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[ CAS No. 4373-72-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 4373-72-2
Chemical Structure| 4373-72-2
Chemical Structure| 4373-72-2
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Product Details of [ 4373-72-2 ]

CAS No. :4373-72-2 MDL No. :MFCD16250222
Formula : C11H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :LCTYNEHIFPECNL-UHFFFAOYSA-N
M.W : 234.09 Pubchem ID :13150402
Synonyms :

Calculated chemistry of [ 4373-72-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.37
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 3.78
Log Po/w (WLOGP) : 3.51
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 3.7
Consensus Log Po/w : 3.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.29
Solubility : 0.012 mg/ml ; 0.0000513 mol/l
Class : Moderately soluble
Log S (Ali) : -3.74
Solubility : 0.0422 mg/ml ; 0.00018 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.4
Solubility : 0.00093 mg/ml ; 0.00000397 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.55

Safety of [ 4373-72-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4373-72-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4373-72-2 ]

[ 4373-72-2 ] Synthesis Path-Downstream   1~31

  • 1
  • m-pyridin-4-ylbromobenzene [ No CAS ]
  • [ 101681-34-9 ]
  • [ 39795-60-3 ]
YieldReaction ConditionsOperation in experiment
1% EXAMPLE II Example I was essentially repeated except that the bromination was conducted in the absence of a solvent. The process resulted in a 31percent yield of 4-(4-bromophenyl)pyridine, a 31percent yield of 4-(3-bromophenyl)pyridine, and a 1percent yield of 4-(2-bromophenyl)pyridine.
  • 2
  • [ 4373-72-2 ]
  • [ 73183-34-3 ]
  • [ 1009033-83-3 ]
YieldReaction ConditionsOperation in experiment
93% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere;
93% With potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In 1,4-dioxane at 85℃; for 24h; Inert atmosphere; 3.2 Pyridine boronic acid ester Under a nitrogen atmosphere, to a 250ml three-necked flask was added 3- (4-pyridinyl) yl bromobenzene (11.1g, 47.5mmol), United pinacolato ester (13.3 g , 52.2mmol, TCI), potassium acetate (14.0g, 142mmol), 1,1'- bis (diphenylphosphino) ferrocene palladium dichloride (1.94 g, 2.38mmol) and 1,4-dioxane ring (150ml), and 1,4-dioxane (150ml), was heated at 85 and stirred for 24h.After completion of the reaction was allowed to cool, the reaction solution was extracted with ethyl acetate, washed with saturated brine three times, the resulting organic layer is dried over anhydrous magnesium sulfate.Filtration, the resulting filtrate under reduced pressure to remove the solvent.Separated by column chromatography, the mobile phase was chloroform / ethyl acetate = 2: 1.After the spin-dry vacuum dried to give a white powder 14.6g, yield 93%.
82% With potassium acetate In 1,4-dioxane at 80℃; for 24h; 4 1.0 g of compound 17 (4.27 mmol), 1.2 g of bis(pinacolato) diboron (4.7 mmol), 174 mg of PdCl2(dppf) (0.21 mmol), 1.3 g of potassium acetate (12.8 mmol) and 50 mL of dry dioxane were added to a 250 mL two-necked flask and heated to 80° C. with stirring for 24 hours. After the temperature was lowered to room temperature, the resulting solution was filtered with Celite545 and extracted using ethyl acetate and saturated saline. After removal of water of the extracted solution by adding dry magnesium sulfate, filtered and concentrated by reducing the pressure, the concentrated results were purified using column chromatography (silicon dioxide, trichloromethane/ethyl acetate=2/1). Thus, 984 mg of light yellow solid product (compound 18) was obtained, with a yield of 82%.
