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Product Details of [ 1024598-06-8 ]

CAS No. :1024598-06-8 MDL No. :MFCD22581305
Formula : C24H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :IENOQUQIVSMWGP-UHFFFAOYSA-N
M.W : 332.40 Pubchem ID :59365871
Synonyms :

Calculated chemistry of [ 1024598-06-8 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 26
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 110.14
TPSA : 20.72 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 : No
Log Kp (skin permeation) : -3.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.4
Log Po/w (XLOGP3) : 6.46
Log Po/w (WLOGP) : 6.42
Log Po/w (MLOGP) : 5.02
Log Po/w (SILICOS-IT) : 5.58
Consensus Log Po/w : 5.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.64
Solubility : 0.0000753 mg/ml ; 0.000000227 mol/l
Class : Poorly soluble
Log S (Ali) : -6.69
Solubility : 0.0000679 mg/ml ; 0.000000204 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.18
Solubility : 0.000000218 mg/ml ; 0.0000000007 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 1024598-06-8 ]

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 [ 1024598-06-8 ]

* 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 [ 1024598-06-8 ]
  • Downstream synthetic route of [ 1024598-06-8 ]

[ 1024598-06-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 108-86-1 ]
  • [ 60511-85-5 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
83% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 160℃; for 48 h; Pd2 (dba) 3 178.6 mg (0.20 mmol) and t-Bu3P 78.9 mg (0.39 mmol) of o-xylene (o-xylene) was dissolved in 50 ml after 10 bungan room temperature in agitation. 11,12-dihydroindolo-[2,3-a] carbazole (Intermediate I-1) 5 g (19.51 mmol), bromobenzene 3.37g (21.46 mmol), and t-BuONa 1.12 g (11.71 mmol) It was added and stirred for 48 hours at reflux at 160°C . 20 ml of distilled water after the cold reaction and extracted with ethyl acetate. After filtering the solvent was evaporated and dried with magnesium sulfate. After column (11,12-dihydroindolo[2,3-a]carbazole] carbazole) Intermediate I-2 through the chromatography to obtain 5.35 g (yield 83percent). MS-EI, m / e, 332.13 (calculated), 332.19 (measured value).
75% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene for 24 h; Inert atmosphere; Reflux 100.00 g (390.19 mmol) of Intermediate 1, 73.52 g, (468.23 mmol) of bromobenzene, 75.00 g (780.39 mmol) of sodium t-butoxide, 22.44 g (32.02 mmol) of tris(dibenzylideneacetone) dipalladium, and 31.58 g (50percent in toluene) of tri t-butylphosphine were mixed with 1.5 L of xylene in a 3 L flask, and the mixture was heated and refluxed under a nitrogen flow for 24 hours. The obtained mixture was added to 4.5 L of methanol, and a solid crystallized therein was filtered, dissolved in monochlorobenzene, filtered with silica gel/Celite, and after removing an appropriate amount of an organic solvent, recrystallized with methanol to obtain 97.0 g of Intermediate 2 (a yield of 75percent).
73% With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 17 h; Inert atmosphere In a nitrogen atmosphere 11,12-dihydroindolo [2,3-a] carbazole (50.0 g, 0.19 mol),bromobenzene (15.3 g, 0.10 mol),bis(tri-tert-butylphosphine)palladium (0) (0.99 g, 1.95 mmol), and sodium tert-butoxide (28.1 g, 0.29 mol) were placed in 750 mL of xylene and heated and stirred for 17 hours. The reaction mixture was cooled to room temperature and filtered to remove salts. The xylene was concentrated under reduced pressure, and the resultant product was subjected to column purification using a mixed solution of tetrahydrofuran and hexane to obtain the intermediate A (47.6 g, yield 73percent, MS: [M+=333).
44% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 15 h; Inert atmosphere; Reflux 39.99 g (156.01 mmol) of indolocarbazole, 26.94 g (171.61 mmol) of bromobenzene, 22.49 g (234.01 mmol) of sodium t-butoxide, 4.28 g (4.68 mmol) of tris(dibenzylideneacetone)dipalladium, and 2.9 mL of tri-t-butylphosphine (50percent in toluene) were added to 500 mL of xylene in a 1,000-mL round-bottom flask, and mixed and heated under reflux in a nitrogen atmosphere for about 15 hours. The resulting mixture was added to 1,000 mL of methanol to obtain crystalline solid powder by filtering. The resulting product was dissolved in dichlorobenzene and filtered using Silica gel/Celite, followed by removing an appropriate amount of the organic solvent and recrystallization with methanol to obtain Intermediate B2 (23.01 g, Yield: 44percent). calcd. C24H16N2 : C, 86.72; H, 4.85; N, 8.43; found : C, 86.72; H, 4.85; N, 8.43
44% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene for 15 h; Inert atmosphere; Reflux In 1000 mL round bottom flask with carbazole indole 39.99 g (156.01 mmol), bromobenzene 26.94 g (171.61 mmol), sodium t-Butoxide 22.49 g (234.01 mmol), tris (dibenzylideneacetone) di palladium 4.28 g (4.68 mmol) and tri t-Butylphosphine heating pin mixing 2.9 mL (50percent in toluene) and 500 mL of xylene and refluxed for 15 hours under a nitrogen flow toIt was. After the resultant mixture from which the crystallized solid was filtered, added to 1000 mL of methanol, the-dichlorobenzeneMelt filtration with silica gel / Celite, and an appropriate amount of the organic solvent was removed, and recrystallized with methanol to Intermediate B2 (23.01g, was obtained in 44percent yield).
44% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 15 h; Inert atmosphere; Reflux 1000 ml of indolocarbazole 39.99 g of a roundbottom flask (156.01 mmol ), bromobenzene 26.94 g (171.61 mmol), sodiumt-butoxide 22.49 g (234.01 mmol ), tris (dibenzylideneacetone) dipalladium 4.28g (4.68 mmol) and tri-t-butylphosphine 2.9 mL (50percent in toluene) in 500 ml of xylene mixed with a nitrogen flow for 15 hours under reflux byheating. The mixture obtained therefrom is added to the methanol of 1000 mlfiltered and then crystallized solids, dichlorobenzene at benzene a silicagel/filtered through celite and after removal of the amount of the organicsolvent, a recrystallization from methanol and the intermediate B2 (23.01 g,44percent yield).

Reference: [1] Patent: KR2015/96018, 2015, A, . Location in patent: Paragraph 0377-0379
[2] Patent: US2018/90690, 2018, A1, . Location in patent: Paragraph 0161; 0162
[3] Patent: KR2018/32519, 2018, A, . Location in patent: Paragraph 0120-0122
[4] Patent: EP2894157, 2015, A1, . Location in patent: Paragraph 0198
[5] Patent: KR2015/84657, 2015, A, . Location in patent: Paragraph 1642-1645
[6] Patent: KR2015/84558, 2015, A, . Location in patent: Paragraph 0539-0541
  • 2
  • [ 1361125-94-1 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
71.5% With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 12 h; Inert atmosphere In 250ml three-necked flask, under nitrogen protection, 0.04mol intermediate 1.0.05mol triphenylphosphine was added,100ml o-dichlorobenzene, stirred and mixed, heated to 180 , the reaction 12 hours,Sampling point plate, showing no intermediate 1 remaining,The reaction was complete; naturally cooled to room temperature, filtered, the filtrate was evaporated to a distillate free, over a neutral silica gel column to give Intermediate 2, HPLC purity of 99.2percent, a yield of 71.5percent;
Reference: [1] Patent: CN107353290, 2017, A, . Location in patent: Paragraph 0046; 0048
  • 3
  • [ 855180-11-9 ]
  • [ 244205-40-1 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
78.4%
Stage #1: With hydrogen bromide; dihydrogen peroxide In water; acetonitrile at -20℃;
Stage #2: With palladium diacetate; caesium carbonate; (RP,RP)-1,2-bis[(o-anisyl)(phenyl)phosphino]ethane In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere; Reflux
