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[ CAS No. 334658-75-2 ] {[proInfo.proName]}

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Chemical Structure| 334658-75-2
Chemical Structure| 334658-75-2
Structure of 334658-75-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 334658-75-2 ]

CAS No. :334658-75-2 MDL No. :MFCD11111989
Formula : C20H15BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :RVPCPPWNSMAZKR-UHFFFAOYSA-N
M.W : 298.14 Pubchem ID :22247164
Synonyms :

Calculated chemistry of [ 334658-75-2 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 20
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 96.72
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 4.95
Log Po/w (WLOGP) : 3.34
Log Po/w (MLOGP) : 3.48
Log Po/w (SILICOS-IT) : 2.95
Consensus Log Po/w : 2.94

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.32
Solubility : 0.00143 mg/ml ; 0.0000048 mol/l
Class : Moderately soluble
Log S (Ali) : -5.54
Solubility : 0.000865 mg/ml ; 0.0000029 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.15
Solubility : 0.0000213 mg/ml ; 0.0000000714 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.36

Safety of [ 334658-75-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 334658-75-2 ]

* 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 [ 334658-75-2 ]

[ 334658-75-2 ] Synthesis Path-Downstream   1~24

  • 1
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 95962-62-2 ]
  • C58H38 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With sodium carbonate In 1,2-dimethoxyethane; water for 8h; Heating / reflux;
  • 2
  • [ 334658-75-2 ]
  • [ 952604-26-1 ]
  • [ 944801-50-7 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate In water; methoxybenzene for 24h; Heating / reflux; 26.26-B 26-B. Preparation of compound 85; [277] Under N atmosphere, a compound 26a (1 g, 2.8 mmol) prepared in 26-A,10-phenyl anthracene-9-boronic acid (3.8 g, 6.1 mmol), and Pd(PPh ) (0.16 g, 0.143 4 mmol) were added to a 2 M aqueous solution of potassium carbonate (20 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, filtered to obtain a solid. The solid was recrystallized from THF and EtOH to prepare a compound 85 (1.5 g, 75%). MS [M] = 708
70% With sodium carbonate In 1,2-dimethoxyethane; water for 7.5h; Heating / reflux; 1 Synthesis Example 1 (Synthesis of a compound (AN-1)) ; Under the atmosphere of argon, 10 g of 1-bromo-4-iodonaphthalene and 6 g of 4-bromophenylboronic acid which were synthesized in accordance with conventional processes were dissolved into 150 ml of toluene, and 45 ml of a 2M aqueous solution of sodium carbonate was added. Then, 1 g of tetrakistriphenylphosphinepalladium was added, and the resultant mixture was heated under the refluxing condition for 7 hours. After one night, the formed organic layer was extracted with toluene, washed with water and a saturated aqueous solution of sodium chloride. The organic layer was dried with anhydrous sodium sulfate, and the solvent was removed by distillation. The residue was purified in accordance with the silica gel column chromatography (the solvent of development: toluene/hexane), and 6.3 g of 1-bromo-4-(4-bromophenyl)-naphthalene was obtained (the yield: 58%). The obtained 1-bromo-4-(4-bromophenyl)naphthalene in an amount of 6 g was mixed with 10 g of 10-phenylathracene-9-boronic acid synthesized in accordance with a conventional process and 150 ml of DME. Then, 1.1 g of tetrakistriphenylphosphinepalladium and 50 ml of a 2M aqueous solution of sodium carbonate were added, and the atmosphere was purged with argon. After the resultant mixture was heated under the refluxing condition for 7.5 hours, the mixture was cooled by leaving standing, and formed crystals were separated by filtration. The separated crystals were washed with water, methanol and then heated toluene, and 8.3 g of the object compound (AN-1) was obtained as a light yellow solid substance (the yield: 70%). When the obtained compound was examined in accordance with the field desorption mass spectroscopy (FDMS), it was found that m/z=708, which agreed with C56H36=708, and the above compound was identified to be Compound AN-1.
  • 3
  • [ 334658-75-2 ]
  • [ 394737-28-1 ]
  • [ 1262129-42-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / 24 h / Inert atmosphere; Reflux 2: boron tribromide / dichloromethane / 0 °C
  • 4
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 106-37-6 ]
  • [ 625854-02-6 ]
YieldReaction ConditionsOperation in experiment
51% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 18h; Inert atmosphere; 2 Synthesis of Compound (1-11) Under an argon stream, 3.58 g (12.0 mmol) of the compound (1-10) synthesized by the above reaction, 11.32 g (48.0 mmol) of 1,4-dibromobenzene and 0.28 g (0.24 mmol) of tetrakis (triphenylphosphine) palladium (0) were dissolved in 80 ml of toluene and 10 ml of ethanol. Then, 18 ml of an aqueous solution containing 36.0 mmol of sodium carbonate was added, and the mixture was stirred under reflux for 18 hours. After cooling to room temperature, water was added to the reaction solution and extracted with toluene. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by column chromatography and a white solid (yield 2.50 g, yield 51%) of the target compound (1-11) was obtained.
43.8% With sodium carbonate In ethanol; water; toluene at 90℃; for 12h; 3 Synthesis of 9-phenyl-10-(4-bromophenyl)anthracene Exemplary Synthesis 3; Synthesis of Compound 3; Synthesis of 9-phenyl-10-(4-bromophenyl)anthracene; An amount of 2.46 g (8.26 mmol) of 10-phenylanthracene-9-boronic acid synthesized in the same manner as in Exemplary Synthesis 2, 9.75 g (41.3 mmol) of p-dibromobenzene, and 250 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 60 ml of toluene and 15 ml of ethanol. Then, 30 ml of 2M sodium carbonate solution was added and allowed to react at 90° C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 1.48 g (3.62 mmol) of 9-phenyl-10-(4-bromophenyl)anthracene. The yield was 43.8%. Synthesis of 7,12-Diphenylbenzofluoranthene-9-Boronic Acid; An amount of 3 g (6.21 mmol) of 9-bromo-7,12-diphenylbenzofluoranthene synthesized in the same manner as in Exemplary Synthesis 1 was dissolved in dehydrated THF and cooled to -80° C. Then, 4.3 ml (6.8 mmol) of a solution of n butyllithium in n-hexane was added dropwise. Forty minutes later, 1.81 g (12.4 mmol) of triethyl borate was added. After two-hour reaction, a diluted hydrochloric acid solution was passed and allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 1.51 g (3.37 mmol) of 7,12-diphenylbenzofluoranthene-9-boronic acid. The yield was 54.3%. (Synthesis of Compound 3); An amount of 1.38 g (3.37 mmol) of 9-phenyl-10-(4-bromophenyl)anthracene, 1.51 g (3.37 mmol) of 7,12-diphenylbenzofluoranthene-9-boronic acid, and 100 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 60 ml of toluene and 15 ml of ethanol. Then, 30 ml of 2M sodium carbonate solution was added and allowed to react at 90° C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 2.01 g (2.75 mmol) of Compound 3. The yield was 81.6%.The obtained Compound 3 was identified by the mass spectrum, infrared absorption spectrum, and NMR.