  • 3
  • [ 591-18-4 ]
  • [ 181219-01-2 ]
  • [ 4373-72-2 ]
YieldReaction ConditionsOperation in experiment
54% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Inert atmosphere; Reflux;
54% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 24h; Inert atmosphere; 3.1 Preparation of pyridyl bromobenzene Under a nitrogen atmosphere, to a 250ml three-necked flask was added 4-pyridine boronic acid ester (18.1g, 88.4mmol, Aldrich), 3- iodo-1-bromobenzene (25g, 88.4mmol , Aldrich), tetrakis (triphenylphosphine) palladium (2.04g, 1.77mmol, TCI), 2M aqueous potassium carbonate solution (100ml), toluene (150ml) and ethanol (50ml), was heated at 85 and stirred for 24h.After completion of the reaction was allowed to cool, the reaction solution was extracted with toluene, washed with saturated brine three times, the resulting organic layer was dried over anhydrous magnesium sulfate.Filtration, the resulting filtrate was removed under reduced pressure to remove the solvent.Separated by column chromatography, the mobile phase n-hexane / ethyl acetate = 3: 1.After the spin dry and dried under vacuum to give a colorless oily product, 3- (4-pyridyl) group bromobenzene 11.1g, yield 54%.
1.13 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 6h; Inert atmosphere; 2.1 (i) Synthesis of XX-6 In a iOO-mL reaction container, 2.09 g (7.4 mmol) of i -bromo-3-iodobenzene and i .Oi g (4.9 mmol) of 4-pyridylboronic acid pinacol ester were mixed in a solvent mixture of toluene (6 mE), ethanol (3 mE), and distilled water (6 mE), and dissolved oxygen was removed bynitrogen. Subsequently, i 85 mg (0. i 6 mmol) of Pd(PPh3)4and 6 mE of an aqueous solution of i M sodium carbonatewere added to the mixture under a nitrogen atmosphere, followed by heating at 80° C. for 6 hours for reaction.The reaction solution was cooled to room temperature,concentrated under reduced pressure, and subjected to silicagel chromatography (mobile phase: ethyl acetate) for isolation and purification to obtain XX-6 (i.i3 g).
  • 4
  • [ 1120-87-2 ]
  • [ 591-18-4 ]
  • [ 4373-72-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-bromopyridin With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.416667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; for 2h; Stage #3: 1-Bromo-3-iodobenzene In tetrahydrofuran; diethyl ether; hexane at 20℃; for 92h; 25 Reference Example 25; Preparation method of 4-(3-bromophenyl)pyridine; In an amount of 1.0 g of 4-bromopyridine hydrochloride was added with 5.2 ml of 1 N aqueous sodium hydroxide, and extracted three times with 10 ml of methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated at 0°C under reduced pressure to obtain 4-bromopyridine. Without purification, this compound was dissolved in 23 ml of tetrahydrofuran under argon atmosphere, added with 4 ml of a 1.58 M solution of n-butyllithium in hexane at -78°C, stirred for 25 minutes, then added with 5.2 ml of a 1 M solution of zinc chloride in diethyl ether, then warmed to room temperature over 2 hours or more, added with 60 mg of tetrakis(triphenylphosphine)palladium dissolved in 7.5 ml of tetrahydrofuran and 0.68 ml of 1-bromo-3-iodobenzene, and further stirred for 92 hours. The reaction mixture was concentrated under reduced pressure, and then added with 100 ml of ethyl acetate, and the organic layer was successively washed with 45 ml of 10% aqueous ammonia, and 50 ml of saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate (4:1 to 3:1)) to obtain 127 mg of the title compound. Physicochemical properties of this compound (1) Molecular formula: C11H8BrN (2) Mass spectrum (FAB): m/z 234 (M+H)+ (3) 1H NMR spectrum (300 MHz, CDCl3) δ (ppm): 7.36 (t, C6H4), 7.46 (d, pyridine), 7.56 (m, C6H4), 7.77 (s, C6H4), 8.68 (d, pyridine).