77.5 g (0.3 mol) of 1-amino-N-phenylcarbazole was dissolved in 300 mL of acetonitrile in a 2 L three-necked flask.Add 52.6 g (0.26 mol) mass percent 40percent hydrobromic acid aqueous solution,Control the reaction temperature to slowly add 27.6 mL (0.27 mol) of 30percent hydrogen peroxide at -20 °C.After the addition is complete, the natural temperature is raised overnight.The reaction solution is washed with an aqueous solution of sodium hydrogen sulfite,Divide the organic layer,Add hydrochloric acid to get1-amino-2-bromo-N-phenyloxazole hydrochloride,97.1 g after drying;Under argon protection,Will be 97.1 g (0.25 mol)1-amino-2-bromo-N-phenyloxazole hydrochloride,50.2 g (0.25 mol) o-bromobenzeneboronic acid,36.9 g of Caesium carbonate,250 mL of N-methylpyrrolidone solvent was added to a 2 L three-necked flask.Replacement air system,Then control 0.05g of palladium acetate and 0.23g at 20 °C(R,R)-1,2-bis[(2-methoxyphenyl)phenylphosphino]ethane,Refluxreaction,Liquid chromatograph detection,After the end, add 300 mL of ice water to stop the reaction.Extracted with 300 mL of dichloromethane,Wash the organic layer with sodium hydroxide solution,Dry over anhydrous sodium sulfate overnight.Concentrated to a crude product,300 mL of xylene-210 mL methanol mixed solvent was recrystallized twice to obtain a product.11,12-Dihydro-11-phenylindolo[2,3-a]carbazole 78.2 g,The content is 99.5percent, and the total yield is 78.4percent
Reference: [1] Patent: CN108148065, 2018, A, . Location in patent: Paragraph 0011; 0013; 0014
  • 4
  • [ 591-50-4 ]
  • [ 60511-85-5 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
65% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 3 h; Inert atmosphere; Reflux According to the preparation method of compound 66 in Example 3,the difference is,The synthetic route used is the above route,Using compound 113 'instead of carbazole,Using iodobenzene instead of compounds 1-5,To give compound 113-1 (yield 65percent)
Compound 1-5 (0.1623 mol) was added to toluene (450 mL)And then carbazole (0.1623 mol) was added under nitrogen protection,Sodium tert-butoxide (0.3246 mol), Pd2 (dba) 3 (0.0016 mol)And tri-tert-butylphosphine (0.0016 mol)And heated to reflux for 3 h,The silica gel funnel was filtered and the resulting filtrate was evaporated to dryness. The resulting solid was recrystallized from toluene to give compound 66 (yield 48percent):
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 12 h; Reflux; Inert atmosphere to a 2-neck round bottom flask under nitrogen a mixture of B-1 2.1g (0.0082mol), iodo- benzene (Iodobenzene) 2.5g(0.013mol), Cu 0.312g (0.0049), 18- crown-6-ether (18-crown- 6-ether) 0.433g (0.0016mol), K2CO3 3.397g (0.0246mol) and o-DCB 20ml was stirred under reflux for 12 hours.The solution cooled to room temperature was extracted and concentrated by MC / H2O and separated with column chromatography (SiO2, Hexane:ethyl acetate = 10: 1) to obtain the title compound 2-B (1.76g, 64percent) as a white solid.
64% With 18-crown-6 ether; copper In 1,2-dichloro-benzene for 12 h; Reflux; Inert atmosphere Under nitrogen Two neck round bottom flask (rbf two neck: two neck round bottom flask) to the C-1 (2.1g, 0.0082mol), iodo- benzene (Iodobenzene) (2.5g, 0.013mol), Cu (0.312g , .0049), 18-crown-6-ether (18-Crown-6-ether) (0.433g, 0.0016mol), potassium carbonate (3.397g, 0.0246mol), ortho-dichlorobenzene in the mixture (20ml), It was stirred under reflux for 12 hour. Concentrated by extracting the solution cooled to room temperature with methylene chloride / H2O and purified by column chromatography (SiO2, hexane: ethyl acetate = 10: 1) to obtain a white solid compound C-2 by (1.76g, 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzeneInert atmosphere; Reflux Under nitrogen tunek round bottom flask (two neck round bottom flask) to A-1 (2.1g, 0.0082mol), Iodobenzene 2.5g (0.013mol), Cu 0.312g (0.0049 mol), 18-crown-6-ether 0.433g (0.0016mol), 20 ml of o-dichlorobenzene,K2CO3 (3.397g, 0.0246mol) was stirred under reflux for 16 hours . The solution was cooled to room temperature, MC (methylene chloride) / H2O and extracted with concentrated and separated by column chromatography (SiO2, hexane,ethyl acetate) 1/10) to give a white solid compound A-2 (1.76g , 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzeneReflux The compounds in the original neck rbf a nitrogen filled 250-2 (2.1g, 1.0eq), iodo-benzene (2.5g, 1.5eq), Cu (0.312g, 0.6eq), 18- crown-6-ether (0.433g , 0.2eq), a mixture of K2CO3 (3.397g, 3.0eq), 1,2- dichlorobenzene (20) was stirred for 16 hours at reflux temperature. The solution was concentrated and cooled to room temperature and extracted with MC / H2O and purified by column chromatography (SiO2, hexane: 1: ethyl acetate = 10) to obtain a white solid compound 250-3 separated by (1.76g, 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 16 h; Reflux A mixture of compound 73-2 (2.1 g, 1.0 equiv.),Iodobenzene (2.5 g, 1.5 eq.),Cu (0.312 g, 0.6 equiv),18-Crown-6-ether (0.433 g, 0.2 equiv),K2CO3 (3.397 g, 3.0 eq)And 1,2-dichlorobenzene (20 ml) was stirred at reflux temperature for 16 hours.The solution cooled to room temperature was extracted with MC / H2O and concentrated,And then purified by column chromatography (SiO2, hexane: ethyl acetate = 10: 1)Compound 73-3 (1.76 g, 64percent) was isolated as a white solid.