With sodium carbonate In ethanol; water; toluene at 120℃; for 2h; 17 Preparation Example 17; Preparation of Compound (117); Preparation of Compound (265); In toluene (200 mL) and ethanol (100 mL), dissolved were Compound (261) (7.1 g, 23.8 mmol), 1,4-dibromobenzene (6.2 g, 26.2 mmol) and tetrakispalladium (O) triphenylphosphine (Pd(PPh3)4) (2.8 g, 2.4 mmol). Aqueous 2M sodium carbonate solution (120 mL) was added to the solution, and the mixture was stirred at 120° C. under reflux for 2 hours. Then, the temperature was lowered to 25° C., and the reaction was quenched by adding distilled water (200 mL). The reaction mixture was extracted with ethyl acetate (100 mL), and the extract was dried under reduced pressure. Recrystallization from tetrahydrofuran (10 mL) and methanol (200 mL) gave the objective compound (265) (5.8 g, 14.3 mmol).
  • 5
  • [ 121-43-7 ]
  • [ 23674-20-6 ]
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% 10 L 4-neck round bottom flask intermediate 1-d 280g (0.84 mol) dissolved in 3000 mL of THF there by maintaining the temperature at -78C. 1.6 M n-BuLi 630 mL it was added dropwise slowly for 2 hours after stirring at the same temperature trimethylborate was added dropwise. Raise the temperature to room temperature, it was stirred for 12 hours. When complete the reaction 2N HCl was added. The organic layer was separated after neutralization was recrystallized from toluene to intermediate 1-e (228 g, 91%) was obtained.
91% In a 10-L 4-neck, round-bottom flask, Intermediate 4-d (280 g, 0.84 mol) and THF (3000 mL) were placed and maintained at -78 C. 1.6M n-BuLi (630 mL) was slowly added to the solution which was then stirred for 2 hrs. At the same temperature, B(OMe)3 was dropwise added. The temperature was elevated to room temperature before stirring for 12 hrs. After completion of the reaction, 2N HCl was added. The organic layer was separated, neutralized, and recrystallized in toluene to afford Intermediate 4-e (228 g, 91%).
91% 280 g (0.84 mol) of Intermediate 1-d and 3000 mL of THF were added to a 10 L four neck round bottom flask and then maintained at a temperature of -78 C. 630 mL of 1.6 M n-butyllithium (n-BuLi) was slowly added thereto in a dropwise-manner, agitated for 2 hours, and then B(OMe)3 was added thereto in a drop-wise manner at the same (substantially the same) temperature. The temperature thereof was increased to room temperature and then agitated for 12 hours. After agitating for 12 hours (or after completing the reaction), 2 N HCl was added thereto. An organic layer was separated therefrom, neutralized, and then recrystallized with toluene to obtain Intermediate 1-e (228 g, 91%).
76.7% <strong>[23674-20-6]9-phenyl-10-bromo-anthracene</strong> (13.4 g, 40 mmol) was dissolved in 110 mL THF. In the cooling state up to -78 was put in the n-BuLi (30 mL) slowly. At the end of the addition and then stirred for about 1 hour at -78 trimethyl borate (5.9 g, 56 mmol)It was put. After 1 hour stirring at -78 stirred at room temperature for about two hours and put in a 2 N HCl was adjusted to acidic. The solvent was then extracted with EA and obtained with hexane to give the 9-phenyl-10-anthracene boronic acid 9.2 g (yield 76.7%).
76.7% In a round bottom flask, 9-phenyl-10-bromoanthracene (26.8 g, 80 mmol) prepared in Synthesis Example 1-1-b was dissolved in 220 mL of THF. N-butyllithium (60 mL) was slowly added while cooling to -78 C. After the addition, the mixture was stirred at -78 C for about 1 hour, and trimethyl borate (11.8 g, 112 mmol) was added thereto. After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid solution was added to adjust acidity. Crystals were extracted with hexane, followed by extraction with EA, to obtain 18.4 g (yield 76.7%) of 9-phenyl-10-anthraceneboronic acid.
71% <Preparation Example 2-1> Preparation of the following Compound B-2 Compound B-1 (5.96 g, 17.9 mmol) was dissolved in tetrahydrofuran (100 mL), the temperature was decreased to -78C, and then 1.7 M tertiary-butyllithium (t-BuLi) (10.6 mL, 17.9 mmol) was slowly added thereto. The resulting mixture was stirred at the same temperature for 1 hour, trimethyl borate (B (OCH3)3) (3.72g, 35.8 mmol) was added thereto, and then the resulting mixture was stirred for 3 hours while slowly increasing the temperature to normal temperature. 2 N hydrochloric acid aqueous solution (30 mL) was added to the reaction mixture, and stirred at normal temperature for 1.5 hours. The produced precipitate was filtered and washed sequentially with water and ethyl ether, and then vacuum-dried. After drying, the precipitate was dispersed in ethyl ether, and the resulting mixture was stirred for 2 hours, filtered, and dried to prepare Compound B-2 (3.79 g, 71%). MS: [M+H] + = 299
69% Intermediate 12-b (12.0 g, 36 mmol) was dissolved in 100 mL of tetrahydrofuran. After cooling to -78 C. under a nitrogen atmosphere, n-butyllithium (24.76 mL, 40 mmol) was slowly added dropwise for 30 min. The mixture was stirred at the same temperature for 1 h. To the mixture was added dropwise trimethyl borate (4.5 g, 43 mmol) at the same temperature. The resulting mixture was stirred at room temperature overnight. The reaction solution was acidified by dropwise addition of 2 N hydrochloric acid. After 1 h stirring, the mixture was extracted with ethyl acetate and recrystallized from hexane, affording 7.5 g (yield 69%) of Intermediate 12-c.