  • 5
  • [ 591-18-4 ]
  • [ 1692-15-5 ]
  • [ 4373-72-2 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In ethanol; toluene for 24h; Reflux; Inert atmosphere; 4 5.0 g of compound 15 (40.6 mmol), 11.5 g of compound 16 (40.6 mmol), 2.3 g of Pd(PPh3)4 (2.0 mmol), 43 mL of K2CO3 (2M), 100 mL of toluene and 50 mL of ethanol were added to a 500 mL two-necked flask and heated to reflux for 24 hours under nitrogen gas. After returning to room temperature, the resulting solution was extracted using 20 mL of dichloromethane for several times. The organic layer was then washed with saturated saline and collected. After removal of water of the collected solution by adding dry magnesium sulfate, filtered and concentrated by reducing the pressure, the concentrated results were purified using column chromatography (silicon dioxide, trichloromethane/ethyl acetate=3/1). Thus, 7.5 g of colorless liquid product (compound 17) was obtained, with a yield of 79%.
  • 6
  • [ 4373-72-2 ]
  • [ 1268613-33-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 24 h / 80 °C 2: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 48 h / Reflux
  • 7
  • [ 110-86-1 ]
  • [ 585-76-2 ]
  • m-pyridin-4-ylbromobenzene [ No CAS ]
  • [ 4422-32-6 ]
  • [ 4373-60-8 ]
  • 8
  • [ 4373-72-2 ]
  • [ 542-91-6 ]
  • [ 1846554-45-7 ]
YieldReaction ConditionsOperation in experiment
2.1 g Stage #1: m-pyridin-4-ylbromobenzene With tris(pentafluorophenyl)borate In toluene for 0.0833333h; Inert atmosphere; Stage #2: H2SiEt2 In toluene at 110℃; for 24h; Inert atmosphere; chemoselective reaction;
  • 9
  • [ 4373-72-2 ]
  • [ 1827620-76-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tris(pentafluorophenyl)borate / toluene / 0.08 h / Inert atmosphere 1.2: 24 h / 110 °C / Inert atmosphere 2.1: triethylamine; dmap / dichloromethane / 12 h / 0 - 23 °C / Inert atmosphere
  • 10
  • [ 4373-72-2 ]
  • [ 775-12-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With tris(pentafluorophenyl)borate In (2)H8-toluene at 125℃; for 36h; Inert atmosphere; chemoselective reaction;
  • 11
  • [ 4373-72-2 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
50 %Spectr. With tris(pentafluorophenyl)borate In (2)H8-toluene at 120℃; for 12h; Inert atmosphere; chemoselective reaction;
  • 12
  • [ 4373-72-2 ]
  • [ 79-22-1 ]
  • [ 1884713-14-7 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate In methanol at -78℃; Inert atmosphere;
  • 13
  • [ 4373-72-2 ]
  • [ 1884712-85-9 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / -78 °C / Inert atmosphere 2: <i>tert</i>-butyl alcohol; copper(l) chloride; potassium <i>tert</i>-butylate; ((2R,4R)-(-)-2,4-bis(diphenylphosphine)pentane) / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
  • 14
  • [ 4373-72-2 ]
  • [ 1787242-97-0 ]
  • [ 1787242-98-1 ]
YieldReaction ConditionsOperation in experiment
51 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 6.5h; Inert atmosphere; 2.2 In a 50-mE reaction container, i i3mg (0.48 mmol) of XX-6 prepared in (i) and 80 mg (0.22mmol) of XX-7 were mixed in a solvent mixture oftoluene (6mE) and ethanol (3 mE), wherein XX-7 is a compound synthesized using 3,4-dimethylthiophene as a starting material inaccordance with the synthetic method described in Mci, Jianguo; Heston, Natha C.; Vasilyeva, Svetlana V., et al. Macromolecules, vol. 42, No. 5, pp. i482-i487, and dissolved oxy20 gen was removed by nitrogen. Subsequently, 24 mg (0.02mmol) of Pd(PPh3)4 and 6 mE of an aqueous solution of i Msodium carbonate were added to the mixture under a nitrogenatmosphere, followed by heating at iOO° C. for 6.5 hours forreaction.The reaction solution was cooled to room temperature,concentrated under reduced pressure, and subjected to silicagel chromatography (mobile phase: ethyl acetate/ethanol=5/i) for isolation and purification to obtain XX-8 (Si mg).
