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[ CAS No. 597554-03-5 ] {[proInfo.proName]}

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Chemical Structure| 597554-03-5
Chemical Structure| 597554-03-5
Structure of 597554-03-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 597554-03-5 ]

CAS No. :597554-03-5 MDL No. :MFCD11973625
Formula : C24H17BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YGVDBZMVEURVOW-UHFFFAOYSA-N
M.W : 348.20 Pubchem ID :23088556
Synonyms :

Calculated chemistry of [ 597554-03-5 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 114.22
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 6.2
Log Po/w (WLOGP) : 4.49
Log Po/w (MLOGP) : 4.17
Log Po/w (SILICOS-IT) : 3.97
Consensus Log Po/w : 3.77

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.43
Solubility : 0.000129 mg/ml ; 0.000000371 mol/l
Class : Poorly soluble
Log S (Ali) : -6.83
Solubility : 0.000051 mg/ml ; 0.000000146 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.79
Solubility : 0.000000561 mg/ml ; 0.0000000016 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.58

Safety of [ 597554-03-5 ]

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

Application In Synthesis of [ 597554-03-5 ]

* 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 [ 597554-03-5 ]

[ 597554-03-5 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 597554-03-5 ]
  • [ 128143-89-5 ]
  • 4'-(10-naphthalen-2-yl-anthracene-9-yl)-[2,2',6',2'']terpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 7h;Heating / reflux; Two grams (5.7 mmol) of 4'-chloro- [2,2';6',2''] terpyridine, 2.0 g (5.7 mmol) of 10-naphthalen-2-yl-anthrathene-9-boronic acid and 0.14 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, and adding 9 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 7 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the resultant substance was washed with methanol thereby obtaining 2.33 g of yellowish white solid (yield: 84 %). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance (Compound 5-4), and it was recognized that m/e= 535 for molecular weight of 535.20.
  • 2
  • [ 597554-03-5 ]
  • [ 34658-66-7 ]
  • 2-[4-(10-naphthalen-2-yl-anthracen-9-yl)-phenyl]-imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux; One point five grams (5.5 mmol) of 2-(4-bromo-phenyl)-imidazo [1,2-a] pyridine obtained in the above step (1), 2.0 g (5.78 mmol) of 10-naphthalen-2-yl-anthrathene-9-boronic acid and 0.13 g of tetrakis (triphenylphosphine) palladium into 30 milliliter of 1,2-dimethoxyethane, and adding 8.6 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the resultant substance was washed with methanol thereby obtaining 1.2 g of yellowish white solid (yield: 45 %). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance (Compound 14-7), and it was recognized that m/e= 496 for molecular weight of 496.19.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 3h;Inert atmosphere; Synthesis (D1-4); Under an Ar atmosphere, in a 500 ml flask, 2 g of boronic acid product obtained from synthesis (D1-2) and 1.7 g of imidazopyridine derivative obtained from synthesis (D1-3) were dissolved in 200 ml of dimethoxyethane and were heated to 80 C. 250 ml of distilled water and 10 g of sodium carbonate were added thereto. Also, 0.5 g of tetrakis-triphenylphosphine palladium(0) was added thereto.After 3 hours, extraction with toluene was carried out in a separatory funnel and purification using silica gel (SiO2, 500 g) was carried out.As a result, 2 g of white solid (a compound expressed by the Formula ETL-A3) was obtained.
2 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; at 80℃; for 3h;Inert atmosphere; Under Ar, 500 ml flask, 2 g (D1 d 2) obtained in the synthesis of the boronic acid, 1.7 g of the obtained composite (D1 d 3) was dissolved in 200 ml of dimethoxyethane imidazopyridine derivative, was heated to 80 C. 250 ml distilled water and sodium carbonate 10 g was placed therein. Further thereto was placed 0.5 g (0) tetrakistriphenylphosphine. 3 hours after the separatory funnel by extraction with toluene, silica (SiO2 500 g) was purified. Therefore, white solid (compound represented by the formula ETL a-A3) 2 g was obtained.
  • 3
  • [ 597554-03-5 ]
  • [ 1207-69-8 ]
  • 9-(10-naphthalen-2-yl-anthracen-9-yl)-acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux; One point three grams (6.1 mmol) of 9-chloro-acridine, 2.0 g (5.7 mmol) of 10-naphthalen-2-yl-anthrathene-9-boronic acid and 0.10 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, and adding 8 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the resultant substance was washed with methanol thereby obtaining 2.16 g of yellowish white solid (yield: 74 %). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance (Compound 13-4), and it was recognized that m/e= 481 for molecular weight of 481.18.
  • 4
  • [ 597554-03-5 ]
  • [ 58536-46-2 ]
  • 4-[4-(10-naphthalen-2-yl-anthracen-9-yl)-phenyl]-2,6-diphenyl-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux; One point eight grams (4.6 mmol) of 4-(4-bromo-phenyl)-2,6-diphenyl-pyrimidine obtained in the above step (2), 1.6 g (4.6 mmol) of 10-naphthalen-2-yl-anthrathene-9-boronic acid and 0.11 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, and adding 7 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the resultant substance was washed with methanol thereby obtaining 2.1 g of yellowish white solid (yield: 74 %). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance (Compound 2-4), and it was recognized that m/e= 610 for molecular weight of 610.24.
  • 5
  • [ 597554-03-5 ]
  • [ 73402-91-2 ]
  • 2-[4-(10-naphthalen-2-yl-anthracen-9-yl)-phenyl]-4-phenyl-quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux; Two grams (5.6 mmol) of 2-(4-bromo-phenyl)-4-phenyl-quinoline obtained in the above step (1), 2.0 g (5.7 mmol) of 10-naphthalen-2-yl-anthrathene-9-boronic acid and 0.10 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, and adding 8 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the resultant substance was washed with methanol thereby obtaining 2.07 g of yellowish white solid (yield: 64 %). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance (Compound 10-18), and it was recognized that m/e =583 for molecular weight of 583.23.
  • 6
  • [ 597554-03-5 ]
  • [ 94255-63-7 ]
  • 9-[4-(10-naphthalen-2-yl-anthracene-9-yl)-phenyl]-acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux; One point six grams (4.8 mmol) of 4-(4-bromo-phenyl)-acridine, 1.6 g (4.6 mmol) of 10-naphthalen-2-yl-anthrathene-9-boronic acid and 0.11 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, and adding 7 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the resultant substance was washed with methanol thereby obtaining 1.98 g of yellowish white solid (yield: 74 %). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance (Compound 13-11), and it was recognized that m/e= 557 for molecular weight of 557.21.
  • 7
  • [ 597554-03-5 ]
  • [ 64493-70-5 ]
  • 6-[4-(10-naphthalen-2-yl-anthracen-9-yl)-phenyl]-3-phenyl-[1,2,4]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 6h;Heating / reflux; One point six grams (5.1 mmol) of 6-(4-bromo-phenyl)-3-phenyl-[1,2,4] triadine obtained in the above step (1), 1.8 g (5.2 mmol) of 10-naphthalen-2-yl-anthrathene-9-boronic acid and 0.10 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, and adding 10 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the resultant substance was washed with methanol thereby obtaining 1.17 g of yellowish white solid (yield: 43 %). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance (Compound 6-18), and it was recognized that m/e= 535 for molecular weight of 535.20.
  • 8
  • [ 597554-03-5 ]
  • [ 4044-98-8 ]
  • 6-(10-naphthalen-2-yl-anthracen-9-yl)-2-phenyl-imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 7h;Heating / reflux; Dissolving 2.0 g (7.3 mmol) of 6-bromo-2-phenyl-imidazo [1,2-a] pyridine, 2.5 g (11 mmol) of 10-naphthalen-2-yl-anthracene-9-boronic acid and 0.17 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, adding 11 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystal were washed with water and methanol, thereby obtaining 2.7 g of yellowish white solids (yield: 75 %). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance, and it was recognized that m/e= 496 for molecular weight of 496.19.