Preparation of Compound (261); Under nitrogen atmosphere, Compound (260) (9.9 g, 29.8 mmol) was dissolved in tetrahydrofuran (200 mL), and the solution was chilled to -78 C. To the solution, slowly added dropwise was n-butyl lithium (n-BuLi, 2.5M in hexane) (15.5 mL, 38.7 mmol). After 30 minutes, trimethylborate (6.8 mL, 59.6 mmol) was added thereto, and the resultant mixture was slowly warmed to room temperature. After stirring at the same temperature for one day, aqueous 1N hydrochloric acid solution (100 mL) was added. The mixture was stirred for 30 minutes, and extracted from water (200 mL) and dichloromethane (200 mL). The extract was dried under reduced pressure and recrystallized from ethyl acetate (20 mL) and hexane (300 mL) to obtain the objective compound (261) (7.1 g, 23.8 mmol).
250ml round bottom flask was put in the Intermediate b-1> (12.0g, 36mmol) was dissolved into 100ml of tetrahydrofuran. The reaction solution was cooled road -78 under a nitrogen atmosphere. It was slowly added dropwise for 30 minutes n-butyllithium (24.76ml, 40mmol) to the cooled solution, which was stirred for 1 hour at the same temperature. Trimethylborate (4.5g, 43mmol) was added dropwise at the same temperature was stirred overnight at room temperature. It was acidified by dropwise addition of 2 normal hydrochloric acid to the reaction solution, which was stirred for 1 hour. Extraction with ethyl acetate was separated organic layer was concentrated under reduced pressure, crystallization was put in the n-hexane. To give a intermediates c-1>.

  • 6
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 83-53-4 ]
  • [ 1062556-32-4 ]
YieldReaction ConditionsOperation in experiment
84.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene; at 80℃; The [Reaction Scheme 12] [Formula 2-a] (5g, 0.012mol), [formula b-2] (6.64g, 0.014mol) obtained from,Tetrakis (triphenylphosphine) palladium (0.28g, 0.001mol), potassium carbonate (3.34 g, 0.024mol) and the mixture toluene 25 mL, tetrahydrofuran, 25mL, 10 mL of water were placed. The temperature of the reactor temperature was raised to 80 degrees and stirred overnight.When the reaction is complete cool down the temperature of the reactor to room temperature and concentrated under reduced pressure and extracted with ethyl acetate. Separated by column chromatography and recrystallized with toluene and acetone to give the [formula 22] (3g). (37.3%). The [Reaction Scheme 14] In the Formula 2-b] Instead of using a 1,4-dibromo-naphthalene, and [Formula 2-a] except that instead of the phenyl boronic acid and anthracene is, using the same method [Chemical Formula 6 got the -h] (28.5 g). (Yield: 84.3%)
84.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 24h;Reflux; The procedure of Synthesis Example 1-4 was repeated except that <strong>[83-53-4]1,4-dibromonaphthalene</strong> was used instead of 1-bromo-4-iodobenzene to obtain 28.5 g of . (Yield: 84.3%)
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 2h; Preparation of Compound (262); In toluene (200 mL) and ethanol (100 mL), dissolved were Compound (261) (7.1 g, 23.8 mmol), <strong>[83-53-4]1,4-dibromonaphthalene</strong> (7.5 g, 26.2 mmol) and tetrakispalladium (O) triphenylphosphine (Pd(PPh3)4) (2.8 g, 2.4 mmol). To the solution, aqueous 2M sodium carbonate solution (120 mL) was added, and the mixture was stirred at 120 C. under reflux for 2 hours. Then, the mixture was cooled to 25 C., and the reaction was quenched by adding distilled water (200 mL). The reaction mixture was extracted with ethyl acetate (100 mL), and the extract was dried under reduced pressure. Recrystallization from tetrahydrofuran (10 mL) and methanol (200 mL) gave the objective compound (262) (6.6 g, 14.4 mmol).
  • 7
  • [ 334658-75-2 ]
  • [ 1335127-06-4 ]
  • [ 1335127-07-5 ]
YieldReaction ConditionsOperation in experiment
81% With sodium carbonate In ethanol; water; toluene at 100℃; 1 Preparation of Compound 1; [146] 10-phenylanthracene-9-ylboronic acid (32g, 107mmol), Compound 1-3 (25g, 82mmol), Pd(PPh3)4 (6.2g, 5.4mmol) and Na2CO3 (17.4g, 164mmol) were dissolved in toluene/ethanol/distilled water 400mL/100mL/80mL and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with distilled water and EA. After drying an organic layer with MgSO4 and removing solvent by a rotary type evaporator, Target Compound 1 (3g, 81%) was obtained by purification via column chromatography using dichloromethane and hexane as an eluent.