  • 15
  • [ 4373-72-2 ]
  • [ 955023-57-1 ]
  • [ 1841130-16-2 ]
YieldReaction ConditionsOperation in experiment
40% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene Inert atmosphere; Reflux; 24 Synthesis of Compound 5-24 (HSB-06-010) Pitching 100 mL flask was charged with intermediate (3) 0.5 g (0.943 mmol), 4 - (3 - bromophenyl) pyridine (4 - (3-bromophenyl) pyridine), 0.184 g (0.786 mmol) and Pd (PPh3) 4 46 was introduced into the mg (0.037 mmol) was dissolved in Toluene 6 mL EtOH and 3 mL under a nitrogen atmosphere, was added a 2M K2CO3 solution 1 mL was stirred under reflux. After completion of the reaction, the reaction was cooled to room temperature and added to 5 mL H2O. Drying the mixture and then extracted twice with MC 10 mL extract with Na2SO4, filtered and concentrated under a reduced pressure. Purification of the resulting compound by silica gel column chromatography to 0.21 g compound (5-24, HSB-06-010) of a white solid was obtained (yield: 40%).
  • 16
  • [ 4373-72-2 ]
  • [ 400607-46-7 ]
  • [ 1379518-33-8 ]
YieldReaction ConditionsOperation in experiment
1.54 g With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; isopropyl alcohol for 10h; Inert atmosphere; Reflux; 10 4-(3-(10-(naphthalen-1-yl)anthracen-9-yl)phenyl)pyridine synthesis commercially available (10-(naphthalen-1-yl)anthracen-9-yl)boronic acid 2.78g, 4-(3-bromophenyl)pyridine 2.25g, tetrakis(triphenylphosphine)palladium(0) 0.28g, potassium phosphate 3.39g, pseudocumene 20 ml, isopropyl alcohol 4 ml, and 1 ml water placed in a flask, under nitrogen atmosphere, this mixture was stirred for 10 hours at reflux temperature. The reaction liquid to room temperature by cooling, and toluene liquid water addition. Solvent under a reduced pressure, a solid obtained by refining alumina column chromatography (soln.: toluene). A reduced pressure of solvent elution liquid, by recrystallization from toluene, 4-(3-(10-(naphthalen-1-yl)anthracen-9-yl)phenyl)pyridine (1.54g) is obtained.
  • 17
  • [ 4373-72-2 ]
  • [ 1821521-84-9 ]
  • [ 1821521-85-0 ]
YieldReaction ConditionsOperation in experiment
25 g With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene; <i>tert</i>-butyl alcohol for 6h; Inert atmosphere; Reflux; 8 [Synthesis Example 8] (Synthesis of 4,4 '- ((2-chloro anthracene-9,10-diyl) bis (3,1-phenylene)) dipyridine) 2,2 '- (2-chloro anthracene -9,10-diyl) bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (57.5 g ) synthesized by the methodof Synthesis Example 7, and 4- (3-bromophenyl) pyridine (61.0 g), tetrakis(triphenylphosphine) palladium (0) (7.16 g), tripotassium phosphate (105 g),toluene (250 ml), t-butanol ( 50 ml), water (10ml) were placed in a flask, andunder a nitrogen atmosphere, it was stirred for 6 hours at reflux temperature.The reaction mixture was cooled, filtered through Celite, and the filtrate wasconcentrated. The concentrate was purified by silica gel column chromatography(ethyl acetate), followed by washing with methanol, and dried in vacuo toobtain 4,4 '- ((2-chloro anthracene -9,10-diyl) bis (3,1-phenylene ))dipyridine (25.0g).
