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Structure of 867044-33-5

Chemical Structure| 867044-33-5

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Product Details of [ 867044-33-5 ]

CAS No. :867044-33-5
Formula : C19H15BN2O2
M.W : 314.15
SMILES Code : OB(C1=CC=C(N2C(C3=CC=CC=C3)=NC4=CC=CC=C24)C=C1)O
MDL No. :MFCD11977298
InChI Key :RCOAUYBPVRIYBG-UHFFFAOYSA-N
Pubchem ID :23160219

Safety of [ 867044-33-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 867044-33-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 24
Num. arom. heavy atoms 21
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 96.33
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

58.28 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.66
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.37
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.61
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.4
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.01

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.54
Solubility 0.009 mg/ml ; 0.0000286 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.57
Solubility 0.0084 mg/ml ; 0.0000267 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-5.99
Solubility 0.000319 mg/ml ; 0.00000102 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.62 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.51

Application In Synthesis of [ 867044-33-5 ]

* 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 [ 867044-33-5 ]

[ 867044-33-5 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 561064-15-1 ]
  • [ 867044-33-5 ]
  • 2,6-bis[4-(2-phenyl-1H-benzimidazol-1-yl)-phenyl]-9,10-di(2-naphthyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; 2.0 g (3.4 mmol) of 2,6-dibromo-9,10-di(2-naphthyl)anthracene, 2.4 g (7.5 mmol) of <strong>[867044-33-5]4-(2-phenyl-1H-benzimidazol-1-yl)phenylboronic acid</strong>, and 0.16 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 30 mL of 1,2-dimethoxyethane. Then, 15 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. The resultant was stood to cool. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 2.4 g of a greenish white solid (73% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 966 with respect to a molecular weight of 966.37.
  • 2
  • [ 760212-58-6 ]
  • [ 867044-33-5 ]
YieldReaction ConditionsOperation in experiment
46% In an argon atmosphere, 10 g (29 mmol) of 1-(4-bromophenyl)-phenyl-1H-benzimidazole were dissolved into 100 mL of dehydrated THF, and the temperature of the solution was cooled to -78 C. Then, 20 mL of n-butyllithium (in hexane, 1.6 mol/L) were dropped. After the mixture had been stirred at -78 C for 1 hour, the temperature of the mixture was increased to 0C. The temperature of the mixture was cooled to -78 C again, and 9.7 mL (87 mmol) of trimethoxyborane were dropped. The mixture was stirred at -78 C for 1 hour, and was then stirred at room temperature for 2 hours. 100 mL of 10-mass% hydrochloric acid were added, and the whole was stirred for 1 hour, followed by filtration. The organic layer of the filtrate was washed with a saturated sodium chloride solution and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of silica gel column chromatography to obtain 4.2 g of 4-(2-phenyl-1H-benzimidazol-1-yl)phenylboronic acid (46% yield).
  • 3
  • [ 867044-33-5 ]
  • [ 867044-34-6 ]
  • 9,10-di(2-naphthyl)-2-(2-phenyl-1H-benzimidazol-1-yl)-6-[4-(2-phenyl-1H-benzimidazol-yl)-phenyl]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 8h;Heating / reflux; 2.5 g (3.6 mmol) of 2-bromo-9, 10-di (2-naphthyl)-6- (2-phenyl-1H-benzimidazol-1-yl)anthracene, 1.4 g (4.3 mmol) of 4-(2-phenyl-1H-benzimidazol-1-yl)phenyl boronic acid, and 0.16 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 30 mL of 1,2-dimethoxyethane. Then, 15 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. The resultant was stood to cool. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 2.4 g of a greenish white crystal (76% yield). Mass spectral analysis confirmed that the crystal was a target product. The crystal had an m/e of 890 with respect to a molecular weight of 890.34.