  • 8
  • [ 150-46-9 ]
  • [ 23674-20-6 ]
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.2% Exemplary Synthesis 2; Synthesis of Compound 2; Synthesis of 10-Phenylanthracene-9-Boronic Acid; An amount of 15.14 g (58.9 mmol) of 9-bromoanthracene, 7.2 g (59 mmol) of phenylboronic acid, and 1 g of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 100 ml of toluene and 25 ml of ethanol. Then, 50 ml of 2M sodium carbonate solution was added to the mixed solvent and allowed to react at 90 C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 13.65 g (53.7 mmol) of 9-phenylanthracene. The yield was 91.2%.An amount of 13.65 (53.7 mmol) of 9-phenylanthracene was dissolved in 100 ml of N,N dimethylformamide. An amount of 10.5 g (59 mmol) of N bromosuccinimide was added and allowed to react for six hours. Then, distilled water was added to stop the reaction and the deposit was filtered. The recovered deposit was purified by column chromatography to obtain 15.97 g (48 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong>. The yield was 89.3%.An amount of 14 g (42 mmol) of <strong>[23674-20-6]9-bromo-10-phenylanthracene</strong> was dissolved in dehydrated THF and cooled to -80 C. Then, 31.2 ml (49 mmol) of a solution of n-butyllithium in n-hexane was added dropwise. Forty minutes later, 13 g (89 mmol) of triethyl borate was added. After two-hour reaction, a diluted hydrochloric acid solution was added and allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 10 g (33.6 mmol) of 10-phenylanthracene-9-boronic acid. The yield was 75.2%.(Synthesis of Compound 2); An amount of 0.94 g (3.14 mmol) of 10-phenylanthracene-9-boronic acid, 1.52 g (3.14 mmol) of 9-bromo-7,12-diphenybenzofluoranthene synthesized in the same manner as in Exemplary Synthesis 1, and 100 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 80 ml of toluene and 20 ml of ethanol. Then, 40 ml of 2M sodium carbonate solution was added and allowed to react at 90 C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 1.37 g (2.09 mmol) of Compound 2. The yield was 66.6%.The obtained Compound 2 was identified by the mass spectrum, infrared absorption spectrum, and NMR.
  • 9
  • [ 334658-75-2 ]
  • [ 1198806-84-6 ]
  • [ 1350928-46-9 ]
YieldReaction ConditionsOperation in experiment
66.6% With sodium carbonate In ethanol; water; toluene at 90℃; for 12h; 2 Synthesis of 9-phenyl-10-(4-bromophenyl)anthracene Exemplary Synthesis 2; Synthesis of Compound 2; Synthesis of 10-Phenylanthracene-9-Boronic Acid; An amount of 15.14 g (58.9 mmol) of 9-bromoanthracene, 7.2 g (59 mmol) of phenylboronic acid, and 1 g of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 100 ml of toluene and 25 ml of ethanol. Then, 50 ml of 2M sodium carbonate solution was added to the mixed solvent and allowed to react at 90° C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 13.65 g (53.7 mmol) of 9-phenylanthracene. The yield was 91.2%.An amount of 13.65 (53.7 mmol) of 9-phenylanthracene was dissolved in 100 ml of N,N dimethylformamide. An amount of 10.5 g (59 mmol) of N bromosuccinimide was added and allowed to react for six hours. Then, distilled water was added to stop the reaction and the deposit was filtered. The recovered deposit was purified by column chromatography to obtain 15.97 g (48 mmol) of 9-bromo-10-phenylanthracene. The yield was 89.3%.An amount of 14 g (42 mmol) of 9-bromo-10-phenylanthracene was dissolved in dehydrated THF and cooled to -80° C. Then, 31.2 ml (49 mmol) of a solution of n-butyllithium in n-hexane was added dropwise. Forty minutes later, 13 g (89 mmol) of triethyl borate was added. After two-hour reaction, a diluted hydrochloric acid solution was added and allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 10 g (33.6 mmol) of 10-phenylanthracene-9-boronic acid. The yield was 75.2%.(Synthesis of Compound 2); An amount of 0.94 g (3.14 mmol) of 10-phenylanthracene-9-boronic acid, 1.52 g (3.14 mmol) of 9-bromo-7,12-diphenybenzofluoranthene synthesized in the same manner as in Exemplary Synthesis 1, and 100 mg of tetrakis triphenylphosphine palladium as catalysis were dissolved in a mixed solvent of 80 ml of toluene and 20 ml of ethanol. Then, 40 ml of 2M sodium carbonate solution was added and allowed to react at 90° C. for 12 hours. After the reaction was completed, the organic layer was separated and purified by column chromatography to obtain 1.37 g (2.09 mmol) of Compound 2. The yield was 66.6%.The obtained Compound 2 was identified by the mass spectrum, infrared absorption spectrum, and NMR.
  • 10
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 1257220-44-2 ]
  • [ 1604840-44-9 ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 100℃; for 12h;Inert atmosphere; <strong>[1257220-44-2]2-bromo-7,7-dimethyl-5-phenyl-5,7-dihydroindeno[2,1-b]carbazole</strong>(0.9 g, 2.0 mmol), 1.5 equivalent of arylboronic acid, 2M K2CO3(10 mL), and Pd(PPh3)4 (0.023 g, 0.02 mmol) were added to 1,4-dioxane(80 mL), and stirred at 100 C for 12 h under nitrogen atmosphere.The organic layer was concentrated and purified by silica gelcolumn chromatography using an eluent mixture of dichloromethaneand petroleum ether in the volume ratio of 1:3, which give a whitepowder with 0.96 g (yields: 77%) and 0.84 g (yields: 73%), respectively.IDC-PA: mp: 334 C (760 mmHg). IR (KBr): v 3062, 2955, 1595, 1505,1452, 1388, 1298, 1230, 763, 752 cm-1. 1H NMR (600 MHz, CDCl3) δ8.65 (s, 1H), 7.92 (d, J=8.4 Hz, 2H), 7.85 (d, J=8.4 Hz, 1H),7.77-7.69 (m, 8H), 7.62 (dd, J=15.6, 7.8 Hz, 4H), 7.59-7.55 (m, 3H),7.45 (d, J=8.4 Hz, 1H), 7.41 (d, J=7.2 Hz, 1H), 7.36-7.31 (m, 6H),7.26 (d, J=7.2 Hz, 1H), 1.77 (s, 6H). 13C NMR (CDCl3, 400 MHz) (δ,ppm): 154.10, 148.23, 142.22, 141.12, 139.69, 138.65, 137.64, 132.93,132.25, 131.60, 131.11, 130.37, 130.07, 128.89, 128.35, 128.19,128.04, 127.89, 127.49, 127.43, 127.30, 126.90, 126.64, 126.03,126.02, 125.58, 125.03, 124.75, 124.73, 122.20, 118.86, 118.32,109.91, 109.12, 48.07, 24.16. Anal. calcd for C47H33N (%): C, 92.27; H,5.44; N, 2.29. Found: C, 92.31; H, 5.17; N, 2.52. MS (EI) m/z: 611.46[M+].