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 16 h; Inert atmosphere; Reflux A mixture of Compound B-1 (2.1 g, 0.0082 mol), iodobenzene (2.5 g, 0.013 mol), Cu (0.312 g, 0.0049), 18-crown-6-ether (0.433 g, 0.0016 mol), K2CO3(3.397 g, 0.0246 mol), and o-dichlorobenzene (o-DCB) (20 ml) was refluxed and stirred in a two neck round bottom flask (two neck r.b.f) under nitrogen for 16 hours. The mixed solution cooled to room temperature was extracted with MC (methylene chloride)/H2O and concentrated and separated by column chromatography (SiO2, hexane:ethyl acetate=10:1). As a result, a white solid compound B-2 was obtained (1.76 g, 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzeneInert atmosphere; Reflux Under nitrogen, compound B-1 (2.1 g, 0.0082 mol), Iodobenzene (2.5 g, 0.013 mol), Cu (0.312 g, 0.0049), 18-crown-6-ether (0.433 g, 0.0016 mol), and K2CO3 (3.397g, 0.0246 mol) in o-dichlorobenzene (o-DCB) (20 ml) was stirred at reflux condition for 16 hours. The solution cooled to room temperature was extracted with dichloromethane/H2O, concentrated and subjected to column chromatography (SiO2, hexane:ethyl acetate=10:1) to obtain white solid compound B-2 was obtained (1.76 g, 64percent).
64% With 18-crown-6 ether; copper; potassium carbonate In 1,2-dichloro-benzene for 12 h; Reflux; Inert atmosphere To a 2 neck round bottom flask under nitrogen was added the compound B-1 (2.1 g, 0.0082 mol), iodobenzene (Iodobenzene, 2.5 g,0.013 mol), Cu (0.312 g, 0.0049 mol), 18-crown-6-ether (0.433 g, 0.0016 mol)A mixture of o-DCB (20 ml) of K2CO3 (3.397 g, 0.0246 mol) was refluxed for 12 hours. The solution cooled to room temperature was washed with MC / H2O, And concentrated by column chromatography (SiO2, hexane: Ethyl acetate = 10: 1) to obtain white solidWater B-2 was obtained (1.76 g, 64percent).
64% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 3 h; Reflux; Inert atmosphere The intermediate of indolocarbazole, benzene iodide (1.1 equivalent), bisdibenzylidene acetone palladium (0) (0.03 equivalent), tri-t-butylphosphine (1 equivalent), and sodium t-butoxide (2 equivalent) was added to toluene under an nitrogen environment, and the mixture was heated and refluxed for 3 hours. When a reaction was complete, the reaction solution was once filtered at a high temperature, twice extracted with brine, and an organic layer extracted therefrom was dried and concentrated. The concentrated solution was added to methanol in a dropwise fashion to obtain a solid, and a residue obtained after filtering the solid was separated and purified through column chromatography to obtain Intermediate of phenyl-indolocarbazole (64percent).