  • 4
  • [ 867044-33-5 ]
  • 3-(2'-bromo-[1,1'-biphenyl]-2-yl)-9-phenyl-9H-carbazole [ No CAS ]
  • C49H33N3 [ No CAS ]
  • 5
  • [ 867044-33-5 ]
  • 2,10-dibromo-6-(2,4,6-trimethylphenyl)-6H-6-borabenzo[cd]pyrene [ No CAS ]
  • C65H45BN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.2% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 100℃; for 3h;Inert atmosphere; Synthesis of Compound (5): Under the protection of nitrogen, To a 250ml three-necked round flask was added 2,10-dibromo-6-(2,4,6-trimethylphenyl)-6H-6-borabenzo[cd]pyrene (5.14g, 0.01mol), Intermediate 5-D (6.90g, 0.022mol), 0.35g (0.0003mol) Pd (PPh3) 4,Toluene 75ml, 75ml ethanol, and 50ml concentration of the potassium carbonate solution 2mol·L-1. Stirred at 100C. After 3h the reaction mixture was cooled, the organic phase was separated, and the organic phase washed with water 3 times and dried with anhydrous Mg2SO4, the organic solvent was removed by rotary evaporation to give the crude product.The crude product was purified by silica gel column chromatography separation, methylene chloride / petroleum ether as eluent to give a white crystalline solid 7.10g. Yield 79.2%.
  • 6
  • [ 106-40-1 ]
  • [ 867044-33-5 ]
  • 7
  • [ 1493-27-2 ]
  • [ 867044-33-5 ]
  • 8
  • [ 58476-59-8 ]
  • [ 867044-33-5 ]
  • 9
  • [ 100953-52-4 ]
  • [ 867044-33-5 ]
  • 10
  • [ 760212-58-6 ]
  • [ 5419-55-6 ]
  • [ 867044-33-5 ]
YieldReaction ConditionsOperation in experiment
93.41% In a 1000 ml three-necked flask, equipped with mechanical stirring, Ar gas protection, add 25. lg of the bromine synthesized in the third step (molecular weight 348, 0.072 mol 1), 300 ml of anhydrous THF, cooled to -78 C, stirred 35ml of BuLi (2 · 4M, 0.084mol) was added dropwise, the temperature was maintained at _78 C, and after stirring for 10 min, 40 ml of B(0iPr) 3 (molecular weight 188.07, specific gravity 0.9574, 0.204 mol) was added dropwise at -78 C. After stirring to room temperature (with 3 hrs), dilute acid is added to hydrolyze, the aqueous layer is separated, neutralized to neutrality, sodium chloride is added, hydrazine HF dissolved in water is distilled off under reduced pressure, and a white solid is precipitated and filtered to obtain a product. 21 g of solid product, yield 93.41%.
80% Under nitrogen protection,In a 1000ml three-neck bottle,30 g (85.96 mmol, 1 eq) of the compound 1- (4-bromophenyl) -2-phenyl-1H-benzo [d] imidazole was added to 300 mL of tetrahydrofuran,Cooling down to minus 78 degrees,39.4 mL (94.56 mmol, 1.1 eq) of n-BuLi was slowly added dropwise to the above reaction solution,Incubation reaction for 1.5h,Subsequently, 32.3 g (171.92 mmol, 2 eq) of triisopropyl borate was slowly added dropwise to the above reaction solution,Naturally warmed to room temperature and stirred overnight to stop the reaction,Add 100 mL of a 1 mol / L dilute hydrochloric acid solution and stir at room temperature for 1 h.The layers were separated, and the aqueous phase was extracted with 200 mL of dichloromethane * 1. The organic phases were combined.Spin-drying gave 21.67 g of a white solid with a yield of 80%.
76.8% With n-butyllithium; In tetrahydrofuran; at -78℃; Synthesis of Intermediate 5-D: In a 250ml three-necked round flask, added was Intermediate 5-C(11.5g, 0.03mol), and 120ml dried THF that underwent treatment with Na /Benzophenone. Liquid nitrogen was used to cool reaction to -78C. While stirring, slowly added dropwise 14.5ml of n-butyllithium (0.036mol, 2.5mol·L-1), and Triisopropyl borate 9.96ml (8.12g, 0.043mol). After the addition was completed, stirred to room temperature. Adding an appropriate amount of dilute hydrochloric acid, hydrolysis, extraction with ethyl acetate, the combined organic phases. The organic solvent was removed by rotary evaporation to give the crude product. After recrystallization from ethanol to give a white solid 7.23g, yield 76.8%.
