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[ CAS No. 56525-79-2 ] {[proInfo.proName]}

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Chemical Structure| 56525-79-2
Chemical Structure| 56525-79-2
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Product Details of [ 56525-79-2 ]

CAS No. :56525-79-2 MDL No. :MFCD00222619
Formula : C24H17N Boiling Point : -
Linear Structure Formula :- InChI Key :PCMKGEAHIZDRFL-UHFFFAOYSA-N
M.W : 319.40 Pubchem ID :3123295
Synonyms :

Calculated chemistry of [ 56525-79-2 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 25
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 106.68
TPSA : 15.79 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -3.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.15
Log Po/w (XLOGP3) : 6.64
Log Po/w (WLOGP) : 6.66
Log Po/w (MLOGP) : 5.24
Log Po/w (SILICOS-IT) : 6.66
Consensus Log Po/w : 5.67

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.61
Solubility : 0.0000781 mg/ml ; 0.000000245 mol/l
Class : Poorly soluble
Log S (Ali) : -6.77
Solubility : 0.0000539 mg/ml ; 0.000000169 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.97
Solubility : 0.0000000341 mg/ml ; 0.0000000001 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 56525-79-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 56525-79-2 ]

* 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.

  • Upstream synthesis route of [ 56525-79-2 ]
  • Downstream synthetic route of [ 56525-79-2 ]