41% at 190℃; for 72 h; Inert atmosphere Example 1; Synthesis of Compound 1-19; Under a nitrogen atmosphere, 26.0 g (0.10 mol) of IC-1, 122.7 g (0.60 mol) of iodobenzene, 54.7g (0.29 mol) of copper iodide, 66.7 g (0.48 mol) of potassium carbonate, and 800 ml of quinoline were stirred for 72 hours while being heated at 190°C. The reaction solution wascooled toroomtemperature. Afterthat, distilledwater (500 ml) and dichloromethane (500 ml) were then added while being stirred. The precipitated crystal was separated by filtration. The organic layer was then washed with distilled water (3.x.500 ml). The organic layer was dried over anhydrous magnesium sulfate. The magnesium sulfate was then separated by filtration and the solvent was subjected to vacuum distillation. The resultant residue was purified by silica gel column chromatography to afford 13.7 g (41percent yield) of an intermediate B as a white solid.
40.6% at 190℃; for 72 h; In a 1000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 26.0 g (101.4 mmol) of the white powder obtained above, 122.7 g (601.4 mmol) of iodobenzene, 54.7 g (287.2 mmol) of copper iodide, 66.7g (482.6 mmol) of potassium carbonate, and 800 ml of quinoline and stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were filtered. The filtrate was transferred to a 2000-ml separatory funnel and separated into the organic layer and the aqueous layer. The organic layer was washed three times with 500 ml of water, dehydrated over magnesium sulfate, the magnesium sulfate was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (41.2 mmol, 40.6percent yield) of a white powder.; Then, 26.0 g (101.4 mmol) of the white powder obtained above, 122.7 g (601.4 mmol) of iodobenzene, 54.7 g (287.2 mmol) of copper iodide, 66.7 g (482.6 mmol) of potassium carbonate, and 800 ml of quinoline were placed in a 1000-ml three-necked flask that had been deaerated and filled with nitrogen and stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were filtered. The filtrate was transferred to a 2000-ml separatory funnel and separated into the organic layer and the aqueous layer. The organic layer was washed three times with 500 ml of water, dehydrated over magnesium sulfate, the magnesium sulfate was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (41.2 mmol, 40.6percent yield) of a white powder.; Then, 26.0 g (0.101 mole) of the white powder obtained above, 122.7 g (0.601 mole) of iodobenzene, 54.7 g (0.287 mole) of copper iodide, 66.7 g (0.482 mole) of potassium carbonate, and 800 ml of quinoline were placed in a 1000-ml three-necked flask that had been deaerated and filled with nitrogen and stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were filtered. The filtrate was transferred to a 2000-ml separatory funnel and separated into the organic layer and the aqueous layer. The organic layer was washed three times with 500 ml of water, dehydrated over magnesium sulfate, the magnesium sulfate was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (0.04 mole, 40.8percent yield) of a white powder.
40.6% With potassium carbonate In quinoline at 190℃; for 72 h; In a 1000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 26.0 g (101.4 mmoles) of the white powder obtained above, 122.7 g (601.4 mmoles) of iodobenzene, 54.7 g (287.2 mmoles) of copper iodide, and 66.7 g (482.6 mmoles) of potassium carbonate, then 800 ml of quinoline was added, and the mixture was stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were filtered. The filtrate was transferred to a 2000-ml separatory funnel and separated into an organic layer and an aqueous layer. The organic layer was washed three times with 500 ml of water and dried over magnesium sulfate, the magnesium sulfate was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (41.2 mmoles, 40.6percent yield) of white solid A or 11-phenylindolo[2,3-a]carbazole.
40.8% at 190℃; for 72 h; Inert atmosphere Next, in a 1,000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 26.0 g (0.101 mole) of the white powder A obtained above, 122.7 g (0.601 mole) of iodobenzene, 54.7 g (0.287 mole) of copper iodide, 66.7 g (0.482 mole) of potassium carbonate, and 800 ml of quinoline and stirred. The mixture was then heated to 190°C and stirred at this temperature for 72 hours. The mixture was cooled to room temperature, 500 ml of water and 500 ml of dichloromethane were added, the mixture was stirred, and the yellow crystals formed were collected by filtration. The filtrate was transferred to a 2,000-ml separatory funnel and separated into an organic layer and an aqueous layer. The organic layer was washed three times with 500 ml of water and then dehydrated over magnesium sulfate, the magnesium sulfate was filtered out, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to give 13.7 g (0.04 mole, 40.8percent yield) of a white powder B.