  • 11
  • [ 867044-33-5 ]
  • 9,9'-((2-bromo-[1,1'-biphenyl]-4,4'-diyl)bis(methylidenyl))bis(9H-fluorene) [ No CAS ]
  • C59H38N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; for 8h;Inert atmosphere; Reflux; 10g (17mmol) of the intermediate step, 6.4g (20.5mmol) of (4- (2-phenyl -1H- benzo [d] imidazol-1-yl) phenyl) boronic acid, 197mg (0.17mmol) of a palladium catalyst Pd (PPh3)4And 34ml of 1M aqueous sodium carbonate solution, then add 30ml of toluene and 15ml of ethanol, under nitrogen, was stirred at reflux temperature for 8 hours, cooled to room temperature, extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to dryness, isolated and purified by a silica gel column with petroleum ether - ethyl acetate, and then recrystallized from ethanol to give 6.5g yellow solid, yield 49%.
  • 12
  • [ 867044-33-5 ]
  • C34H21BrN2 [ No CAS ]
  • C53H34N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Inert atmosphere; Heating; In a three-necked flask,Intermediate 1-3 (3 g, 5.6 mmol) was added,Intermediate 1-4 (2 g, 5.6 mmol),Potassium carbonate (1.8 g, 11.2 mmol),Tetrakistriphenylphosphine palladium (0.1 g),Tetrahydrofuran (50 ml) and water (20 ml)The mixture was heated under nitrogen for 5 hours,cool down,filter,The crude product was recrystallized from tetrahydrofuran and ethanol,The product was obtained in 3.5 g, yield 86%.
  • 13
  • [ 867044-33-5 ]
  • [ 1301161-41-0 ]
  • 3-(2-phenyl-N-4-phenylbenzimidazolyl)-N,N'-dicarbazolyl-4,4'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 24h;Inert atmosphere; Reflux; 3-bromo-N, N'-dicarbazolyl-4,4'-biphenyl (1.0 mmol), 2-phenyl-N-4-phenyl-benzo (0.1 mmol), tetrakis (triphenylphosphine)palladium (Pd (PPh 3) 4) (0.05 mmol), potassium carbonate (K 2 CO 3) (2M, 10 ml), toluene (50 ml), ethanol (20 ml), and the aircontained in the solution was driven off by the addition of nitrogen. The resulting solution was heated under reflux in a nitrogenatmosphere for 24 hours. The reaction solution was cooled to room temperature, extracted three times with dichloromethane,washed three times with water, Dried over anhydrous magnesium sulfate, filtered and evaporated to dryness under reducedpressure to give the crude product which was sublimed directly with a sublimation machine to give a white solid product in 75%yield.
  • 14
  • [ 867044-33-5 ]
  • 2'-chloro-4,4"-di(1-isoquinolyl)-1,1':4',1"-terphenyl [ No CAS ]
  • 4-(2-phenyl-1 H-benzimidazol-1-yl)-4"-(1-isoquinolyl)-5'-[4-(1-isoquinolyl)phenyl]-1, 1':2',1"-terphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.4% With palladium diacetate; potassium carbonate; XPhos; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere; Under an argon stream,2'-Chloro-4,4 '' - di (1-isoquinolyl) -1,1 ': 4', 1 '' - terphenyl490 mg (0.944 mmol),356 mg (1.13 mmol) of 4- (2-phenyl-1 H-benzimidazol-1-yl) phenylboronic acid,10.6 mg (0.0472 mmol) of palladium acetate,45.0 mg (0.0944 mmol) of 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl,And 4.53 mL (4.53 mmol) of a 1 M potassium carbonate aqueous solution,Was dissolved in 15 mL of dioxane,And the mixture was heated and stirred at 100 C. for 4 hours.After cooling to room temperature,150 mL of pure water was added, and the mixture was separated and extracted with chloroform. After distilling off the solvent under reduced pressure, the obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain the objective 4- (2-phenyl-1H-benzimidazol-1-yl) -4 " (1-isoquinolyl) -5 '- [4- (1-isoquinolyl) phenyl] -1,1': 2 ', 1 "- terphenyl(Yield 531 mg, yield 74.7%).