  • 9
  • [ 597554-03-5 ]
  • [ 726138-24-5 ]
  • 2-[4-(10-naphthalen-2-yl-anthracen-9-yl)-phenyl]-6-phenyl-imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 7h;Heating / reflux; Dissolving 4.0 g (11 mmol) of 2-(4-bromo-phenyl)-6-phenyl-imidazo [1,2-a] pyridine, 4.0 g (11 mmol) of 10-naphthalen-2-yl-anthracene-9-boronic acid and 0.27 g of tetrakis (triphenylphosphine) palladium into 40 milliliter of 1,2-dimethoxyethane, adding 18 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and methanol, thereby obtaining 4.9 g of yellowish white solids (yield: 76 %). As a result of mass spectrum (MS) analysis, it was recognized that m/e= 572 for molecular weight of 572.23 and the yellowish white solids were identified as the aimed substance.
  • 10
  • [ 597554-03-5 ]
  • [ 726138-32-5 ]
  • 2-[4-(10-naphthalen-2-yl-anthracen-9-yl)-phenyl]-6-phenyl-imidazo[1,2-a]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 7h;Heating / reflux; Dissolving 3.0 g (8.6 mmol) of 2-(4-bromo-phenyl)-6-phenyl-imidazo [1,2-a] pyridine, 3.0 g (8.6 mmol) of 10-naphthalen-2-yl-anthracene-9-boronic acid and 0.20 g of tetrakis (triphenylphosphine) palladium into 30 milliliter of 1,2-dimethoxyethane, adding 13 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water, methanol and toluene, thereby obtaining 3.0 9 g of yellowish white solids (yield: 62 %). As a result of mass spectrum (MS) analysis, it was recognized that m/e= 573 for molecular weight of 573.22 and the yellowish white solids were identified as the aimed substance.
  • 11
  • [ 597554-03-5 ]
  • [ 2620-76-0 ]
  • 2-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-1-phenyl-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 7h;Heating / reflux; (2) Synthesis of 2-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-1-phenyl-1H-benzimidazole (Compound (1-7)) Dissolving 4.0 g (11 mmol) of 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole, 4.0 g (11 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.27 g of tetrakis (triphenylphosphine) palladium into 40 milliliter of 1,2-dimethoxyethane, adding 18 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and methanol, thereby obtaining 5.1 g of yellowish white solids (yield: 78 %). As a result of mass spectrum (MS) analysis, it was recognized that the yellowish white solids were identified as the aimed substance and that m/e= 572 for molecular weight of 572.23.
  • 12
  • [ 597554-03-5 ]
  • [ 760212-50-8 ]
  • 2-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-1-(pyridin-2-yl)-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; (4) Synthesis of 2-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-1-(2-pyridyl)-1H-benzimidazole (Compound (3-1)) Dissolving 3.5 g (10 mmol) of 1-(2-pyrizyl)-2-(4-bromophenyl)-1H-benzimidazole obtained in the above step (3), 4.2 g (12.1 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.23 g (0.20 mmol) of tetrakis (triphenylphosphine) palladium into 60 milliliter of 1,2-dimethoxyethane, adding 30 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 8 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water, methanol and toluene, thereby obtaining 5.0 g of greenish white solids (yield: 86 %). As a result of MS analysis, it was recognized that the greenish white solids were identified as the aimed substance and that m/e= 573 for molecular weight of 573.22.
  • 13
  • [ 597554-03-5 ]
  • [ 760212-55-3 ]
  • [ 760212-56-4 ]
YieldReaction ConditionsOperation in experiment
49% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; (4) Synthesis of 1,2-diphenyl-5-(10-naphthalene-2-yl-anthracene-9-yl)-1H-benzimidazole (Compound (7-2)) Dissolving 2.5 g (7.1 mmol) of 5-bromo-1,2-diphenyl-1H-benzimidazole obtained in the above step (3), 3.0 g (8.5 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.16 g (0.14 mmol) of tetrakis (triphenylphosphine) palladium into 60 milliliter of 1,2-dimethoxyethane, adding 30 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 8 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water, methanol and toluene, thereby obtaining 2.0 g of greenish white solids (yield: 49 %). As a result of MS analysis, it was recognized that the yellowish white solids were identified as the aimed substance and that m/e= 572 for molecular weight of 572.23.
  • 14
  • [ 597554-03-5 ]
  • [ 760212-58-6 ]
  • 1-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-2-phenyl-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; toluene; for 7h;Heating / reflux; (4) Synthesis of 1-[4-(10-naphthalene-2-yl-anthracene-9-yl) phenyl]-2-phenyl-1H-benzimidazole (Compound (9-7)) Dissolving 1.0 g (2.9 mmol) of <strong>[760212-58-6]1-(4-bromophenyl)-2-phenyl-1H-benzimidazole</strong> obtained in the above step (3), 1.1 g (3.1 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.1 g (0.09 mmol) of tetrakis (triphenylphosphine) palladium into 15 milliliter of 1,2-dimethoxyethane and 2 milliliter of toluene, adding 5 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and methanol, thereby obtaining 1.45 g of cream color solids (yield: 89 %). As a result of MS analysis, it was recognized that the cream color solids were identified as the aimed substance and that m/e= 572 for molecular weight of 572.23.
  • 15
  • [ 597554-03-5 ]
  • [ 107411-29-0 ]
  • 1-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-2-methyl-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 7h;Heating / reflux; (3) Synthesis of 1-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-2-methyl-1H-benzimidazole (Compound (12-2)) Dissolving 3.3 g (11 mmol) of 1-(4-bromophenyl)-2-methyl-1H-benzimidazole, 4.0 g (11 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.27 g of tetrakis (triphenylphosphine) palladium into 40 milliliter of 1,2-dimethoxyethane, adding 20 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 7 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with sodium sulfate. Removing the solvent by distillation and by refining the resultant product with the use of a silicagel column chromatography (dichloro methane - ethyl acetate), 2.9 g of yellowish white solids were obtained (yield: 49 %). As a result of MS analysis, it was recognized that the yellowish white solids were identified as the aimed substance and that m/e= 510 for molecular weight of 510.21.
  • 16
  • [ 597554-03-5 ]
  • [ 760212-69-9 ]
  • [ 760212-70-2 ]
YieldReaction ConditionsOperation in experiment
37% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; (3) Synthesis of 2-methyl-5-(10-naphthalene-2-yl-anthracene-9-yl)-1-phenyl-1H-benzimidazole (Compound (14-7)) Dissolving 3.0 g (11 mmol) of 5-bromo-2-methyl-1-phenyl-1H-benzimidazole obtained in the above step (2), 4.5 g (13 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.25 g (0.22 mmol) of tetrakis (triphenylphosphine) palladium into 60 milliliter of 1,2-dimethoxyethane, adding 30 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating under an atmospnere of argon gas for 8 hours. After completion of the reaction, separation with filtration was carried out and resultant solids were washed with water, methanol and toluene, thereby obtaining greenish white solids. Re-crystallizing the greenish white solids with the use of toluene, 2.0 g of yellowish green solids were obtained (yield: 37 %). As a result of MS analysis, it was recognized that the yellowish green solids were identified as the aimed substance and that m/e= 510 for molecular weight of 510.21.
  • 17
  • [ 597554-03-5 ]
  • [ 760212-73-5 ]
  • [ 760212-74-6 ]
YieldReaction ConditionsOperation in experiment
74% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; (5) Synthesis of 1-methyl-5-(10-naphthalene-2-yl-anthracene-9-yl)-2-phenyl-1H-benzimidazole (Compound (15-8)) Dissolving 1.5 g (5.6 mmol) of 5-bromo-1-methyl-2-phenyl-1H-benzimidazole obtained in the above step (4), 2.3 g (5.6 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.12 g (0.11 mmol) of tetrakis (triphenylphosphine) palladium into 60 milliliter of 1,2-dimethoxyethane, adding 30 milliliter of 2.0M sodium carbonate aqueous solution, the resultant solution was refluxed with heating under an atmospnere of argon gas for 8 hours. After completion of the reaction, separation with filtration was carried out and resultant solids were washed with water, methanol and toluene, thereby obtaining greenish white solids. Re-crystallizing the greenish white solids with the use of toluene, 2.0 g of yellowish green solids were obtained (yield: 74 %). As a result of mass spectrum (MS) analysis, it was recognized that the yellowish green solids were identified as the aimed substance and that m/e= 510 for molecular weight of 510.21.