[ 56525-79-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 6825-20-3 ]
  • [ 98-80-6 ]
  • [ 56525-79-2 ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 16 h; Inert atmosphere It was dissolved in 3,6-dibromo-9H-carbazole(100 g, 308 mmol) in a nitrogen environment in 700 mL tetrahydrofuran(THF), here the phenylboronic acid(45.1 g, 370 mmol) and put tetrakis(triphenylphosphine) palladium (10.7 g, 9.24mmol) was stirred. Into a potassium carbonate (213 g, 1,540 mmol) in a saturated water was heated to reflux at 80 ° C for 16 hours. After the reaction was completed, the reaction solution into water and extracted with DCM then water was removedwith anhydrous MgSO4, filter and was concentrated under reduced pressure. Thus the resulting residue was separated and purified by flash column chromatography to obtain the compound I-23(74.8 g, 76percent).
75% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate In water; tolueneInert atmosphere; Reflux Synthesis of 3,6-diphenyl-9H-carbazole
3,6-Dibromo-9H-carbazole (10.0 g, 30.8 mmol), phenylboronic acid (8.25 g, 67.7 mmol) Pd2(dba)3 (0.564 g, 0.615 mmol), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhOS) (1.011 g, 2.462 mmol), and potassium phosphate hydrate (28.3 g, 123 mmol) were dissolved in the mixture of toluene (350 mL) and water (40 mL) in a three-necked flask.
The mixture was degassed by bubbling nitrogen, then it washeated to reflux overnight.
After completion of the reaction, the mixture partitioned between ethyl acetate and water.
The aqueous layer was washed 3 times with ethyl acetate and the combined organic layers were washed with brine and water.
The crude compound was purified by column chromatography on silica gel, eluted with hexane/DCM 1/1 (v/v) mixture.
The target compound was obtained as a white solid (7.4 g, 75 percent yield).
74% With potassium carbonate In tetrahydrofuranInert atmosphere; Reflux Example 10; a) 3.09 g (9.23 mmol) of 3,6-dibromocarbazole and 2.78 g (22.2 mmol) of phenylboronic acid are stirred in 140 ml of THF under argon. 12.76 g (92.30 mmol) of potassium carbonate in 46 ml of water are added. 0.27 g (0.23 mmol) of palladium tetrakis(triphenylphosphine) are added under argon and the reaction is stirred under reflux over night. At room temperature, a 1 percent aqueous solution of NaCN is added to the medium which is boiled for 20 min. At room temperature, ethyl acetate is added and the organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude material is purified by chromatography over silica gel (cyclohexane/ethyl acetate 4:1 ) to give 2.17 g of a white solid (74percent). 1H NMR (CDCI3, 300 MHz) 8.34 (d, J = 1.8 Hz, 2H), 8.11 (s, 1 H), 7.74- 7.68 (m, 6H), 7.52-7.45 (m, 6H), 7.37-7.32 (m, 2H).
74% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene at 80℃; for 8 h; Inert atmosphere In the nitrogen atmosphere, 3,6-dibromocarbazole (5 g, 15.4 mmol) was added sequentially to the flask, Phenylboronic acid (4.1 g, 33.9 mmol) (Triphenylphosphine) palladium (0.7 g, 0.6 mmol) Toluene (45 ml), 2M sodium carbonate (45 ml), And the mixture was stirred at 80 ° C for 8 hours. After separating the organic phase, Concentrated under reduced pressure in an evaporator. The resulting residue was purified by silica gel column chromatography, 3,6-diphenylcarbazole (3.6 g, yield 74percent) was obtained.
74% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene at 80℃; for 8 h; Inert atmosphere In the nitrogen atmosphere,3,6-dibromocarbazole (5 g, 15.4 mmol) was added sequentially to the flask,Phenylboronic acid (4.1 g, 33.9 mmol)(Triphenylphosphine) palladium (0.7 g, 0.6 mmol)Toluene (45 ml),2M sodium carbonate (45 ml),And stirred at 80 ° C for 8 hours.After separating the organic phase,Concentrated under reduced pressure in an evaporator.The resulting residue was purified by silica gel column chromatography,3,6-diphenylcarbazole (3.6 g, yield 74percent) was obtained.
73% With potassium carbonate In toluene for 10 h; Heating / reflux Preparation of 3,6-diphenylcarbazole Reaction 5As depicted in Reaction 5, 15g (46 mmol) of 3,6-dibromocarbazole, 14g (92 mmol) of phenylboronic acid, K2CO3 (2 mol), Pd(PPh3)4 and toluene were refluxed for 10 hours. The reaction mixture was extracted with methylene chloride. The solvent was removed, and then the residue was purified by column chromatography (eluent: hexane) to give the title compound. Yield: 73percent. MS (El) (Calcd. for C24H17N: 319.14, Found: 319).
68% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; Carbazole (16.72g, 100mmol), NBS (59.4g, 210mmol), BPO (2.42g, 10mmol), methylene chloride (300 ml) at room temperature is injected into the medal and then 2000. When reaction is completed methylene chloride and water, NaHCO 3 extracted using aqueous solution obtained after the organic layer Na 2 SO 4 dried to, for the products and re-crystallized concentrating 23.73g (73percent)obtained. Said product obtained (23.73g, 73.02mmol), phenylboronic acid (19.6g, 160.64mmol), Pd (PPh 3) 4, (8.44g, 7.3mmol), K 2 CO 3 (60.55g, 438.12mmol), THF (320 ml), water (160 ml) in 80 °C agitation return current doesn't have any error frames, turns on the light. When reaction is completed for reducing temperature a high temperature to the normal temperature after methylene chloride and a water extraction of the organic layer obtained after MgSO 4 dried to, for the products and re-crystallized concentrating 15.9g (68percent)obtained