  • 11
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 27973-29-1 ]
  • 1,6-bis(10-phenylanthracene-9-yl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.8% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 120℃; for 48h; 1 Synthesis of Exemplary Compound H4 1.49 g (5.0 mmol) of 10-phenylanthracene-9-boronic acid and 0.72 g (2.0 mmol) of 1,6-dibromopyrene and 231 mg of tetrakistriphenylphosphine palladium as a catalyst were dissolved in 40 ml of toluene, 10 ml In a mixed solvent. To this was added 10 ml of 2 M sodium carbonate aqueous solution and the mixture was reacted at 120 ° C. for 2 days. After completion of the reaction, the organic layer was separated and purified by column chromatography to obtain 1.18 g (4.19 mmol) of Exemplified Compound H4. The yield was 83.8%.
78% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 3h; Reflux; 2.1.1. General Procedure for the Suzuki Cross-Coupling Reaction General procedure: 1-naphthyl boronic acid (9.174 mmol), 9-phenylanthracen-10-yl boronic acid and the corresponding 1,6-dibromopyrene1.0 g (2.78 mmol), Pd(PPh34 128 mg (0.11 mmol),aqueous 2.0 M Na2CO3 14 ml (27.8 mmol), Ethanol(14 ml) and toluene (28 ml) were mixed in a flask.The mixture was refluxed for 3 h. After the reaction had finished, the reaction mixture was extracted with ethyl acetate and washed with water. The crude products were purified through column chromatography and recrystallization.
  • 12
  • [ 334658-75-2 ]
  • [ 1627917-16-1 ]
  • [ 1627916-48-6 ]
YieldReaction ConditionsOperation in experiment
4.04 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 8h; Reflux; Inert atmosphere; 1 [Synthesis of anthracene derivative (compound 1)] In an argon atmosphere, 2.96g of intermediate (A), 3.28g of 10-phenylanthracene-9-boronic acid, that hadbeen prepared by a known method, 0.231g of tetrakis(triphenylphosphine)palladium (0), 20 mL of 1,2-dimethoxyethane,20 mL of toluene and 20 mL of a 2M aqueous sodium carbonate solution were charged. The resultant was stirred underreflux for 8 hours. After cooling to room temperature, precipitated solids were separated by filtration. The obtained solidswere washed with water and methanol, and re-crystallized from toluene, whereby 4.04g of pale yellow solids of compound1 were obtained. As a result of mass spectrometry, it was found that the obtained solids were an intended product, andhad an m/e of 470 relative to a molecular weight of 470.17.
  • 13
  • [ 334658-75-2 ]
  • [ 90-11-9 ]
  • [ 63018-93-9 ]
YieldReaction ConditionsOperation in experiment
38% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 74℃; for 3h; Inert atmosphere; 19 Synthesis of Compound (RC-1A) 9PA10BA 2.00g (6.71mmol, 1.0eq), 1-bromonaphthalene 1.39g (6.71mmol, 1.0eq.), Potassium phosphate 3.22g (3.0eq.) And tetrakis (triphenylphosphine ) palladium (0) 0.18g (0.03eq.) were weighed into 100mL three-neck round bottom flask, was carried out under reduced pressure degassing / Ar replaced five times.After thoroughly vacuum degassing and nitrogen substitution, toluene 16mL, the ethanol 4mL and water 4mL added under a nitrogen atmosphere and reflux and stirring at 74 .After 3 hours, stopped heating, the reaction mixture was returned to room temperature.After extraction three times with toluene, the combined organic solvent layer, anhydrous sodium sulfate was added and left for a while.Filtration of the sodium sulphate, the solution was concentrated under reduced pressure.The resulting oil using toluene as eluent leads to a silica gel short column chromatography and recovered and concentrated under reduced pressure The fractions containing the desired product.Heptane resulting oil eluent - leads to silica gel column chromatography using toluene, was collected, concentrated under reduced pressure The fractions containing the desired product.The resulting clear oil toluene in a good solvent, methanol poor solvent, or recrystallized with heptane, to recover a white powder.The resulting powder ×102-4 Pa or less under a reduced pressure, subjected to sublimation purification at 310 ° C., compound as a yellow-green glassy solid (RC-1A) were obtained (yield: 0.97 g, Yield: 38.0%, purity: 99.9% or more (HPLC)).
  • 14
  • [ 121-43-7 ]
  • [ 23674-20-6 ]
  • [ 7732-18-5 ]
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.3% <1-c> was synthesized by the following Scheme 3. In a 5000 mL round bottom flask, 360.21 g (1.085 mol) of <1-b> obtained from Scheme 2 were dissolved in 2900 mL of tetrahydrofuran under a nitrogen atmosphere and cooled to minus 70 degrees. After cooling, 813.68 mL (1.302 mol) of n-butyllithium (1.6 M hexane solution) is slowly added dropwise. After completion of the dropwise addition, the mixture was stirred for 2 hours and then trimethylborate 181.44 mL (1.627 mol) was added dropwise and stirred at room temperature for 12 hours.After completion of the reaction, 900 mL of 2 N hydrochloric acid solution was added thereto, stirred for 30 minutes, and ethyl acetate and water were added for extraction. The organic layer is anhydrous and concentrated under reduced pressure. When the solid precipitates during concentration under reduced pressure, add hexane, stir for 30 minutes, and filter 305.0 g (yield 94.3%) of <1-c> were obtained.
76.7% <strong>[23674-20-6]9-phenyl-10-bromo-anthracene</strong> (13.4 g, 40 mmol) was dissolved in 110 mL THF. In the cooling state up to -78C was put in the n-BuLi (30 mL) slowly. At the end of the addition and then stirred for about 1 hour at -78C was put trimethyl borate (5.9 g, 56 mmol). After 1 hour stirring at -78C stirred at room temperature for about two hours and put in a 2 N HCl was adjusted to acidic. The solvent was then extracted with EA and obtained with hexane to give the 9-phenyl-10-anthracene boronic acid 9.2g (yield 76.7%).