  • 18
  • [ 597554-03-5 ]
  • [ 760212-76-8 ]
  • [ 760212-77-9 ]
YieldReaction ConditionsOperation in experiment
61% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; (3) Synthesis of 5-(10-naphthalene-2-yl-anthracene-9-yl)-1-phenyl-2-(2-pyridyl)-1H-benzimidazole Dissolving 2.0 g (5.8 mmol) of 5-bromo-1-phenyl-2-(2-pyridyl)-1H-benzimidazole obtained in the above step (2), 2.2 g (6.3 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.13 g (0.11 mmol) of tetrakis (triphenylphosphine) palladium into 30 milliliter of 1,2-dimethoxyethane, adding 15 milliliter of 2.0M sodium carbonate aqueous solution, the resultant solution was refluxed with heating under an atmosphere of argon gas for 8 hours. After completion of the reaction, separation with filtration was carried out and resultant solids were washed with water, methanol and toluene, thereby obtaining 2.0 g of greenish white solids (yield: 61 %). As a result of mass spectrum (MS) analysis, it was recognized that the greenish white solids were identified as the aimed substance and that m/e= 573 for molecular weight of 573.22.
  • 19
  • [ 597554-03-5 ]
  • [ 760212-61-1 ]
  • 2-[6-(10-naphthalene-2-yl-anthracene-9-yl)-pyridyl-2-yl]-1-phenyl-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; (3) Synthesis of 2-[6-(10-naphthalene-2-yl-anthracene-9-yl)-pyridyl-2-yl]-1-phenyl-1H-benzimidazole (Compound (4-5)) Dissolving 3.0 g (8.6 mmol) of 2-(6-bromopyridyl-2-yl)-1-phenyl-1H-benzimidazole obtained in the above step (2), 3.6 g (10 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.20 g (0.17 mmol) of tetrakis (triphenylphosphine) palladium into 60 milliliter of 1,2-dimethoxyethane, adding 30 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 8 hours. After completion of the reaction, separation with filtration was carried out and resultant solids were washed with water, methanol and toluene, thereby obtaining 2.0 g of greenish white solids (yield: 41 %). As a result of MS analysis, it was recognized that the greenish white solids were identified as the aimed substance and that m/e= 573 for molecular weight of 573.22.
  • 20
  • [ 597554-03-5 ]
  • [ 760212-64-4 ]
  • C42H27N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 7h;Heating / reflux; (3) Synthesis of 1-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-2-methyl-1H-benzimidazole (Compound (11-1)) Dissolving 1.2 g (3.4 mmol) of 1-(4-bromophenyl)-2-pyridine-2-yl-1H-benzimidazole, 1.2 g (3.4 mmol) of 10-naphthalene-2-yl-anthracene-9-boronic acid and 0.10 g of tetrakis (triphenylphosphine) palladium into 15 milliliter of 1,2-dimethoxyethane, adding 6 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed with heating for 7 hours. After completion of the reaction, the precipitated solids were dissolved into the dichloro-methane, washed with water and dried with sodium sulfate. Removing the solvent by distillation and by refining the resultant product with the use of a silicagel column chromatography (dichloro methane - ethyl acetate), 1.2 g of an yellowish white solids were obtained (yield: 61 %). As a result of MS analysis, it was recognized that the yellowish white solids were identified as the aimed substance and that m/e= 573 for molecular weight of 573.22.
  • 21
  • [ 597554-03-5 ]
  • [ 871320-08-0 ]
  • C42H28 [ No CAS ]
  • 22
  • [ 597554-03-5 ]
  • [ 905947-48-0 ]
  • C56H36 [ No CAS ]
  • 23
  • [ 597554-03-5 ]
  • 3-bromo-5-(naphthalen-1-yl)biphenyl [ No CAS ]
  • C46H30 [ No CAS ]
  • 24
  • [ 597554-03-5 ]
  • 2-(4-bromophenyl)-6-(naphthalen-1-yl)naphthalene [ No CAS ]
  • C50H32 [ No CAS ]
  • 25
  • [ 597554-03-5 ]
  • [ 911390-74-4 ]
  • C52H34 [ No CAS ]
  • 26
  • [ 597554-03-5 ]
  • 1-[1',1":3",1'"-(5'-bromo)terphenyl-3'-yl]pyrene [ No CAS ]
  • C64H40 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 9.5h;Heating / reflux; Under the atmosphere of argon gas, 5 g of obtained 1-[1',1":3",1'"-(5'-bromo)terphenyl-3'-yl]pyrene, and 3.8 g of 10-(naphtherene-2-yl)anthracene-9-boronic acid obtained by a known method, and 0.23 g of tetrakis(triphenylphophine)palladium were dissolved in 80 g of DME, and then 15 ml of 2M sodium carbonate aqueous solution was added therein, and followed by 9.5 hours reflux on heating. After the resultant was left overnight, the precipitated crystal was separated through filtration, and then followed by washing with water, methanol and heated toluene, and 4.1 g of pale yellow solid as the objective compound (AN-43) was obtained (Yield: 57%). By Field Desorption Mass Spectrometry (FD-MS) analysis of the obtained compound, m/z=732 in the case of C58H36=732 was obtained, therefore AN-43 was confirmed.
YieldReaction ConditionsOperation in experiment
52% General procedure: Under N2 protection, ventilation after three times, tetrahydrofuran solution (100ml) and 5-(4-bromophenyl)-1,10-phenanthroline (6.88,20.3 mmol) was added to the three-mouthed bottles, control at a temperature of -78 C, stirring was started after one hour n-butyllithium (2.5M, 8.9ml) was slowly added dropwise to the reaction flask and continue to maintain said temperature, when a white emulsion when stirred for one hour, solution of triisopropyl borate (4.58g, 24.4mmol), and stirring was continued for 3 hours and returned to room temperature, the reaction was continued at room temperature overnight, the reaction progress by TLC.Process: The reaction progress was followed by TLC, to determine the end of the reaction, acidification, water was added, liquid separation (i.e., the upper layer of the reaction solution: tetrahydrofuran), the aqueous layer was extracted three times with methylene chloride, and the resulting solution was evaporated using a rotary evaporator, after addition of petroleum ether to give a white solid by suction filtration, and the resulting white solid product was baked at 50 C in 3 hours to give C-1 (4.39g, 72%).
Under the atmosphere of argon, 7.6 g of 3-bromo-5-(naphthalen-1-yl)biphenyl obtained above, 8 g of 10-(naphthalen-2-yl)anthracene-9-boronic acid obtained in accordance with a conventional process and 0.95 g of tetrakis(triphenylphosphine)palladium were dissolved into 80 ml of 1,2-dimethoxyethane (DME) and 10 ml of toluene.
YieldReaction ConditionsOperation in experiment
83% Under the atmosphere of argon, 3.2 g of 2-(naphthalen-1-yl)naphthalene-6-boronic acid and 2.8 g of 4-bromoiodobenzene were dissolved into 30 ml of toluene, and 0.23 g of tetrakis(triphenyl-phosphine)palladium was added to the obtained solution. After 28 ml of a 2 M aqueous solution of sodium carbonate was added, the resultant mixture was heated under the refluxing condition for 8.5 hours. After the obtained mixture was left standing for one night, the mixture was subjected to extraction with toluene. The extract was washed with a saturated aqueous solution of sodium chloride, and the solvent was removed using an evaporator. The residue was purified in accordance with the silica gel column chromatography (the developing solvent: toluene), and 3.6 g of 2-(4-bromophenyl)-6-(naphthalen-1-yl)naphthalene was obtained as a light yellow solid substance (the yield: 83%). Under the atmosphere of argon, 4.64 g of 10-(naphthalen-2-yl)anthracene-9-boronic acid obtained in accordance with a conventional process and 4.55 g of 2-(4-bromophenyl)-6-(naphthalen-1-yl)naphthalene obtained in accordance with the process described above were dispersed in 40 ml of DME.