  • 18
  • [ 4373-72-2 ]
  • [ 542-91-6 ]
  • [ 2002466-32-0 ]
YieldReaction ConditionsOperation in experiment
With chlorobis(cyclooctene)-iridium(I) dimer In neat (no solvent) at 55℃; for 6h;
  • 19
  • [ 4373-72-2 ]
  • [ 1351777-95-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
1.1 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 13h; Inert atmosphere; Reflux; Synthesis of 9-(naphthalen-1-yl)-2,7-bis(3-(pyridin-4-yl)phenyl)-9H-carbazole Obtained as described above 9-(naphthalen-1-yl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (3.5g), to a flask containing 4-(3-bromophenyl)pyridine (3.3g), sodium carbonate (2.7g) and Pd(PPh3)4 (0.5g), toluene (30ml), ethanol (10ml) and water (10ml) were mixed, under an argon atmosphere this mixture was stirred for 13 hours at reflux temperature. The reaction solution was cooled to room temperature, it was subjected to water was added rinsing operation. Purification by organic substances to remove salts by water washing operation active alumina column chromatography (toluene / ethyl acetate = 1/4 (volume ratio)), and finally, the compound represented by formula (1-1-856) We 9 were obtained (naphthalen-1-yl) -2,7-bis (3- (pyridin-4-yl) phenyl)-9H-carbazole (1.1 g).
1.1 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 13h; Inert atmosphere; Reflux; synthesis of 9-(naphthalen-1-yl)-2,7-bis(3-(pyridin-4-yl)phenyl)-9H-carbazole Obtained as described above 9-(naphthalen-1-yl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (3.5 g), 4-(3-bromophenyl)pyridine (3.3g), sodium carbonate (2.7g) and Pd (PPh3) 4 (0.5g) to the flask containing, under an argon atmosphere, toluene (30 ml), ethanol (10ml) and water (10ml), it was placed, and the mixture was stirred for 13 hours at reflux temperature. The reaction mixture was cooled to room temperature, the water was added to washing. Removing the salt by washing operation organics activated alumina column chromatography (toluene / ethyl acetate = 1/4 (volume ratio)) in purified, finally, it is a compound represented by the formula (1-1-856) 9-(naphthalen-1-yl)-2,7-bis(3-(pyridin-4-yl)phenyl)-9H-carbazole (1.1 g) was obtained
  • 20
  • [ 4373-72-2 ]
  • [ 1379746-84-5 ]
  • [ 1379747-00-8 ]
YieldReaction ConditionsOperation in experiment
0.1 g With potassium phosphate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine for 3h; Reflux; Synthesis examples of the compound represented by the formula (1-455) 9- (naphthalen-2-yl) -7-phenyl-5 (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-benzo [c] carbazole (1 .4g), 4- (3- bromophenyl) pyridine (0.7 g), bis (dibenzylideneacetone) palladium (0) (0.2 g), tricyclohexylphosphine (0.2 g), tripotassium phosphate (K3PO4 ) (4.1g) and 1,2,4-trimethyl benzene (pseudo cumene) (was a flask containing 9ml) was stirred for 3 hours at reflux temperature. The reaction mixture was added was cooled to room temperature water was collected precipitated solid by suction filtration. The obtained solid was washed with water then methanol, amino-modified silica gel (NH DM1020: manufactured by Fuji Silysia) column chromatography was purified (eluent toluene / ethyl acetate mixed solvent). At this time, gradually increasing the ratio of ethyl acetate in developing solution to elute the desired product. The solvent was evaporated under reduced pressure, the resulting solid was heated and dissolved in ethyl acetate, row reprecipitation by addition of heptaneNot a compound represented by the formula (1-455), 9- (naphthalen-2-yl) -7-phenyl-5- (3- (pyridin-4-yl) phenyl)-7H-benzo [c ] were obtained carbazole (0.1g).