  • 15
  • [ 867044-33-5 ]
  • 2'-chloro-4,4"-di(2-quinolyl)-1,1':4',1"-terphenyl [ No CAS ]
  • 4-(2-phenyl-1H-benzoimidazol-1-yl)-4"-(2-quinolyl)-5'-[4-(2-quinolyl)phenyl]-1,1':2',1"-terphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.2% With palladium diacetate; potassium carbonate; XPhos; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere; Under an argon stream,832 mg (1.60 mmol) of 2'-chloro-4,4 "-di (2-quinolyl) -1,1 ': 4', 1"604 mg (1.92 mmol) of 4- (2-phenyl-1 H-benzimidazol-1-yl) phenylboronic acid,18.0 mg (0.0802 mmol) of palladium acetate,76.4 mg (0.160 mmol) of 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl,And 7.69 mL (7.69 mmol) of 1 M potassium carbonate aqueous solution were dissolved in 25 mL of dioxane and heated and stirred at 100 C. for 4 hours.After cooling to room temperature, 200 mL of pure water was added and the mixture was filtered, and the obtained solid was washed with pure water, methanol, and hexane. The resulting crude product was dried and then recrystallized twice using chlorobenzene as a solvent to obtain the objective(2-quinolyl) -5 '- [4- (2-quinolyl) phenyl] -1,1': 2 ', 1 '' - terphenylOf light yellow solid (yield 763 mg, yield 63.2%).
  • 16
  • [ 867044-33-5 ]
  • 2'-chloro-4,4"-di(5-methylpyridin-2-yl)-1,1': 4',1"-terphenyl [ No CAS ]
  • 4-(5-methylpyridin-2-yl)-4"-(2-phenyl-1H-benzoimidazol-1-yl)-4'-[4-(5-methylpyridin-2-yl)phenyl]-1,1':2',1"-terphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
61.6% With palladium diacetate; potassium carbonate; XPhos; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere; 600 mg (1.34 mmol) of 2'-chloro-4,4 "-di (5-methylpyridin-2-yl) -1,1 ': 4', 1" - terphenyl,506 mg (1.61 mmol) of 4- (2-phenyl-1 H-benzimidazol-1-yl) phenylboronic acid,15.0 mg (0.0670 mmol) of palladium acetate,63.9 mg (0.134 mmol) of 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl,And 6.43 mL (6.43 mmol) of 1 M potassium carbonate aqueous solution were dissolved in 21 mL of dioxane and heated and stirred at 100 C. for 4 hours. After cooling to room temperature, 200 mL of pure water was added and the mixture was separated and extracted.After distilling off the solvent under reduced pressure, the obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform: ethyl acetate = 10: 1)The objective 4- (5-methylpyridin-2-yl) -4 "- (2-phenyl- 1 H-benzimidazol- 1 - yl) -4 '- [4- Phenyl] -1, 1 ': 2', 1 "-terphenyl as a white solid(Yield 561 mg, yield 61.6%).
  • 17
  • [ 867044-33-5 ]
  • [ 390357-42-3 ]
  • 2,8-bis(4-(2-phenyl-1H-benzo[d]imidazol-1-yl)phenyl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 110℃; for 24h; To a mixed solution of dioxane (80 ml) and water (10 ml)2,8-dibromo-6,12-dihydro-5,11-methanodibenzo [b, f] [1,5] diazocine(1.00 g, 2.63 mmol),(4- (2-phenyl-1H-benzo [d] imidazol-1-yl) phenyl) boronic acid(2.07 g, 6.58 mmol),tetrakis (triphenylphosphine) palladium (0)(0.15 g, 0.132 mmol), (1.45 g, 10.52 mmol) was added thereto and refluxed for 24 hours.After cooling the reaction solution,The solvent was removed by decompression.After extraction with dichloromathane, the organic layer was separated and dried with sodium sulfate (anhydrous)The solvent was removed by decompression.Hexane: Ethyl Acetate = 2: 1 to obtain a solid product (1.26 g, 63%).