YieldReaction ConditionsOperation in experiment
66% The residue was dissolved into heated toluene and recrystallized, and 9.3 g of 4-bromo-3'-(4-phenylnaphthalen-1-yl)biphenyl was obtained as white crystals (the yield: 66%). Under the atmosphere of argon, 6.2 g of 10-(naphthalen-2-yl)anthracene-9-boronic acid obtained in accordance with a conventional process and 7 g of 4-bromo-3'-(4-phenylnaphthalen-1-yl)biphenyl obtained in accordance with the process described above were dispersed in 100 ml of DME.
  • 30
  • [ 597554-03-5 ]
  • [ 204530-94-9 ]
  • 9-(4-(1-naphthyl)phenyl)-10-(2-naphthyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 75℃; for 18h; Under the stream of nitrogen, 5.0 kg of (9-(naphthyl-2-yl)-anthracene-10-yl)boronic acid obtained above in (3), 4.07 kg of 1-(4-bromophenyl-1-yl)naphthalene obtained above in (4), 332 g of tetrakis(triphenylphosphine)palladium, 5.95 kg of potassium carbonate (manufactured by NIPPON SODA Co., Ltd.), 50 liters of water and 50 liters of dimethoxyethane were placed into a reactor having an inner volume of 200 liters, and the reaction was allowed to proceed at 75 C. for 18 hours. After the reaction mixture was cooled to the room temperature, the crystals were separated by filtration and washed with 24 liters of water, 24 liters of methanol and 24 liters of n-heptane and then in 44 liters of n-heptane heated at 50 C. After being cooled to the room temperature, the crystals were separated by filtration. The obtained crystals were purified using a column packed with 25 kg of silica gel and a mixed solvent of hexane and toluene (hexane/toluene=3/1), concentrated under a reduced pressure, filtered after adding 2.5 liters of acetone and washed with 2.5 liters of acetone and 2.5 liters of hexane. After the washed product was dried, the product was purified by sublimation under the condition of a degree of vacuum of 3×10-3 Pa and a temperature of the boat of 270 to 280 C., and 4.81 kg of 9-(naphthyl-2-yl)-10-(4-(naphthyl-1-yl)phenyl-1-yl)anthracene (BH1) was obtained. The purity of BH1 obtained above measured in accordance with the high performance liquid chromatography (HPLC) was 99.98% as the ratio of BH1 peak area to all peak area. When the content of bromine present in BH1 was measured in accordance with the ICP-MS (burning) method, the content was found to be 28 ppm by mass.
  • 31
  • C26H21BO2 [ No CAS ]
  • [ 597554-03-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; hexane; water; at -70 - 5℃; Under the stream of nitrogen, 17.3 kg of 9-bromo-10-(naphthyl-2-yl)anthracene obtained above in (2) and 138 liters of tetrahydrofuran were placed into a 200 liter reactor. The mixture was cooled at -70 C., and 20.4 kg of a 17% by mass hexane solution of n-butyllithium (manufactured by ASIA LITHIUM Co. Ltd.) was added dropwise at a temperature in the range of -64 to -70 C., and the reaction was allowed to proceed at the same temperature for 2 hours. To the obtained reaction mixture, 9.38 kg of trimethyl borate (manufactured by Daihachi Chemical Industry Co., Ltd.) was added dropwise at a temperature in the range of -64 to -70 C., and the reaction was allowed to proceed at the same temperature for 2 hours. To the obtained reaction mixture, 103 liters of a 5 moles/liter hydrochloric acid was added dropwise at a temperature of 5 C. or lower. The obtained product was fractionated at the room temperature, and the organic layer was washed with 60 liters of a 5% by mass solution of sodium hydrogencarbonate and treated by extraction with 60 liters of toluene. The step having the same procedures as those described above was conducted once more, and the products in the two steps were combined. The combined product was washed with 120 liters of a 10% by mass aqueous solution of sodium chloride and concentrated under a reduced pressure. To the concentrated product, 200 liters of n-heptane was added until a slurry was obtained. The crystals in the slurry were separated by filtration, washed in 30 liters of toluene heated at 50 C., cooled to the room temperature, separated by filtration and dried, and 20.3 kg of (9-(naphthyl-2-yl)anthracene-10-yl)boronic acid was obtained.
With hydrogenchloride; In tetrahydrofuran; water; (3) Synthesis of compound <6c>Under nitrogen atmosphere, 9-bromo-10-naphthalene-2-ylanthracene of 12g(31.3 mmol) was melted by THF of 16OmL and then cooled for 30 minutes at -78 C .After n-BuLi (2.5M) of 13.8mL was slowly dropped for 30 minutes at -78 C , themixture was stirred for 30 minutes. After trimethyl borate of 4.2mL (37.6 mmol)was dropped for 15 minutes, the mixture was stirred at room temperatures 20minutes later. The progress of the reaction was verified by TLC. If the reaction didnot continue anymore, the reaction mixture was added with 2M HCl of 10OmL andthen extracted three times with ethlyl acetate of 6OmL. After the extracted mixtureswere mixed together, water was removed therefrom with MgSO4 to distill themixture under reduced pressure. The reactant was recrystallized by toluene and n- <n="61"/>hexane to obtain white crystal of 5.3g (49%).Compound <6c>
  • 32
  • [ 474688-73-8 ]
  • sodium sulfate anhydride [ No CAS ]
  • 1.58M-n-butyllithium [ No CAS ]
  • trimethyl boronic acid ester [ No CAS ]
  • [ 597554-03-5 ]
YieldReaction ConditionsOperation in experiment
65% Synthesis Example 6 (Synthesis of 10-(naphthalene-2-yl)anthracene-9-boronic acid Under argon atmosphere, 150 ml of dehydrated toluene and 150 ml of dehydrated ether were added to 28.8 g of <strong>[474688-73-8]9-bromo-10-(naphthalene-2-yl)anthracene</strong>, and it was cooled to -63 deg C. 58 ml of 1.58M-n-butyllithium/hexane solution was dropped therein. Subsequently, it was stirred at -63 deg C. for 30 minutes, followed by heating up to -10 deg C. It was cooled to -70 deg C. again, and 23.4 ml of trimethyl boronic acid ester/dehydrated ether solution was dropped therein stepwise. After it was stirred at -70 deg C. for 2 hours, it was heated to room temperature steadily. After left over a night, it was acidified by 10% hydrochloric aqueous solution, followed by two time extractions by toluene. The organic layer obtained was washed by saturated salt water and then dried by using sodium sulfate anhydride. After the solvent was removed by distillation, the crystal obtained was recrystallized in toluene/hexane, followed by drying, and then 17 g of 10-(naphthalene-2-yl)anthracene-9-boronic acid was obtained (yield: 65%).
  • 33
  • [ 597554-03-5 ]
  • [ 13720-06-4 ]
  • C58H36 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 8 : Preparation of compound 18; [165]HO18[166] Under N atmosphere, <strong>[13720-06-4]2,6-dibromonaphthalene</strong> (1.5 g, 5.2 mmol), 10-(2-naphthyl) anthracene-9-boronic acid (4.0 g, 11.4 mmol), and Pd(PPh ) (0.3 g, 0.26 mmol) were added to a 2 M aqueous solution of potassium carbonate (80 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 re- crystallized from THF and EtOH to prepare a compound 18 (2.5 g, 66%). MS [M+H] = 733..