76.7% 9-phenyl-10-bromoanthracene (13.4 g, 40 mmol) was dissolved in 110 mL of THF. The n-BuLi (30 mL) was added slowly while cooling to -78 C. After the addition, trimethylborate (5.9 g, 56 mmol) was added at -78 C for about 1 hour. After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for 2 hours and 2N HCl was added to adjust the acidity. EA followed by removal of the solvent to obtain 9.2 g of 9-phenyl-10-anthraceneboronic acid (yield 76.7%).
76.7% In a round-bottom flask, 9-phenyl-10-bromoanthracene (26.8 g, 80 mmol) prepared in Synthesis Example 1-1-b was dissolved in 220 mL of THF. N-butyllithium (60 mL) was slowly added while cooling to -78 C.After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (11.8 g, 112 mmol) was added.After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid aqueous solution was added to adjust the acidity.After extraction with EA, the solvent was removed and crystals were obtained with hexane to obtain 18.4 g of 9-phenyl-10-anthraceneboronic acid (yield 76.7%).
76.7% In a round-bottom flask, 9-phenyl-10-bromoanthracene (26.8 g, 80 mmol) prepared in Synthesis Example 1-1-b was dissolved in 220 mL of THF. N-butyllithium (60 mL) was slowly added while cooling to -78 C. After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (11.8 g, 112 mmol) was added. After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid aqueous solution was added to adjust the acidity. After extraction with EA, the solvent was removed and crystals were obtained with hexane to obtain 18.4 g of 9-phenyl-10-anthraceneboronic acid (yield 76.7%).
76.7% In a round-bottom flask, 9-phenyl-10-bromoanthracene (26.8 g, 80 mmol) prepared in Synthesis Example 1-1-b was dissolved in 220 mL of THF. N-butyllithium (60 mL) was slowly added while cooling to -78 C.After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (11.8 g, 112 mmol) was added.After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid aqueous solution was added to adjust the acidity.After extraction with EA and removal of the solvent, crystals were obtained with hexane to obtain 18.4 g of 9-phenyl-10-anthraceneboronic acid (yield 76.7%).
76.7% 9-phenyl-10-bromoanthracene(13.4 g, 40 mmol) was dissolved in 110 mL of THF. Cooled to -78 n-BuLi (30 mL) was added slowly. After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (5.9 g, 56 mmol) was added.After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2 N HCl was added to adjust the acidity.After extraction with EA, the solvent was removed and crystals were obtained with hexane to obtain 9-phenyl-10-anthraceneboronic acid.9.2g (yield 76.7%) was obtained.

  • 15
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 1256544-20-3 ]
  • C36H22O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; 3-4 Synthesis Example 3-(4): Synthesis of Compound207 In a 250-mE round-bottom flask reactor, (10.0 g, 33.7 mmol), 10-phenyl-anthracene-9- boronic acid (11.0 g, 37 mmol), tetrakis(triphenylphosphine) palladium (0.8 g, 0.7 mmol), and potassium carbonate (9.3 g, 68 mmol) were placed, followed by toluene (50 mE), ethanol (50 mE) and water (30 mE). The mixture was heated to 90° C. and stirred overnight. Afier completion of the reaction, the reaction mixture was cooled to room temperatare, and stirred together with methanol (50 ml). The precipitate thus formed was filtered and washed with methanol. Recrystallization in toluene and acetone afforded as a solid. MS (MALDI-TOF): m/z 470.17 [M]
  • 16
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 108-36-1 ]
  • [ 1023674-80-7 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 8h; Inert atmosphere; Reflux; 1.1 (1) Synthesis of Intermediate A Under an argon atmosphere,200 g of 1,3-dibromobenzene,120 g of 10-phenyl-9-anthracene boronic acid,5 g of tetrakis triphenylphosphine dipalladium (0)1000 mL of toluene,A sodium carbonate aqueous solution (2 M, 500 mL) was charged in a flask,And heated under reflux for 8 hours. After heating under reflux, it was cooled to room temperature,The reaction solution was extracted with toluene. After drying the obtained organic layer,And concentrated.The obtained residue was purified by column chromatography to obtain 139 g of Intermediate A. The yield of Intermediate A was 85%.
70.3% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 5h; A 4.472 g (15.0mmol) 10-phenylanthracen-9-boron acid and 18.873 g (75.0mmol) of 1,3-dibromobenzene, 867 mg of tetrakistriphenyl phosphinepalladium as a catalyst was dissolved in 150 ml of toluene, and the mixed solvent of 50 ml of ethanol. 75 ml of sodium carbonate aqueous solutions of 2M were added here, and it reacted at 100 degrees C for 5 hours. The organic layer was separated after ending reaction, refining by column chromatography was performed, and 4.317 g (10.5mmol) of 9-(3-bromophenyl)-10-phenylanthracene was obtained. Yield was 70.3%.
65% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 16h; Inert atmosphere; 3 Synthesis of Compound (1-12) Under an argon stream, 3.26 g (10.9 mmol) of the compound (1-10) synthesized by the above reaction, 6.6 ml (54.8 mmol) of 1,3-dibromobenzene and 0.25 g (0.22 mmol) of tetrakis (triphenylphosphine) palladium (0) were dissolved in 60 ml of toluene and 8 ml of ethanol. Next, 17 ml of an aqueous solution containing 34.0 mmol of sodium carbonate was added and the mixture was stirred under reflux for 16 hours. After cooling to room temperature water was added to the reaction solution and extracted with toluene. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by column chromatography and a white solid (yield 2.92 g, yield 65%) of the desired compound (1-12) was obtained.
  • 17
  • [ 334658-75-2 ]
  • [ 589-87-7 ]
  • [ 625854-02-6 ]
YieldReaction ConditionsOperation in experiment
88.1% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate; toluene for 12h; Reflux; 2-1 Intermediate 2-a was synthesized according to Reaction Scheme 5 below. A 300 mL reactor was charged with 2,5-dibromobenzaldehyde (15.3 g, 58 mmol)9,9-dimethyl-9H-fluoren-2-ylboronic acid (14.7 g, 62 mmol)Potassium carbonate (16 g, 116 mmol),Tetrakis triphenylphosphine palladium (2.2 g, 1 mmol), H2O 30 mL,Add 75 mL of toluene and 75 mL of 1,4-dioxane, and stir at reflux for 12 hours. After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure, and the resultant product was separated by column chromatography to obtain (11 g, 50%). (Intermediate 2-a) (27.2 g, 88.1%) was obtained in the same manner as in Synthesis Example 1-4, except that 1-bromo-4-iodobenzene was used instead of Intermediate 1-c.