  • 18
  • [ 867044-33-5 ]
  • 5-(10-bromoanthracen-9-yl)-2-phenylpyridine [ No CAS ]
  • C44H29N3 [ No CAS ]
  • 19
  • [ 867044-33-5 ]
  • [ 15810-15-8 ]
  • 4-(1-(3,5-dicyanophenyl)-1H-benzo[d]imidazol-2-yl)benzeneboronic acid [ No CAS ]
  • C54H32N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;Inert atmosphere; Reflux; In a three-necked bottle, put 9,10-dibromophenanthrene, 4-(1-(3,5-dicyanophenyl)-1H-benzo[d]imidazolyl)benzeneboronic acid,4-(2-phenyl-1H-benzo[d]imidazolyl)benzeneboronic acid, solvent 50 ml, equipped with a mechanical stir bar,Nitrogen gas was introduced for 15 min, and the catalyst PdCl2 (dppf) was added to 0.25 mol% to 3 mol% under a nitrogen atmosphere, and the 2 M alkali solution was 0.018 mol, and the mixture was heated under reflux for 5-7 hours.After the reaction, suction filtration, toluene washing, and ethanol washing.After recrystallization from xylene, a powder having a purity of 99% or more was obtained in a yield of 76%.
  • 20
  • [ 867044-33-5 ]
  • C26H14N6O2 [ No CAS ]
  • C52H32N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.4% With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; In ethanol; water; toluene; at 100℃; for 12h;Inert atmosphere; Nitrogen protection, intermediate M1 (36.5 g, 100 mmol) and 1-(4-boronophenyl)-2-phenyl-1H-benzimidazole (2.30 eq),Potassium carbonate (5 eq), Pd2 (dba) 3 (2% eq) toluene 1000 mL + ethanol 500 ml + water 300 ml, stirring was started, heated to 100 C reflux, reaction 12 h,The reaction was washed with water, the organic phase was dried, silica gel column, and concentrated, washed with boiling petroleum ether to afford Intermediate M2 (31.2g, yield 85.4%).
  • 21
  • [ 867044-33-5 ]
  • C22H13Cl [ No CAS ]
  • C41H26N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 90℃; for 20h;Inert atmosphere; Under an argon atmosphere, intermediate 1(1.00 g, 3.20 mmol),[4- (2-phenylbenzimidazol-1-yl)Phenyl] boronic acid (1.11 g, 3.52 mmol), palladium acetate (0.029 g, 0.128 mmol),XPhos (0.122 g, 0.256 mmol),Cesium carbonate (2.08 g, 6.39 mmol),1,4-Dioxane (13 mL)Was stirred at 90 C. for 20 hours. After completion of the reaction,After cooling to room temperature, the solvent was concentrated under reduced pressure.The crude product was purified by silica gel column chromatography,Compound 2 was obtained (1.05 g, yield 60%).
  • 22
  • [ 867044-33-5 ]
  • [ 26885-42-7 ]
  • C35H22N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 90℃; for 8h;Inert atmosphere; Under an argon atmosphere, 2-bromofluoranthene (5.00 g, 17.8 mmol),[4- (2-phenylbenzimidazol-1-yl) phenyl] boronic acid (6.16 g, 19.6 mmol),Palladium acetate (0.160 g, 0.712 mmol),XPhos (2-dicyclohexylphosphino-2 ', 4', 6'-triisopropyl-1,1'-biphenyl)(0.678 g, 1.42 mmol),Cesium carbonate (11.6 g, 35.6 mmol),A mixture of 1,4-dioxane (70 mL) was stirred at 90 C. for 8 h. After completion of the reaction, the reaction mixture was cooled to room temperature, and the solvent was concentrated under reduced pressure.The crude product was purified by silica gel column chromatography,Compound 1 was obtained (5.95 g, yield 71%).