63% With potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 3.5 h; As an example of a material according to the invention, a synthetic method of a compound represented by formula (59) 9-[4-(3, 6-diphenyl-N-carbazolyl)] phenyl- 10-phenylanthracene (hereinafter referred to as DPCzPA) below will be described. [0209][0210] This compound is prepared in accordance with the synthetic method shown below. Note that 9-phenyl-10-(4-bromophenyl) anthracene is prepared in the manner shown in Example 1. [0211]First, a synthetic method of 3,6-dibromocarbazole will be shown below. A mixture of 6.5 g (20.0 mmol) 3,6-dibromocarbazole, 5.0 g (41.0 mmol) of phenylboronic acid, 93 mg (0.40 mmol) of palladium acetate, 6.9 g (5.2 mmol) of potassium carbonate, water (25 mL), 610 mg of tri(ortho-tolyl) phosphine, and dimethoxyethane (50 mL) is heated to reflux at 80 0C for 3.5 three hours. After the reaction, the solution is rinsed with water, aqueous layer is extracted with toluene, and it is rinsed together with the organic layer using saturated salt solution, and thereafter EPO <DP n="67"/>dried with magnesium sulfate. After natural filtration, the filtrate is condensed to obtain 4.1 g of 3,6-di(2-phenyl-phenyl)-carbazoleas a white solid at a yield of 63 percent. A synthetic scheme of 3,6-di(2-phenyl-phenyl)-carbazoleis shown below.
63% With potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 3.5 h; [Step 2] A synthesis method of 3,6-diphenylcarbazole is described.; A synthesis scheme of 3,6-diphenylcarbazole is represented by (a-2). [Show Image] 6.5 g of 3,6-dibromocarbazole (20 mmol), 5.0 g of phenylboron acid (41 mmol), 93mg of palladium(II) acetate (0.40 mmol), 610mg of tri(ortho-tolyl)phosphine (1.9mmol) were put into a 200mL three-necked flask, and then, the inside of the flask was substituted by nitrogen. Into the mixture, 50 ml of ethyleneglycol dimethylether (abbreviation : DME), and 25 mL of a pottassium carbonate water solution (2.0 mol/L) were added. This mixture was refluxed for 3.5 hours at 80 °C. After the reaction, the reaction mixture was washed with water and a water layer was extracted with toluene. The extracted solution and an organic layer were washed with a saturated saline, and dried by magnesium sulphate. The mixture was naturally filtrated. The filtrate was condensed, and 4.1 g of an objective matter, a white powder solid was obtained at the yield 63 percent.
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 17 h; Inert atmosphere A mixture of 3,6-dibromo-9H- carbazole (3.0 g, 9.2 mmol) (Aldrich), phenylboronic acid (3.0 g, 25 mmol) (Aldrich), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.3 g, 0.26 mmol) (Frontier Scientific, Logan, UT) and potassium carbonate (6.5 g, 47 mmol) (Aldrich) in dioxane/water (75 mL/15 mL) (Aldrich) was degassed with bubbling argon (Airgas, San Marcos, CA) for 60 min and heated at about 100 °C on a hot plate with a silicone oil bath for about 16 hours. Upon cooling to room temperature, the whole mixture was mixed with ethyl acetate (Aldrich) and rinsed with brine. Then, the organic mixture was dried over Na2S04 (Aldrich), loaded on silica gel (Grade 135) and purified by flash column using eluents of ethyl acetate/hexanes (10percent to 30percent) (Aldrich). After removal of solvents, a white solid (Compound OSC-3) was obtained (2.1 g, in 63percent yield). Confirmed by 1 HNMR (Jeol Instruments, Peabody, MA).
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 16 h; A mixture of 3,6-dibromo-9H-carbazole (3.0 g, 9.2 mmol), phenylboronic acid (3.0 g, 25 mmol), Pd(PPh3)4 (0.3 g, 0.26 mmol) and potassium carbonate (6.5 g, 47 mmol) in dioxane/water (75 mL/15 ml) was degassed and heated at about 100 °C for about 16 hours. Upon cooling to room temperature, the whole was worked up with ethylacetate/brine, the organic was dried over Na2So4, loaded on silica gel and purified by flash column using eluents of ethyl acetate/hexane (10percent to 30percent). After removal of solvents, a white solid (Compound 11 ) was obtained (2.1 g, in 63percent yield).
48% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 10 h; Inert atmosphere 30 g (92.3 mmol) of 3,6-dibromo-9H-carbazole was dissolved in 0.3 L of tetrahydrofuran (THF) in a nitrogenenvironment, 28 g (231 mmol) of phenyl boronic acid and 3.2 g (2.8 mmol) of tetrakis(triphenylphosphine)palladium wereadded thereto, and the mixture was agitated. 40.8 g (277 mmol) of potassium carbonate saturated in water was addedthereto, and the mixture was heated and refluxed at 80 °C for 10 hours. When the reaction was terminated, water wasadded to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and treated with anhydrousMgSO4 to remove moisture and then, filtered and concentrated under a reduced pressure. The obtained residue wasseparated and purified through flash column chromatography, obtaining a compound I-4 (14.3 g, 48 percent). HRMS (70 eV, EI+): m/z calcd for C24H17N: 319.1361, found: 319.1. HRMS (70 eV, EI+): m/z calcd for C24H17N: 319.1361, found: 319.1.
33% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 4 h; Inert atmosphere General procedure: Under nitrogen protection system, 3-bromo -9H- carbazole 1.6mmol, tetrakistriphenylphosphine palladium 0.64mmol, anhydrous carbonatePotassium1.92mmol phenylboronic acid 1.92mmol, was dissolved in N, N- dimethylformamide: H2O = (15ml: 2ml) mixed solvent,80 stirring for 4h, after completion of the reaction, cooled to room temperature, the mixed solution was extracted with dichloromethane and water, the organic phase was dried over anhydrous magnesiumDried and evaporated, evaporated and the product after column chromatography to obtain 3-phenyl -9H- carbazole (A-1) 1.44mmol, 90percent yield. The method of the same A-1, by column chromatography to obtain a white solid product 3,6-diphenyl -9H- carbazole (A-2), producingRate of 33percent.
38 g
Stage #1: With sodium carbonate In 1,4-dioxane; water for 1 h; Inert atmosphere
Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In 1,4-dioxane; waterReflux; Inert atmosphere
3,6-dibromocarbazole (50 g, 0.154 mol), phenylboronic acid (41 g, 0.336 mol), 150ml water, 80g sodium carbonate, and 600ml dioxane were charged into a 2 liter pot with magnetic stirrer, reflux condenser and nitrogen inlet, and sparged with nitrogen for one hour. Pd2DBA3 (6g, 0.0066mol) and tri-t-butylphosphine (3 g, 0.0148mol) was quickly added from the drybox. The reaction was refluxed overnight. The next day water was added to the reaction mixture and methylene chloride extractions were preabsorbed to 141 g of activated silica and purified by column chromatography using methylene chloride/hexanes yielding 38 grams of product 3,6-diphenylcarbazole.

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