenyl]-4-yl)-6 was added to a 1000 mL three-neck flask. Bromo-1-methoxy-benzimidazole (39.47 g 148 mmol), tetrakistriphenylphosphine palladium (0.92 g 0.8 mmol), 2M potassium carbonate solution (160 mL), toluene (320 mL), ethanol (160 mL), at 85 °C, heated backThe reaction was allowed to proceed overnight. The reaction was monitored by TLC. After the reaction was completed, deionized water was added and extraction was performed three times with dichloromethane. The organic layer was collected and the organic liquid was removed over anhydrous magnesium sulfate. The white product was obtained by column chromatography. SET -467g, yield: 83%.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 8h; Inert atmosphere; Reflux;
1
In a 2000mL three-necked bottle, under the protection of nitrogen,Add 300mL toluene, 300mL ethanol, 100mL water, add 37.4g (0.1mol) 9- (4-phenylphenyl) -anthracene-10-boronic acid, 15.7g (0.1mol) p-chloronitrobenzene, 5.78g with stirring (0.005mol) tetrakis (triphenylphosphine) palladium and 27.6g (0.2mol) potassium carbonate, slowly heated to reflux for 8h, cool down, add water solution, concentrate the organic layer to dryness,Recrystallized with a mixed solvent of ethanol and toluene,A total of 39.6 g of intermediate M1-1 was obtained as a yellowish solid with a yield of 87.8%.
87.8%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 8h; Inert atmosphere; Reflux;
1.1 (1) Synthesis of the compound represented by M-1:
In a 2000 ml three-necked bottle, under the protection of nitrogen, add 300 ml of toluene,300 ml of ethanol,100 ml of water, with stirring, add 37.4 g (0.1 mol) of 9-(4-phenylphenyl)-anthracene-10-boronic acid represented by M-0, 15.7 g (0.1 mol) of p-chloronitrobenzene,5.78g (0.005mol) tetrakis(triphenylphosphine) palladium, 27.6g (0.2mol) potassium carbonate,Slowly heated to reflux for 8 hours,Cool down, add water, concentrate the organic layer to dryness, and recrystallize it with a mixed solvent of ethanol and toluene to obtain the compound represented by M-1 as a yellowish solid, weight 39.6 g, yield 87.8%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 90℃; for 12h; Inert atmosphere;
2 2) Synthesis of A01
Under nitrogen atmosphere2-(4-(4-bromophenyl)-6-(pyrazin-2-yl)pyridin-2-yl)pyrazine(2-(4-(4-bromophenyl)-6-(pyrazin-2-yl)pyridin-2-yl)pyrazine) (5g 12.8mmol), [10-(4-biphenylyl)-9-anthryl ]Boronic acid ([10-(4-Biphenylyl)-9-anthryl]boronic acid) (5.27g 14.1mmol), tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4) (0.44g 0.384 mmol), 4M potassium carbonate (K2CO3) (10ml), 30ml of toluene, and 10ml of ethanol were added and stirred under reflux for 12 hours. After the reaction was completed, 50 ml of water (H2O) was added, stirred for 3 hours, filtered under reduced pressure, and recrystallized from methylene chloride (MC) to obtain compound A01 (6.9 g, yield 84.6%).
With palladium diacetate; sodium carbonate; XPhos In ethanol; water; toluene at 50 - 90℃; for 16h;
5 Synthesis example 5
Compound I-1-c (5.0 g, 13.63 mmol), 10-(4-biphenyl)-9-anthraceneboronic acid (8.0 g, 18.38 mmol) and toluene (150 mL) were added to a 250 mL double-necked reaction flask, After stirring and heating to 50°C, add palladium acetate (0.15g, 0.67mmol) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.35g, 0.73mmol), and stir. After homogenization, ethanol (50 ml) was added first, and then 2.0 M sodium carbonate aqueous solution (60 ml) was added dropwise, and the temperature was raised to 90° C. for 16 hours. After the system was cooled to room temperature, the solid was collected by filtration and rinsed with additional toluene (150 ml). The collected crude product solid was placed in a 250 ml beaker and toluene (120 ml) was added, heated and stirred until dissolved. Filter with diatomaceous earth and silica gel while hot, and then concentrate the collected filtrate, and then crystallize the solid with toluene and hexane to obtain compound I-5 as a pale yellow solid (3.8 g, yield 42%)
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 85℃; for 10h; Inert atmosphere;
1.4 Step 4. Synthesis of compound 2
[Intermediate 1-c] (2.5g, 8.6mmol), 10-([1,1'-biphenyl]-4-yl)anthracene-9-ylboronic acid (3.24g, 8.6mmol),Tetratriphenylphosphine palladium (520mg, 0.46mmol) and potassium carbonate (2.50g, 18.7mmol) were added to a 250mL three-necked round bottom flask,Then, 45 mL of tetrahydrofuran and 5 mL of water were added. The reaction flask was heated to 85°C and refluxed, and stirred for 10 hours under a nitrogen atmosphere.After the reaction, the reaction system was cooled to room temperature and extracted with dichloromethane,The organic phase was dried and concentrated and separated by column chromatography to obtain a pale yellow solid compound 2 (1.7 g, 3.2 mmol, 37.2%). The product was confirmed to be the target product with a molecular weight of 539.2.
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In water; toluene Inert atmosphere; Reflux;
Synthesis Example (A-4): Synthesis of Compound (1-4)
Under a nitrogen atmosphere, 9-biphenyl-10-anthracene boronic acid (20.0 g) synthesized by a known method was dissolved in toluene (400 ml), and 1-bromo-7-chlorodibenzofuran (12.4 g) thereto , potassium carbonate (12.2 g), tetrabutylammonium bromide (0.12 g), dichlorobis(triphenylphosphine)palladium(II) (1.5 g) and water (50 ml) were added, and stirring was performed under heating and reflux for 3 hours.After the reaction, water and toluene were added to the reaction solution, and the organic layer was separated and washed with water.After that, the organic layer was concentrated to obtain a crude product.The crude product was purified with a silica gel column (eluent: toluene) to obtain an intermediate (IC) (14.1 g).
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; Inert atmosphere;
1.2-1.3 Step 2: the preparation of compound TPOAN-DP
Under N2 atmosphere, tetrakis(triphenylphosphine)palladium (32mg, 0.028mmol) was added to (10-([1,1'-biphenyl]-4-yl)anthracen-9-yl)boronic acid (1.35g , 3.6mmol), (3-bromophenyl)diphenylphosphine oxide (1g, 2.8mmol), sodium carbonate aqueous solution (2M, 8.4mmol), toluene (40mL), ethanol (9mL) in the reaction solution.The reaction was heated to 100°C and stirred overnight. After cooling to room temperature, water was added, the organic layer was separated, and back-extracted with water.The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure and separated by column chromatography. The eluent was a mixed solvent of dichloromethane and ethanol; for the sample separated by column chromatography, or further use alcohols Solvent washing gave a white solid (1.2g).
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