  • 23
  • [ 867044-33-5 ]
  • [ 1564-64-3 ]
  • [ 944801-79-0 ]
YieldReaction ConditionsOperation in experiment
93.7% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 8h;Inert atmosphere; Reflux; Under nitrogen protection,With mechanical stirring,9-bromoindole (25.9 g, 10 mmol),<strong>[867044-33-5][4-(2-phenyl-1H-benzimidazol-1-yl)phenyl]boronic acid</strong> (1.1 eq.),Potassium carbonate 2eq,Pd(Pph3)4 (1%),Toluene 500ml + ethanol 100ml + 100ml water,Turn on the agitation,Heated to reflux,Reaction 8h.Organic phase silica gel column chromatography,concentrate,Recrystallization from toluene gave yellow powder M1 (4.2 g, 93.7%).
  • 24
  • [ 867044-33-5 ]
  • C53H34N4 [ No CAS ]
  • 25
  • [ 867044-33-5 ]
  • [ 944801-80-3 ]
  • 26
  • [ 867044-33-5 ]
  • C28H15BBrN3O2 [ No CAS ]
  • C47H28BN5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.7% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 6h;Inert atmosphere; Reflux; In a 2000 ml four-necked flask, intermediate M11 (51.6 g, 0.1 mol) was added.A10-1 (34.6 g, 0.11 mol), toluene (516 ml),Ethanol (130 ml), water (100 ml), potassium carbonate (27.2 g, 0.2 mol),Tetrakistriphenylphosphine palladium (1.2 g), three times with nitrogen, protected with nitrogen and stirred at reflux for 6 h. Stop the reaction and add ethyl acetate and water to the reaction solution. The aqueous phase was washed twice with ethyl acetate (500 mL). The combined organic phases were washed once with saturated brine (500 ml). The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was taken up in vacuo, dissolved in dichloromethane and purified using silica gel column chromatography. The eluent is ethyl acetate: petroleum ether = 1:5, 49.2 g of a white powder solid were obtained in a yield of 66.7%.
  • 27
  • [ 760212-58-6 ]
  • [ 121-43-7 ]
  • [ 7732-18-5 ]
  • [ 867044-33-5 ]
YieldReaction ConditionsOperation in experiment
60% 7 g of 1-(4-bromophenyl)-2-phenylbenzimidazole (0.02 mol) was added to 150 ml of THF, and the temperature was lowered to -78 C, and 12 ml (2.5 M/L, 0.03 mol) was added dropwise at -78 C. n-BuLi, keep warm for 30 minutes, add 4.26g (0.041mol) of trimethyl borate, after 2 hours of reaction, the reaction is completed, add 50ml of water to the reaction solution, stir for 20 minutes, add hydrochloric acid to adjust the pH to acidity, stir 30 The reaction solution was extracted three times with ethyl acetate. The organic layer was combined and washed with water, and then the organic phase was separated and evaporated to dryness. The solid was digested twice with petroleum ether and filtered to give 2 g of white solid intermediate A, yield 60%.
  • 28
  • [ 867044-33-5 ]
  • [ 186517-01-1 ]
  • C52H34N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux; 6.28 g (0.02 mol) of intermediate G25-1, 2.66 g (0.01 mol) of 2,6-dibromofluorene,4.15 g (0.03 mol) of potassium carbonate, 50 ml of toluene, 30 ml of ethanol and 30 ml of water were mixed.The reaction was carried out by adding 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium under a nitrogen atmosphere.The temperature was raised to reflux, the spot plate was monitored until the reaction was completed, the reaction was terminated, the reaction solution was spun dry, 100 ml of dichloromethane was added, and the solution was completely dissolved and passed through a silica gel column. The filtrate was added with 100 ml of water, washed with water, and the organic phase was separated and dried. It was boiled twice with ethanol and filtered to obtain 4.3 g of a white solid compound G25-2 in a yield of 60%.