  • 34
  • [ 597554-03-5 ]
  • [ 83-53-4 ]
  • 1,4-bis[9-(2-naphthyl)-10-anthryl]naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 15 : Preparation of compound 34; [215][216] Under N atmosphere, 1,4-dibromonaphthalene (1.5 g, 5.2 mmol),<strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (4.0 g, 11.4 mmol), Pd(PPh ) (0.3 g, 0.263 4 mmol) were added to a 2 M aqueous solution of potassium carbonate (80 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 34 (2.5 g, 66%). MS [M+H] = 733 [217]
  • 35
  • [ 597554-03-5 ]
  • [ 7351-74-8 ]
  • C58H36 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 2 : Preparation of compound 2; [108] <n="63"/>[109] Under N atmosphere, <strong>[7351-74-8]1,5-<strong>[7351-74-8]dibromonaphthalene</strong></strong> (1.5 g, 5.2 mmol),10-(2-naphthyl)anthracene-9-boronic acid (4.0 g, 11.4 mmol) and Pd(PPh ) (0.3 g, 0.26 mmol) were added to a 2 M aqueous solution of potassium carbonate (80 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 2 (2.5 g, 66%). MS [M+H] = 733[HO]
  • 36
  • [ 597554-03-5 ]
  • [ 944801-59-6 ]
  • C70H44 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 34 : Preparation of compound 123; [320] <n="88"/>[321] Under N atmosphere, a compound 33a (2.28 g, 5.2 mmol) prepared in 33-A of Example 33, <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (4.0 g, 11.4 mmol), and Pd(PPh ) (0.3 g, 0.26 mmol) were added to a 2 M aqueous solution of potassium3 4 carbonate (80 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 123 (2.5 g, 66%). MS [M+H]+ = 884
  • 37
  • [ 597554-03-5 ]
  • [ 944801-62-1 ]
  • C70H44 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 36 : Preparation of compound 135; [331] <n="89"/>[332] Under N atmosphere, a compound 35a (2.28 g, 5.2 mmol) prepared in 35-A of Example 35, <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (4.0 g, 11.4 mmol), and Pd(PPh ) (0.3 g, 0.26 mmol) were added to a 2 M aqueous solution of potassium carbonate (80 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 135 (2.5 g, 66%). MS [M+H]+ = 884
  • 38
  • [ 597554-03-5 ]
  • [ 944801-65-4 ]
  • C70H44 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 38 : Preparation of compound 147; [342][343] Under N atmosphere, a compound 37a (2.28 g, 5.2 mmol) prepared in 37-A ofExample 37, <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (4.0 g, 11.4 mmol), and Pd(PPh ) (0.3 g, 0.26 mmol) were added to a 2 M aqueous solution of potassium carbonate (80 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 147 (2.5 g, 66%). MS [M+H]+ = 884
  • 39
  • [ 597554-03-5 ]
  • [ 944801-68-7 ]
  • C70H44 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 40 : Preparation of compound 159; [353][354] Under N atmosphere, a compound 39a (2.28 g, 5.2 mmol) prepared in 39-A ofExample 39, <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (4.0 g, 11.4 mmol), and Pd(PPh ) (0.3 g, 0.26 mmol) were added to a 2 M aqueous solution of potassium carbonate (80 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 159 (2.5 g, 66%). MS [M+H]+ = 884
  • 40
  • [ 597554-03-5 ]
  • [ 944801-73-4 ]
  • C64H40 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 24h;Heating / reflux; 41-D. Preparation of compound 170; [365] Under N atmosphere, 41c (3.2 g, 5 mmol), 10-(2-naphthyl)-9-bromo anthracene(2.3 g, 6 mmol), and Pd(PPh ) (0.17 g, 0.15 mmol) were added to a 2 M aqueous3 4 solution of potassium carbonate (20 mL) and THF (50 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, dried over magnesium sulfate, and distilled under reduced pressure. The residue was purified by column chromatography to prepare a compound 170 (2.8 g, 70%). MS [M] = 809
  • 41
  • [ 597554-03-5 ]
  • [ 944801-75-6 ]
  • C64H40 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 24h;Heating / reflux; Example 42 : Preparation of compound 171; [368] <n="93"/>?42a[369] Under N atmosphere, 42a (3.2 g, 5 mmol), 10-(2-naphthyl)-9-bromo anthracene (2.3 g, 6 mmol), and Pd(PPh ) (0.17 g, 0.15 mmol) were added to a 2 M aqueous3 4 solution of potassium carbonate (20 mL) and THF (50 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, dried over magnesium sulfate, and distilled under reduced pressure. The residue was purified by column chromatography to prepare a compound 171 (2.8 g, 70%). MS [M] = 809
  • 42
  • [ 597554-03-5 ]
  • [ 944801-77-8 ]
  • C58H36 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 24h;Heating / reflux; Example 43 : Preparation of compound 174; [372][373] Under N atmosphere, 43a (2.8g, 5 mmol), 10-(2-naphthyl)-9-bromo anthracene (2.3 g, 6 mmol), and Pd(PPh ) (0.17 g, 0.15 mmol) were added to a 2 M aqueous3 4 solution of potassium carbonate (20 mL) and THF (50 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, dried over magnesium sulfate, and distilled under reduced pressure. The residue was purified by column chromatography to prepare a compound 174 (2.6 g, 70%). MS [M] = 809
  • 43
  • [ 597554-03-5 ]
  • [ 19125-84-9 ]
  • C58H36 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; 20-B. Preparation of compound 50; [239] Under N atmosphere, 1,6-dibromonaphthalene (1.5 g, 5.2 mmol), 10-(2-naphthyl) anthracene-9-boronic acid (4.0 g, 11.4 mmol), Pd(PPh ) (0.3 g, 0.26 mmol) were3 4 added to a 2 M aqueous solution of potassium carbonate (80 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 re- crystallized from THF and EtOH to prepare a compound 50 (2.5 g, 66%). MS [M+H] = 733
  • 44
  • [ 597554-03-5 ]
  • [ 944801-42-7 ]
  • C64H40 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 22 : Preparation of compound 66; [250]I r ] _ ?=? - ^ _ _^ ^ ^^[251] Under N atmosphere, a compound 21a (1 g, 2.8 mmol) prepared in 21 -A ofExample 21, <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (2.1 g, 6.1 mmol), Pd(PPh ) (0.16 g, 0.14 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 66 (1.8 g, 78%). MS [M] = 808
  • 45
  • [ 597554-03-5 ]
  • [ 952604-27-2 ]
  • C64H40 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; 24-B. Preparation of compound 78; [262] Under N atmosphere, a compound 24a (1 g, 2.8 mmol) prepared in 24-A,<strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (2.1 g, 6.1 mmol), and Pd(PPh 3 ) 4 (0.16 g,0.14 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 78 (1.7 g, 75%). MS [M] = 808
  • 46
  • [ 597554-03-5 ]
  • [ 952604-26-1 ]
  • [ 944801-51-8 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 27 : Preparation of compound 86; [280]Ir i I " ^~ 2 ^ ~ Z[281] Under N atmosphere, a compound 26a (1 g, 2.8 mmol) prepared in 26-A ofExample 26, <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (2.1 g, 6.1 mmol), and Pd(PPh ) (0.16 g, 0.14 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 86 (1.8 g, 78%). MS [M] = 808
  • 47
  • [ 597554-03-5 ]
  • [ 944801-53-0 ]
  • C64H40 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 29 : Preparation of compound 90; [291][292] Under N atmosphere, a compound 28a (1 g, 2.8 mmol) prepared in 28-A ofExample 28, <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (2.1 g, 6.1 mmol), and Pd(PPh <n="85"/>) (0.16 g, 0.14 mmol) were added to a 2 M aqueous solution of potassium carbonate4(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 90 (1.8 g,78%). MS [M] = 808 [293]
  • 48
  • [ 597554-03-5 ]
  • [ 944801-57-4 ]
  • C70H44 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux; Example 32 : Preparation of compound 111; [309](I 1[310] Under N atmosphere, a compound 31a (2.28 g, 5.2 mmol) prepared in 31-A ofExample 31, <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> (4.0 g, 11.4 mmol), and Pd(PPh ) (0.3 g, 0.26 mmol) were added to a 2 M aqueous solution of potassium <n="87"/>carbonate (80 rnL) and anisole (100 rnL). 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 111 (2.5 g, 66%). MS [M+H]+ = 884
  • 49
  • [ 597554-03-5 ]
  • [ 31409-84-4 ]
  • [ 950855-69-3 ]
YieldReaction ConditionsOperation in experiment
60% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; Synthesis Example 1: Synthesis of Compound (1); [Show Image] In a stream of argon, 3.0 g (6.6 mmol) of Intermediate 1, 2.5 g (8.9 mmol) of 10-naphthalen-2-yl-anthracene-9-boronic acid, 0.16 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium(0), 30 mL of 1,2-dimethoxyethane, and 11 mL (22 mmol) of a 2-M aqueous solution of sodium carbonate were added to a 300-mL three-necked flask, and the whole was refluxed under heat for 8 hours. After the completion of the reaction, dichloromethane was added, and the resultant was sufficiently washed with water and dried with magnesium sulfate. After that, the solvent was removed by distillation with a rotary evaporator. The resultant coarse crystal was purified by means of silica gel column chromatography (developing solvent: chloroform), and was then washed with 100 mL of methanol, whereby 2.6 g of a pale yellow powder were obtained. The powder was identified as Compound (1) by field desorption mass spectrometry (FD-MS) (60% yield).