84.2% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate; toluene Reflux; 7.7-a Synthesis Example 7-a) Synthesis of 9-(4-bromophenyl)-10-phenylanthracene 9-phenyl-10-anthraceneboronic acid 9.2g (31mmol), 4-bromo-1-iodobenzene in a round bottom flask8.7 g (31 mmol), potassium carbonate 8.5 g (62 mmol),40.7 g (1 mmol) of Pd (PPh3), 20 ml of water, 50 ml of toluene and 50 ml of tetrahydrofuran were added and reacted at reflux.After the reaction was completed, the aqueous layer was removed by separating the layers, and the organic layer was concentrated under reduced pressure, using column chromatography.9- (4-bromophenyl) -10-phenylanthracene10.6 g(Yield 84.2%).
77% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In lithium hydroxide monohydrate; toluene for 24h; Reflux; 1.1-4 Synthesis of <1-d> 2 L reactor was charged with 90 g (446 mmol) of 1-bromo-4-iodobenzene, 92 g (535 mmol) of phenylanthraceneboronic acid,123.2 g (891 mmol) of potassium carbonate, 17.2 g (9 mmol) of tetrakis (triphenylphosphine) palladium, 180 mL of H 2 O and 720 mL of toluene were added and the mixture was stirred under reflux for 24 hours.The reaction mixture is separated at room temperature and the organic layer is concentrated under reduced pressure. Separation by column chromatography gave 103 g (yield 77%).
73% With tris-(dibenzylideneacetone)dipalladium(0); tetraethylammonium hydroxide; tris-(o-tolyl)phosphine In lithium hydroxide monohydrate; toluene at 115℃; for 18h; Inert atmosphere; In an embodiment, the preparation method comprises: placing (10-phenylanthracen-9-yl)boronic acid (2.98 g, 10 mmol), 1-bromo-4-iodobenzene (8.49 g, mmol), tris(dibenzylideneacetone)dipalladium(0) (0.915 g, 0.1 mmol), tri(o-tolyl)phosphine (0.913 g, 0.15 mmol) in a 250 ml two-neck bottle with a stir bar, and mixing with deoxidized toluene (45 ml) and a 20% tetramethylammonium hydroxide aqueous solution (45 ml) after carrying out argon replacement thrice; heating the mixture to 115° C., and refluxing for 18 hours; after the reaction, subjecting the mixture to vortex concentration to remove toluene, and carrying out extraction twice with dichloromethane; washing the organic layer with a saturated salt solution once, dehydrating with anhydrous magnesium sulfate, and subjecting to silica gel column chromatography (eluent: Hex: DCM=10: 1); after concentration, recrystallizing the solid with normal hexane and dichloromethane to obtain 3.01 g of a white solid, whose yield reaches 73%. The structural identification data is as follows: 1H NMR (400 MHz, d-DMSO) δ 7.86(d, J=8.4 Hz), 7.69-7.56(m, 7H), 7.47-7.43(m, 8H) ; 13C NMR (100 MHz, CDCl3) δ 166.12, 163.31, 142.12, 138.13, 134.84, 132.92, 131.28, 130.89, 129.84, 129.21, 128.90, 128.52, 128.09, 128.01, 127.97, 127.66, 127.53, 127.38, 127.16, 125.60, 125.11, 123.33, 121.19, 117.49 HRMS (MALDI) m/z calcd for C26H17Br 408.0514. obsd. 408.0522.
70% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene at 80℃; Inert atmosphere;
66% With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In ethanol; toluene at 80℃; for 12h; Inert atmosphere;
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene

  • 18
  • [ 334658-75-2 ]
  • [ 2229954-60-1 ]
  • [ 2229954-30-5 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In ethanol; toluene at 90℃; for 12h; 3.1 (1) Synthesis of Compound 1-3 (6-(10-phenylanthracen-9-yl)-2-(4-(pyrimidin-2-yl)phenyl)-1,10-phenanthroline) Intermediate C (8 g, 19.4 mmol) and (10-phenylanthracen-9-yl)boronic acid (6.9 g, 23.2 mmol) were dissolved in toluene and the mixture was stirred with ethanol and 4M K2CO3 for 12 hours at 90 °C and the mixture was refluxed and stirred. After completion of the reaction, the reaction product was precipitated with distilled water and methanol. Dried, and subjected to column purification (MC), and recrystallized with Hx to obtain 9.6 g (yield: 85%).
85% With potassium carbonate In ethanol; toluene at 90℃; for 12h; 3.1 (1) Synthesis of Compound(1-3) Synthesis of 6-(10-phenylanthracen-9-yl)-2-(4-(pyrimidin-2-yl)phenyl)-1,10-phenanthroline To a round bottom flask was added intermediate C (8 g, 19.4 mmol), (10-phenylanthracen-9-yl)boronic acid (6.9 g, 23.2 mmol) dissolved in toluene, and then refluxed with ethanol and 4M K2CO3 at 90 ° C for 12 hours.After completion of the reaction, the reaction product was precipitated with distilled water and methanol. Dried and then subjected to column purification (MC) and recrystallized with Hx to obtain 9.6 g (yield: 85%).