  • 29
  • [ 867044-33-5 ]
  • [ 186517-01-1 ]
  • C52H32Br2N4 [ No CAS ]
  • 30
  • [ 867044-33-5 ]
  • [ 121848-75-7 ]
  • C66H42N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.14% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 5h;Inert atmosphere; Reflux; In a 1000 ml three-necked flask with mechanical stirring, Ar gas protection, adding 10,10'-dibromo-9,9'-bifluorene (BA) 7.68 g (molecular weight 512, 0.015 mol), <strong>[867044-33-5]4-(2-phenylbenzimidazol-1-yl)benzeneboronic acid</strong> (BM1) 11.1g (molecular weight 314, 0.035mol), catalyst Pd (PPh3)4The dosage was 1.8 g (molecular weight 1154, 0.001556 mol), sodium carbonate aqueous solution 120 ml (2 M), toluene 300 ml, and ethanol 150 ml.The mixture was stirred and refluxed for 5 hours, and the reaction was monitored by TLC.The product was isolated by column chromatography eluting with 1:1 ethyl acetate: petroleum ether afforded 10.12 g of a white solid.The product had a molecular weight of 764, a molecular weight of 890, a purity of 99.57%, and a yield of 87.14%.
  • 31
  • [ 867044-33-5 ]
  • C37H24BrN [ No CAS ]
  • C56H37N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.8% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 15h;Inert atmosphere; Reflux; Step 2: Bring nitrogen into a 250 mL three-necked flask, add 0.01 mol of intermediate C8, 0.015 mol of raw material B7, dissolve in a mixed solvent (90 mL of toluene, 45 mL of ethanol), then add 0.03 mol of Na2CO3 aqueous solution (2M), and stir under nitrogen After 1 hour, 0.0001 mol of Pd(PPh3)4 was added, and the mixture was heated under reflux for 15 hours. The sample was spotted and the reaction was complete. It was left to cool, filtered, and the filtrate was spin-evaporated and passed through a silica gel column to obtain the target product. The purity by HPLC was 96.8%, and the yield was 74.8%.
  • 32
  • [ 867044-33-5 ]
  • C57H35BrN2 [ No CAS ]
  • C64H41N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 65℃; for 18h; 1,3-phenylenediboronic acid (5.6g, 0.034mol / alfa aesar) on intermediate A (5.0g, 0.014mol),150 ml of THF was added to Pd (pph3) 3 (0.8 g, 0.0007 mol / p & h tech) and potassium carbonate (3.9 g, 0.0328 mol / sigma aldrich) and reacted by stirring at 65 C. for 18 hours.After completion of the reaction, the mixture was cooled and column separated after H20: MC separation.(n-Hexane: MC) afforded 4.6 g (75% yield) of intermediate 1-1.
  • 33
  • [ 867044-33-5 ]
  • C25H16BrN [ No CAS ]
  • C44H29N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux; Under nitrogen protection,In a 1000 ml three-necked flask, 8.35 g (20.36 mmol, 1 eq) of Compound 3 was added,6.67 g (21.38 mmol, 1.05 eq) of compound 1,8.43g (61.09mmol, 3eq) potassium carbonate was put into the reaction flask,Then add 90mL toluene, 45mL ethanol,45mL water, start stirring,Nitrogen was bubbled for 20 min, and then 0.235 g (0.204 mmol, 0.01 eq) of tetratriphenylphosphonium palladium was added.The reaction was heated at reflux overnight. The plate was spotted until the intermediate 1 was basically complete.The reaction was stopped. The aqueous phase was separated and the temperature was reduced to 300 ml, and the organic phases were combined and dried.Spin dry, dissolve the solid in DCM and stir the silica gel,By column to give the pure product 8.54 g, yield 70%
  • 34
  • [ 867044-33-5 ]
  • C43H35BN2O2 [ No CAS ]
  • 35
  • [ 867044-33-5 ]
  • C52H33N5 [ No CAS ]
 

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