  • 50
  • [ 597554-03-5 ]
  • 2-(4-Bromo-3-methylphenyl)-4,6-di-2-pyridinyl(1,3,5)triazine [ No CAS ]
  • [ 1008522-39-1 ]
YieldReaction ConditionsOperation in experiment
40% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 10h;Heating / reflux; Example 4 (Synthesis of 2-[3-methyl-4-[10-( naphthalene-2-yl)anthracen-9-yl]phenyl]-4,6-di-2-pyridinyl(1,3,5)triazine (hereinafter referred to as betaNAPPy-TRZ) (Compound 7)); 1.0 g of 2-(4-Bromo-3-methylphenyl)-4,6-di-2-pyridinyl(1,3,5)triazine, 1.28 g of 10-( naphthalene-2-yl)anthracene-9-boronic acid, 7.2 ml of a 1M potassium carbonate aqueous solution, 0.06 g of tetrakis(triphenylphosphine)palladium(0), 23 ml of toluene, and 8 ml of ethanol were added and the whole was stirred for 10 hours under heating and refluxing. After cooling to room temperature, water was added thereto for washing, thereby obtaining a crude product. The resulting crude product was dissolved in chloroform and purified by column chromatography (carrier: NH silica gel, eluent: chloroform/hexane) to obtain 1.22 g (yield 40%) of yellow crystals of betaNAPPy-TRZ (Compound 7). The results of NMR analysis (CDCl3) were as follows. 9.005 (2H), 8.919-8.835 (4H), 8.114-7.932 (6H), 7.777-7.758 (2H), 7.753-7.550 (8H), 7.381-7.278 (4H), 2.140 (3H).
  • 51
  • [ 597554-03-5 ]
  • [ 1191076-26-2 ]
  • [ 1191076-03-5 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 12h;Heating; Synthesis Example 4: Synthesis of Compound 8; Compound 8 was synthesized according to Reaction Scheme 3 below: [Show Image] Intermediate 8d was synthesized by reacting Compound 1d with 4-bromophenylboronic acid through a Suzuki coupling reaction. 6.27 g (18 mmol) of Intermediate 8c and 4.67 g (15 mmol) of Intermediate 8d were added to a mixed solvent of THF and K2CO3 solution, 0.52 g (3 mol%) of Pd(PPh3)4 was added thereto while stirring, and the mixture was heated for 12 hours. The mixture was cooled to room temperature and subject to extraction using dichloromethane. Then, an organic layer was collected, and the solvent was removed by drying the organic layer using anhydrous magnesium sulfate under reduced pressure. The resulting product was filtered using column chromatography (ethyl acetate:dichloromethane=3:7) to obtain 6.8 g of yellow solid Compound 8 (Yield: 85%). 1H NMR (500MHz, CDCl3) delta 8.79(dd, 2H), 8.41(d, 2H), 8.12-8.08(m, 3H), 8.06-7.93(m, 5H), 7.87-7.79(m, 3H), 7.74(dd, 2H), 7.69-7.60(m, 5H), 7.38-7.31(m, 4H).
  • 52
  • [ 597554-03-5 ]
  • [ 955959-84-9 ]
  • [ 1084334-29-1 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 10h;Reflux; Inert atmosphere; [Example-of-Synthesis 1] Synthesis of Compound 1 [Show Image] Under an argon atmosphere, 30 mL of dimethoxyethane (DME) and 15 mL of a 2-M aqueous solution of sodium carbonate were added to 3.22 g (10.0 mmol) of <strong>[955959-84-9]4-(4-bromophenyl)dibenzofuran</strong>, 3.83 g (11.0 mmol) of 10-(2-naphthyl)anthracene-9-boronic acid, and 0.231 g (0.200 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was refluxed under heat for 10 hours. After the completion of the reaction, the resultant was cooled to room temperature. The precipitated solid was taken by filtration, washed with methanol, water, and methanol in the stated order, and dried under reduced pressure. The resultant solid was recrystallized with toluene, whereby 4. 20 g of a pale yellow crystal were obtained. Mass spectral analysis confirmed the following: the crystal was the target product and had an m/e of 546, which was indicative of the molecular weight of the target product, i.e., 546.20.
  • 53
  • [ 597554-03-5 ]
  • 2-(3’-bromophenyl)benzofuran [ No CAS ]
  • [ 1084334-21-3 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 10h;Reflux; Inert atmosphere; (1-2) Synthesis of Compound X-1 Under an argon atmosphere, 30 mL of dimethoxyethane (DME) and 15 mL of a 2-M aqueous solution of sodium carbonate were added to 2.73 g (10.0 mmol) of 2-(3-bromophenyl)benzo[b]furan, 3.83 g (11.0 mmol) of <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong>, 0.231 g (0.200 mmol) of tetrakis (triphenylphosphine) palladium(0), and the mixture was refluxed under heat for 10 hours. After the completion of the reaction, the resultant was cooled to room temperature. The precipitated solid was taken by filtration, washed with methanol, water, and methanol in the stated order, and dried under reduced pressure. The resultant solid was recrystallized with toluene, whereby 4.20 g of a pale yellow crystal were obtained. Mass spectral analysis confirmed the following: the crystal was the target product and had an m/e of 496, which was indicative of the molecular weight of the target product, i.e., 496.18.
  • 54
  • [ 597554-03-5 ]
  • [ 122048-53-7 ]
  • [ 1152130-47-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 8h;Inert atmosphere; Reflux; Example 2 Compound 2 was synthesized according to the following synthesis scheme. [Show Image] Under an argon atmosphere, 3.57g of the 10-bromobenzo[g]chrysene which had been prepared in Synthesis Example 2, 4.18g of <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> which had been synthesized by a known method, 0.231g of tetraxis(triphenylphosphine)palladium(0), 40 mL of toluene and 20 mL of a 2M aqueous solution of sodium carbonate were placed in a flask. The resultant was refluxed with stirring for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and an organic phase which had been separated was washed with water and then with saturated brine, and dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by a silica gel column chromatography, whereby 4.06g of light yellow crystals were obtained. As a result of mass spectrometry, the resulting crystals were confirmed to be the above-mentioned compound 2.
  • 55
  • [ 597554-03-5 ]
  • [ 89523-51-3 ]
  • [ 1155911-75-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 8h;Reflux; Under an argon atmosphere, 3.07g of the <strong>[89523-51-3]5-bromobenzo[c]phenanthrene</strong> which had been prepared in Synthesis Example 1, 4.18g of 10-(2-naphthyl)anthracene -9-boronic acid which had been synthesized by a known method, 0.231 g of tetraxis(triphenylphosphine)palladium(0), 40 mL of toluene and 20 mL of a 2M aqueous solution of sodium carbonate were charged. The resultant was refluxed with stirring for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and an organic phase which had been separated was washed with water and saturated brine sequentially, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by a silica gel column chromatography, whereby 4.13g of pale yellow crystals were obtained. As a result of mass spectrometry, the resulting crystals were confirmed to be the above-mentioned compound 1. The compound 1 had an m/e value of 530 with respect to a molecular weight of 530.20.
  • 56
  • [ 597554-03-5 ]
  • 2-triphenylenyl trifluoromethanesulfonate [ No CAS ]
  • [ 1158495-80-7 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 8h;Reflux; Inert atmosphere; Example 1 The following compound 1 was synthesized from intermediate A by the following reaction. [Show Image] Under an argon atmosphere, 3.76 g of intermediate A obtained in Synthesis Example 1, 4.18 g of <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> which was synthesized by a known method, 0.231 g of tetrakis(triphenylphosphine)palladium (0), 40 mL of toluene and 20 mL of a 2M sodium carbonate aqueous solution were placed in a flask and refluxed with stirring for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and an organic phase was washed with water and saturated brine sequentially and dried with magnesium sulfate. Magnesium sulfonate was filtered out, and then the organic phase was concentrated. The resulting residue was purified by means of a silica gel column chromatography to obtain 4.35 g of a pale yellow crystal. As a result of mass spectrum analysis, m/z=530, and it was confirmed that the product of the synthesis was Compound 1 (molecular weight: 530.20).