  • 21
  • [ 4373-72-2 ]
  • [ 1310450-34-0 ]
  • [ 1310450-36-2 ]
YieldReaction ConditionsOperation in experiment
3.5 g With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine at 160℃; for 12h; Inert atmosphere; Synthesis examples of the compound represented by the formula (1-744) The Pseudo cumene (1,2,4-trimethylbenzene) (50 ml), 7- phenyl -7H- benzo [c] carbazole-5,9-diboronic acid ester (4.9 g) and 4- (3-bromophenyl) pyridineTo a solution was added (4.6 g), under a nitrogen atmosphere, palladium catalyst (Pd (PPh3) 4) of triphenylphosphine (0.5 g) and stirring tripotassium phosphate and (K3PO4) (12g) at room temperature added. After stirring 12 hours at 160 ° C., the reaction was cooled to room temperature, ethylenediaminetetraacetic acid (EDTA) solution and ethyl acetate were added, was subjected to washing operations. Was purified by organic substances to remove salts by water washing operation active alumina column chromatography (toluene / ethyl acetate = 4/6 (volume ratio)). Further, recrystallized from toluene, a compound represented by the formula (1-744) 7-phenyl-5,9-bis (3- (pyridin-4-yl) phenyl) 7H-benzo [c] carbazole a (3.5g) was obtained.
  • 22
  • [ 4373-72-2 ]
  • [ 1492917-87-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine / 1,4-dioxane / 24 h / 85 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 24 h / 85 °C / Inert atmosphere
  • 23
  • [ 4373-72-2 ]
  • [ 1492917-90-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine / 1,4-dioxane / 24 h / 85 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 24 h / 85 °C / Inert atmosphere
YieldReaction ConditionsOperation in experiment
With dipotassium peroxodisulfate; silver nitrate; trifluoroacetic acid; In acetonitrile; at 120℃; for 12h;Sealed tube; General procedure: Potassium persulfate (K2S2O8) (2 mmol, 405.6 mg) and the substituted benzyl alcohol (0.25 mmol) was added to the (dried by a heat gun (heat gun)) pressure tube. Silver nitrate (AgNO3) (35 molpercent) is then added to the tube, and then Pyridines (10 mmol), ACN (1 ml) and TFA (25 mmol) were added by syringe. The tube was sealed with Teflon (Teflon) screw cap, and after ultrasonic treatment for five minutes, and then placed in a 120 five days. Heat was applied for 12 hours, and washed with a short plug of silica gel and an abundance of DCM. The purification and separation procedures are the same as described above. In addition, the present invention relates to a process for the cross-coupling reaction of pyridine, Benzyl alcohol and benzylamine were used as substrates to obtain satisfactory yields, and Toluene did not satisfy the reaction conditions, the cross-coupling reaction of various benzyl alcohols with pyridine was carried out at a high yield of 42-89percent.
  • 25
  • [ 4373-72-2 ]
  • [ 1369417-88-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; potassium acetate; potassium carbonate; bis(pinacol)diborane / 12 h / Reflux 1.2: 8 h / Reflux 2.1: N-Bromosuccinimide / chloroform / 18 h / 20 °C
  • 26
  • [ 4373-72-2 ]
  • [ 1369417-66-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; potassium acetate; potassium carbonate; bis(pinacol)diborane / 12 h / Reflux 1.2: 8 h / Reflux 2.1: N-Bromosuccinimide / chloroform / 18 h / 20 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane / 4 h / Reflux 3.2: 4 h / Reflux
  • 27
  • [ 4373-72-2 ]
  • [ 1369417-68-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; potassium acetate; potassium carbonate; bis(pinacol)diborane / 12 h / Reflux 1.2: 8 h / Reflux 2.1: N-Bromosuccinimide / chloroform / 18 h / 20 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane / 5 h / Reflux 3.2: 4 h / Reflux
  • 28
  • [ 4373-72-2 ]
  • [ 1369418-00-7 ]
  • [ 1369417-70-8 ]
YieldReaction ConditionsOperation in experiment
1.4 g With potassium phosphate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In water; <i>tert</i>-butyl alcohol for 3h; Reflux; Synthesis of Compound Represented by Formula (1-27) (10- (6- (pyridin-4-yl) naphthalen-2-yl)Anthracene-9-yl) boronic acid(6.6 g),4- (3-bromophenyl) pyridine (4.4 g), Pd (dba) 2 (0.27 g)A flask containing tricyclohexylphosphine (0.26 g), potassium phosphate (9.9 g), 1,2,4-trimethylbenzene (50 ml), t-butyl alcohol (10 ml) and water (5 ml) And the mixture was heated and stirred at reflux temperature for 3 hours. After the reaction solution was cooled to room temperature, water and toluene were added thereto to separate the layers, and the organic layer was washed with an aqueous EDTA · 4Na solution and then with water. The solvent was distilled off under reduced pressure, and the residue was purified by activated alumina column chromatography (eluent: chlorobenzene / ethyl acetate mixed solvent). At this time, the ratio of ethyl acetate in the developing solution was gradually increased to elute the target product. The residue was purified by activated charcoal column chromatography (eluent: toluene). The solvent was distilled off under reduced pressure, and the residue was recrystallized from chlorobenzene to obtain a compound (1.4 g) represented by the formula (1-27).