  • 19
  • [ 334658-75-2 ]
  • [ 2252254-00-3 ]
  • [ 2252254-01-4 ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 100℃; for 24h; Inert atmosphere;
  • 20
  • [ 334658-75-2 ]
  • [ 872118-06-4 ]
  • [ 2674202-91-4 ]
YieldReaction ConditionsOperation in experiment
30% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 95℃; for 48h; Inert atmosphere; A flask was flushed with nitrogen and charged with 3-bromo-3',4',5'-triphenyl- l,l':2',l"-terphenyl (15.0 g, 1.2 eq., 27.9 mmol), (l0-phenylanthracen-9-yl)boronic acid (6.0 g, 1.0 eq., 23.2 mmol), tetrakis(triphenylphosphine)palladium(0) (0.54 g, 0.02 eq., 0.47 mmol) and potassium carbonate (9.6 g, 3.0 eq., 69.8 mmol). A deaerated mixture of toluene (300 mL), ethanol (60 mL) and water (30 mL) was added and the reaction mixture was heated up to 95 °C and left to react under nitrogen atmosphere. After 2 days of reflux, the reaction mixture was cooled down to room temperature. The organic layer was then decanted, washed with water (3 x 150 mL), and dried over Na2S04. The drying agent was filtered off. The resulting solution was filtered over silica using toluene (300 mL) as eluent. The filtrate was reduced under vacuum till ca. 60 mL, and hexane (100 mL) was added dropwise. The suspension was stirred overnight. The precipitate was filtered, rinsed first with toluene / hexane 1 / 2 (10 mL), then with hexane (10 mL). Crude solid was redissolved in dichloromethane (100 mL) and hexane was added (150 mL). Precipitate was filtered and washed with dichloromethane / hexane 1 / 1.5 (2 x 50 mL). Solid was dissolved in glyme (60 mL), the suspension was cooled down slightly, and precipitation was favored upon addition of hexane (50 mL). The suspension was then cooled down to room temperature and the solid was filtered, washed with hexanes and dried overnight at 80°C under vacuum to afford the title compound in 30 % yield (4.9 g), as a white solid. ESI-MS: 711 (M+H).
  • 21
  • [ 334658-75-2 ]
  • [ 2097124-40-6 ]
  • [ 2412108-85-9 ]
YieldReaction ConditionsOperation in experiment
92% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10h; Heating; 6 Synthesis of Step 1-6 and Step 2-6 General procedure: B1-1 to B1-14, C3-1 to C3-4, B1-2, A1-1 and B1-4(1eq) and SM2 (1.03eq) shown in Table 6 below are tetrahydrofuranAfter adding to (excess), 2M potassium carbonate aqueous solution (30 volume ratio compared to THF) was added, and tetrakistriphenyl-phosphino palladium(2 mol%) was added, followed by heating and stirring for 10 hours.After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed to separate the layers.After removal of the solvent, recrystallization with tetrahydrofuran and ethyl acetate to prepare compounds 1 to 20 of Table 6 below. In the above preparation examples, R101 to R104, R 'and R "each represent a substituent,L1 and L2 each represent a linking group, a, b, c and d each indicate the number of substituents, X represents a sulfonyl group.
  • 22
  • [ 334658-75-2 ]
  • [ 2142681-84-1 ]
  • [ 2438168-58-0 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 10-phenylanthracene-9-boronic acid; 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine With potassium carbonate In tetrahydrofuran; water for 1h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; water at 75℃; for 19h; Inert atmosphere; Synthesis of 2-(dibemo[b,d]furan-3-yl)-4-phenyI-6-(io-phenylanthracen- 9-yl)-i,3,5-triazme CET-4) In a goomt 3-necked flask, were placed following compounds: 2-chloro-4~ (dibenzo[b,d]furan-3-yl)-6-phenyl-i,3,5-triazine (A, log, 28mmol, leq.) , phenylanthranylboronic acid (B, 9.2g, 3immo, l.ieq.) and potassium carbonate (y.yg, Sg.gmmol, 2eq.) together with THF (224mL) and dest. water >6mL). The yellow suspension was degassed by bubbling N2 for 60 minutes. Then Pd(dppf)Cl2 (o.ig, o.i4mmol, o.5%molar) was added under nitrogen counter flow. The reaction was then heated lgh at 75°C (bath temperature) under nitrogen. TLC control shows reaction completion. After cooling to rt and evaporation of the solvent, residue was extracted with.4L DCM/Chloroform and the organic layer washed in portions with in total 7.5L of water until pH neutral. After filtering over Florisil layer, the organic layer was evaporated and the residue treated by aoomL hexane. Precipitate was filtered and dried under high vacuum two times at 120°C (melting). Obtained i44g (89%). MS [M+H]+ 576.
  • 23
  • 10-phenylanthracene-9-boronic acid [ No CAS ]
  • [ 715-50-4 ]
  • 9-phenanthren-3-yl-10-phenylanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water; toluene at 80℃; for 24h; 1.1-1 [0185] 20 g (0.08 mol) of 3-bromophenanthrene, 30.15 g (0.1 mol) of phenylanthracene boronic acid, 21.5 g (0.16 mol) of potassium carbonate (K2CO3), 1.8 g (0.002 mol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), 100 mL of toluene, 100 mL of 1,4-dioxane, and 40 mL of water were placed in a 1 L round-bottom flask. The mixture was refluxed with stirring at 80°C. for 24 h. After completion of the reaction, the resulting mixture was allowed to stand at room temperature for layer separation. The aqueous layer was removed, and the organic layer was concentrated under reduced pressure and purified by column chromatography to give Compound A1 (15.7 g, 64%). [0186] MS (MALDI-TOF): m/z 430.17 [M*]
  • 24
  • [ 334658-75-2 ]
  • [ 102587-98-4 ]
  • [ 1620892-64-9 ]
YieldReaction ConditionsOperation in experiment
80% With tetrabutylammomium bromide; potassium carbonate In water; toluene at 110℃; for 2h; 1 Synthesis of Compound 1 Add 5g (0.017mol) of (10-phenylanthracene-9-yl)boronic acid, 3g (0.0085mol)2,7-dibromopyrene, 2.3g (0.017mol) K2CO3 and 2.7g (0.0085mol)Tetrabutylammonium bromide dissolved in 200ml of water and toluene (1:1) as a solvent,And it was stirred at a temperature of 110°C for 2 hours under reflux. The reaction mixture was extracted with dichloromethane and distilled water. The organic layer was washed three times with distilled water and dried with magnesium sulfate,It was filtered, and then concentrated under reduced pressure.The concentrate was purified by column chromatography to obtain 2.4 g (80% yield) of Compound 1.
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