  • 57
  • [ 474688-73-8 ]
  • [ 597554-03-5 ]
YieldReaction ConditionsOperation in experiment
72% d. Preparation of Intermediate E; Into a solution of 9-bromo-10-naphthalen-2-yl-anthracene (compound D, 12.0 g, 1 eq) dissolved in anhydrous THF (200 mL), was added slowly n-BuLi (2.5 M in hexane, 12.4 mL, 1.2 eq) at -78 C. under N2. The deep red reaction mixture was stirred for 2 hr. Triisopropylborate (5.89 g, 1.2 eq) was added dropwise into the cooled solution and stirred at this temperature for 0.5 h. The solution became bright yellow over this time. The reaction was warmed up to room temperature and stirred for 1 hr. After quenching the mixture with 20% HCl solution (100 mL) for 1 hr the organic layer was separated and the aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layer was dried over anhydrous sodium sulfate, then concentrated under reduced pressure to a yellow solid. This solid was suspended in a small amount of EtOAc and the precipitated solid was filtered to give 7.8 g of compound E (72%).
Under the atmosphere of argon, 588 g of the crystals obtained above, 4.5 liters of dehydrated ether (manufactured by HIROSHIMA WAKO Co., Ltd.) and 4.5 liters of dehydrated toluene (manufactured by HIROSHIMA WAKO Co., Ltd.) were placed into a 20 liter flask, and the resultant mixture was cooled at -64 C. in a dry ice bath. To the cooled mixture, 1.2 liters of a 1.6 M hexane solution of butyllithium (manufactured by HIROSHIMA WAKO Co., Ltd.) was added dropwise over 30 minutes, and the reaction was allowed to proceed at -64 C. for 2 hours. To the resultant reaction mixture, 866 g of triisopropyl borate (manufactured by TOKYO KASEI Co., Ltd.) was added dropwise over 20 minutes. After the addition was completed, the temperature was adjusted at the room temperature, and the reaction mixture was stirred for 12 hours. After the resultant reaction mixture was cooled with ice, 4 liters of 2 N hydrochloric acid was added at a temperature of 10 C. or lower, and 1 liter of toluene was added. The organic phase separated from the resultant mixture was dried with sodium sulfate and concentrated under a reduced pressure. Hexane was added to the resultant solution, and formed crystals were separated by filtration. The obtained crystals were dissolved into 5 liters of tetrahydrofuran. To the resultant solution, 500 ml of concentrated hydrochloric acid and 5 g of tetrabutylammonium bromide were added, and the resultant mixture was stirred for 12 hours. The formed crystals were separated by filtration and dried, and 431 g of crystals were obtained.Since m/z=348 in the field desorption mass analysis (FD-MS) of the obtained compound, which corresponded to C24H17BO2=348, the compound was identified to be 10-(2-naphthynanthracene-9-boric acid (the yield: 47%).
  • 58
  • [ 597554-03-5 ]
  • [ 323195-51-3 ]
  • [ 1245719-24-7 ]
YieldReaction ConditionsOperation in experiment
76% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene;Reflux; Inert atmosphere; e. Preparation of Compound H1; To the solution of 3-iodo-1-phenylindazole (1.1 g, 1 eq) in toluene (30 mL) and ethanol (15 mL) were added 10-(2-naphthyl)-anthracene-9-boronic acid (compound E, 1.43 g, 1.2 eq), Pd(PPh3)4 (0.2 g, 0.05 eq), and Na2CO3 (2.18 g, 6 eq), followed by the addition of 25 ml of degassed water. The mixture was refluxed overnight under N2, and then it was extracted with EtOAc (2×50 ml). The combined organic layer was washed with water, dried with Na2SO4, and concentrated under reduced pressure. By silica gel column chromatography (20% DCM/hexane, then 10% EtOAc/hexane) compound H1 (1.29 g, 76%) was obtained as a pale yellow solid.
  • 59
  • [ 109-04-6 ]
  • [ 597554-03-5 ]
  • [ 1310481-52-7 ]
  • 60
  • [ 185112-61-2 ]
  • [ 597554-03-5 ]
  • [ 1310481-54-9 ]
  • 61
  • [ 597554-03-5 ]
  • [ 212385-73-4 ]
  • [ 1310481-55-0 ]
  • 62
  • [ 597554-03-5 ]
  • [ 57102-42-8 ]
  • 9-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-9H-carbazole [ No CAS ]
  • 63
  • [ 597554-03-5 ]
  • [ 19493-44-8 ]
  • [ 1310481-53-8 ]
  • 64
  • 2, 7, 12-tribromo-5,5',10,10',15,15'-hexaethyltruxene [ No CAS ]
  • [ 597554-03-5 ]
  • [ 1246465-82-6 ]
  • 65
  • [ 597554-03-5 ]
  • [ 1246465-80-4 ]
  • [ 1246465-81-5 ]
  • 66
  • [ 597554-03-5 ]
  • [ 22082-99-1 ]
  • [ 667940-24-1 ]
YieldReaction ConditionsOperation in experiment
47% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 24h;Inert atmosphere; Reflux; Example 1 Synthesis of a Compound (AN8); Under the atmosphere of argon, a solution prepared by dissolving 5.98 g of 10-(2-naphthyl)anthracene-9-boric acid obtained in Synthesis Example 1, 4.05 g of 2-(4-bromophenyl)naphthalene obtained in Synthesis Example 2, 0.33 g of tetrakis(triphenylphosphine)palladium(0) (manufactured by TOKYO KASEI Co., Ltd.), 60 ml of 1,2-dimethoxyethane (manufactured by HIROSHIMA WAKO Co., Ltd.) and 4.55 g of sodium carbonate (manufactured by HIROSHIMA WAKO Co., Ltd.) into 21 ml of water was placed into a 300 ml flask, and the resultant mixture was stirred for 24 hours while being heated under the refluxing condition. After the reaction was completed, the reaction mixture was cooled to the room temperature, and formed crystals were separated by filtration. The obtained compound was purified in accordance with the column chromatography, and 3.4 g of a light yellow solid substance was obtainedSince m/z=506 in FD-MS of the obtained compound, which corresponded to C40H26=506, the compound was identified to be AN8 (the yield: 47%).
45% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene;Reflux; General procedure: In a round-bottom flask, 37.3 g (132 mmol) of 1-bromo-4-iodobenzene, 14.2 g (125 mmol) of (1H-1,2,4-triazol-1-yl) boronic acid,Potassium carbonate 36.6g (264mmol), Pd (PPh3) 4 3g (2mmol), water 70ml, toluene 180ml and tetrahydrofuran 180ml was added and refluxed.After the reaction, the layer was separated to remove the aqueous layer and the organic layer was concentrated under reduced pressure.Column chromatography was used to obtain 22 g of 1- (4-bromophenyl) -1H-1,2,4-triazole (75% yield).
  • 67
  • [ 597554-03-5 ]
  • [ 667940-21-8 ]
  • [ 667940-26-3 ]
YieldReaction ConditionsOperation in experiment
40% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 24h;Inert atmosphere; Reflux; Example 2 Synthesis of a Compound (AN10); Under the atmosphere of argon, a solution prepared by dissolving 5.98 g of 10-(2-naphthyl)anthracene-9-boric acid obtained in Synthesis Example 1, 5.13 g of 3-(4-bromophenyl)fluoranthene obtained in Synthesis Example 3, 0.33 g of tetrakis(triphenylphosphine)palladium(0) (manufactured by TOKYO KASEI Co., Ltd.), 60 ml of 1,2-dimethoxyethane (manufactured by HIROSHIMA WAKO Co., Ltd.) and 4.55 g of sodium carbonate (manufactured by HIROSHIMA WAKO Co., Ltd.) into 21 ml of water was placed into a 300 ml flask, and the resultant mixture was stirred for 24 hours while being heated under the refluxing condition. After the reaction was completed, the reaction mixture was cooled to the room temperature, and formed crystals were separated by filtration. The obtained compound were purified in accordance with the column chromatography, and 3.3 g of a light yellow solid substance was obtainedSince m/z=580 in FD-MS of the obtained compound, which corresponded to C46H28=580, the compound was identified to be AN10 (the yield: 40%).