  • 29
  • [ 4373-72-2 ]
  • [ 1564-64-3 ]
  • [ 1369417-85-5 ]
YieldReaction ConditionsOperation in experiment
24.6 g Stage #1: 9-Bromoanthracene With potassium acetate; potassium carbonate; bis(pinacol)diborane; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine for 12h; Reflux; Stage #2: m-pyridin-4-ylbromobenzene With tetrakis(triphenylphosphine) palladium(0) In <i>tert</i>-butyl alcohol for 8h; Reflux; Synthesis of 4- (3- (anthracen-9-yl) phenyl) pyridine 9-bromoanthracene (25.0 g),Bispinacolatodiboron (27.0 g), Pd (dba) 2 (2.8 g),Tricyclohexylphosphine (2.7 g), potassium acetate (19.0 g),A flask containing potassium carbonate (14.0 g) and cyclopentyl methyl ether (200 ml)And the mixture was heated and stirred at a reflux temperature for 12 hours. Once cooled to room temperature,4- (3-bromophenyl) pyridine (27.0 g),Pd (PPh3) 4 (3.3 g), t-butyl alcohol (20 ml) and1,2,4-Trimethylbenzene (200 ml) was added, and further at reflux temperatureAnd the mixture was heated and stirred for 8 hours. After cooling the reaction solution to room temperature,The solid precipitated by suction filtration was removed, and an EDTA · 4Na aqueous solution was added to separate the layers.The solvent was distilled off under reduced pressure, and the resulting oil was purified by silica gel column chromatography (eluent: toluene / ethyl acetate mixed solvent)4- (3- (anthracen-9-yl) phenyl) pyridine (24.6 g).At this time, the ratio of ethyl acetate in the developing solution was gradually increased to elute the target product
  • 30
  • [ 110-86-1 ]
  • [ 10269-01-9 ]
  • m-pyridin-4-ylbromobenzene [ No CAS ]
  • [ 4422-32-6 ]
  • [ 4373-60-8 ]
  • 31
  • m-pyridin-4-ylbromobenzene [ No CAS ]
  • [ 2243-47-2 ]
  • N-(3-(pyridin-4-yl)phenyl)[1,1'-biphenyl]-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With palladium diacetate; sodium t-butanolate In toluene at 120℃; for 48h; Inert atmosphere; 2.1 Example 2 (8) according to the present invention can be synthesized by the following method. (1) Add 3-benzidine to a 500 ml three-necked bottle(34g, 200mmol),4-(3-bromophenyl)pyridine (47 g,200 mmol), sodium tert-butoxide (60 g, 600 mmol) was added to 200 g of toluene, and palladium acetate was added under the protection of N2.After reacting at 120 ° C for 48 h, the reaction was completed by TLC.The water (200 ml) was washed three times, decolorized by adding activated carbon, dried and dried to obtain a gray solid, and the product was recrystallized from ethyl acetate.Drying under vacuum gave N-(3-(pyridin-4-yl)phenyl)-[1,1'-biphenyl]-3-amine 55 g, 85% yield.
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