  • 68
  • [ 474688-73-8 ]
  • [ 121-43-7 ]
  • [ 597554-03-5 ]
YieldReaction ConditionsOperation in experiment
89% Under nitrogen, 3.83 g (10 mmol) of Intermediate-7 was dissolved in 40 ml of anhydrous THF, the temperature of the reaction was lowered to -78 C and 2.5 M n-After 4 ml of BuLi was slowly added dropwise, the reaction was stirred at 0 & lt; 0 & gt; C for 1 hour. Then, the temperature of the reactant was adjusted to -78 And 12.47 g (12 mmol) of trimethyl borate was added dropwise thereto, followed by stirring at room temperature for 12 hours. When the reaction is terminated2N-HCl aqueous solution was added thereto, stirred for 30 minutes, and extracted with ether. After the water in the organic layer was removed with anhydrous MgSO4 and the filtrate was subjected to filtration under reduced pressure, the organic solvent was concentrated to obtain the resulting compound. Hex: MC = 3:1 to obtain 3.10 g (89%) of intermediate-10.
71% The compound B-1 (6.86 g, 17.9 mmol) was dissolved in tetrahydrofuran (150 mL), the temperature was lowered to -78C, and 1.7M tert-butyllithium (t-BuLi)(10.5 ml, 17.9 mmol) was slowly added thereto. After it was agitated for 1 hour at the same temperature, trimethyl borate (B(OCH3)3) (3.72 g, 35.8 mmol) was added thereto, and it was agitated for 3 hours while the temperature was slowly increased to normal temperature. 2N hydrochloric acid aqueous solution (30 ml) was added to the reaction mixture and agitated for 1.5 hours at normal temperature. The generated precipitate was filtered and sequentially washed with water and ethylether, and dried under the vacuum. It was dispersed in ethylether, agitated for 2 hours, filtered, and dried to prepare the compound B-2 (4.44 g, 71%). MS:[M+H]+=349
71% Compound B-1 (6.86g,17.9mmol) was dissolved in tetrahydrofuran (150mL), 1.7M tert-butyllithium(t-BuLi) (10.5mL, 17.9mmol) was addedslowly at -78? to lower the temperature. After stirring for one hour at thesame temperature, trimethyl borate (B (OCH3) 3, 3.72g, 35.8mmol added), and thetemperature was slowly raised to room temperature, and stirred for 3 hours. Tothe reaction mixture was added 2N aqueous hydrochloric acid solution (30mL) andstirred at room temperature for 1.5 hours. The resulting precipitate wasfiltered, washed with water and ethyl ether and then dried under vacuum. Themixture was stirred for two hours, filtered and dried to obtain compound B-2 (4.44g,yield 71%).
  • 69
  • [ 597554-03-5 ]
  • [ 589-87-7 ]
  • [ 936854-62-5 ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 5h;Reflux; After the compound B-2 (3.48 g, 10.0 mmol) and 1-bromo-4-iodobenzene (3.4 g, 12.0 mmol) were dissolved in tetrahydrofuran (100 mL), 2M potassium carbonate aqueous solution (20 mL) was added thereto, and tetrakistriphenylphosphino palladium (Pd(PPh3)4 (0.23 g, 2 mol%) was put thereinto, agitated and refluxed for 5 hours. The temperature was cooled to normal temperature, and the produced solid was filtered. The filtered solid was dissolved in chloroform, and dried with anhydrous magnesium sulfate, and filtered. The reaction solution was concentrated under the reduced pressure and recrystallized with tetrahydrofuran and ethanol to prepare the compound B-3 (3.30 g, 72%). MS.[M+H]+=460
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Reflux; Compound B-2 (3.48g,10.0mmol) and 1-bromo-4-iodobenzene (1-bromo-4-iodobenzene, 3.4g, 12.0mmol) was dissolved in tetrahydrofuran (100mL), 2M aqueous potassium carbonate solution (20mL)was added and tetrakistriphenylphosphine palladium (Pd (PPh3) 4, (0.231g,2mol%) was added and refluxed under stirring for 5 hours. The resulting mixturewas cooled to room temperature, filtered, concentrated under reduced pressure, andrecrystallized with ethanol and tetrahydrofuran to obtain compound B-3 (3.30 g,yield 72%).
  • 72
  • [ 597554-03-5 ]
  • [ 1226815-17-3 ]
  • [ 1226815-19-5 ]
  • 73
  • 1-(3-iodophenyl)naphthalene [ No CAS ]
  • [ 597554-03-5 ]
  • [ 910458-11-6 ]
  • 74
  • [ 597554-03-5 ]
  • [ 1178861-69-2 ]
  • [ 1178861-70-5 ]
  • 75
  • [ 597554-03-5 ]
  • [ 1271733-35-7 ]
  • [ 1178861-96-5 ]
  • 76
  • [ 597554-03-5 ]
  • [ 1271733-36-8 ]
  • [ 1271733-31-3 ]
  • 77
  • [ 597554-03-5 ]
  • [ 1250255-82-3 ]
  • [ 1250255-60-7 ]
  • 78
  • [ 597554-03-5 ]
  • [ 76129-22-1 ]
  • [ 1271733-30-2 ]
  • 79
  • [ 597554-03-5 ]
  • [ 198964-46-4 ]
  • [ 1335302-25-4 ]
  • 80
  • [ 597554-03-5 ]
  • [ 428865-53-6 ]
  • [ 1335302-26-5 ]
  • 83
  • [ 597554-03-5 ]
  • [ 10485-09-3 ]
  • [ 1236139-26-6 ]
YieldReaction ConditionsOperation in experiment
84% With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 18h;Reflux; 4 g of compound S1 (11.4 mmol), 2.69 g of compound A (13.8 mmol), 265 mg of tetrakistriphenylphosphinpalladium (Pd[PPh3]4, 0.229 mmol), and 4.87 g of potassium phosphate (K3PO4, 22.9 mmol) were put into 100 mL of water and 100 ml of THF, and refluxed and agitated. After 18 hours, the temperature was decreased to normal temperature, and the organic layer was separated. 4g of compound 10 was obtained at a yield of 84% by removing the solvent and recrystallizing the generated solid in chloroform/methanol. [M+H] = 419
  • 84
  • [ 597554-03-5 ]
  • [ 3333-24-2 ]
  • [ 1236139-18-6 ]
YieldReaction ConditionsOperation in experiment
62% With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 18h;Reflux; 4 g of compound S1 (11.4 mmol), 2.4 g of compound A (11.4 mmol), 265 mg of tetrakistriphenylphosphinpalladium (Pd[PPh3]4, 0.229 mmol), and 4.87 g of potassium phosphate (K3PO4, 22.9 mmol) were put into 100 mL of water and 100 ml of THF, and refluxed and agitated. After 18 hours, the temperature was decreased to normal temperature, and the organic layer was separated. 3.08 g of compound 2 was obtained at a yield of 62% by removing the solvent and recrystallizing the generated solid in chloroform/methanol. [M+H] = 433
  • 85
  • [ 597554-03-5 ]
  • 6-iodo-benzo[1,2-b:5,4-b’]bisbenzofuran [ No CAS ]
  • [ 1256544-35-0 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Inert atmosphere; Reflux; Example 1; [Show Image] In the atmosphere of argon, 3.84g of intermediate (B), 3.83g of <strong>[597554-03-5]10-(2-naphthyl)anthracene-9-boronic acid</strong> which was synthesized by a known method, 0.231g of tetrakis(triphenylphosphine)palladium (0), 40 mL of 1,2-dimethoxyethane and 20 mL of a 2M aqueous sodium carbonate solution were charged. The resulting mixture was stirred under reflux for 8 hours. After cooling to room temperature, deposited solids were filtered out. The solids thus obtained were washed with water and methanol, recrystallized from toluene, whereby 4.20g of pale yellow solids of compound 1 were obtained. As a result of mass spectroscopy, it was confirmed that the solids were an intended product having an m/e of 560 relative to the molecular weight of 560.18.
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