40.6% at 190℃; for 72 h; Inert atmosphere Next, 26.0 g (0.10 mol) of the white powder obtained in the foregoing, 122.7 g (0.60 mol) of iodobenzene, 54.7 g (0.29 mol) of copper iodide, 66.7 g (0.48 mol) of potassium carbonate, and 800 ml of quinoline were loaded into a 1,000-ml three-necked flask purged with nitrogen and stirred. After that, the mixture was heated to 190° C. and stirred for 72 hr. Once the mixture was cooled to room temperature, and then 500 ml of water and 500 ml of dichloromethane were added to the mixture, followed by stirring. After that, the resultant yellow crystal was taken by filtration. The filtrate was transferred to a 2,000-ml separating funnel, and was fractionated into an organic layer and an aqueous layer. The organic layer was washed with 500 ml of water three times, and then the resultant organic layer was dried with magnesium sulfate. Once magnesium sulfate was separated by filtration and then the solvent was distilled off under reduced pressure. After that, the residue was purified by column chromatography to provide 13.7 g (0.041 mol, yield: 40.6percent) of Intermediate A as a white solid.

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  • 5
  • [ 591-50-4 ]
  • [ 222-19-5 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
51% With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane for 24 h; Inert atmosphere; Reflux In an argon atmosphere, 90 ml of dehydrated 1,4-dioxane was added to a mixture of 15.0 g (58.5 mmol) of indolo[2,3-a]carbazole (synthesized according to the method of Synlett p.42-48 (2005)), 11.9 g (58.5 mmol) of iodobenzene, 11.2 g (58.5 mmol) of copper iodide, 20.0 g (175.5 mmol) of trans-1,2-cyclohexanediamine, and 37.3 g (175.5 mmol) of tripotassium phosphate, and the resultant mixture was stirred for 24 h while refluxing under heating. The reaction solution was concentrated under reduced pressure. The obtained residue was added with 500 ml of toluene, heated to 120 °C, and then filtered to remove insolubles. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography, to obtain 10.0 g of white solid, which was identified as the following intermediate 2-1 by FD-MS analysis (yield: 51percent).
Reference: [1] Patent: EP2738166, 2014, A1, . Location in patent: Paragraph 0167
  • 6
  • [ 108-86-1 ]
  • [ 13716-12-6 ]
  • [ 60511-85-5 ]
  • [ 1024598-06-8 ]
YieldReaction ConditionsOperation in experiment
55% With tris-(dibenzylideneacetone)dipalladium(0) In water; toluene First step; Synthesis of 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole
78.35 g (305.69 mmol) of 11,12-dihydroindolo[2,3-a]carbazole, 26.8 mL (254.74 mmol) of bromobenzene, 26.93 g (280.22 mmol) of NaOt-Bu, and 7 g (7.64 mmmol) of Pd2(dba)3 were suspended in 1400 ml of toluene, 3.64 ml (15.28 mmol) of P(t-Bu)3 was added thereto, and the mixture was refluxed and agitated for 12 hours.
Distilled water was added thereto for extraction, and an organic layer produced therein was filtered with silica gel.
After removing an organic solution therefrom, a solid product was recrystallized with dichloromethane and n-hexane, obtaining 46.2 g of 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole (a yield : 55 percent, LC Mass M+H+ = 333.13).
Reference: [1] Patent: EP2821459, 2015, A2, . Location in patent: Page/Page column
  • 7
  • [ 59-88-1 ]
  • [ 1024598-06-8 ]
Reference: [1] Patent: EP2415772, 2012, A1,
[2] Patent: KR2015/132019, 2015, A,
[3] Patent: KR101551895, 2015, B1,
  • 8
  • [ 1361125-94-1 ]
  • [ 1024598-06-8 ]
  • [ 1316311-27-9 ]
Reference: [1] Journal of Materials Chemistry C, 2018, vol. 6, # 21, p. 5812 - 5820
  • 9
  • [ 1001911-63-2 ]
  • [ 1024598-06-8 ]
Reference: [1] Patent: CN107353290, 2017, A,
[2] Journal of Materials Chemistry C, 2018, vol. 6, # 21, p. 5812 - 5820
  • 10
  • [ 577-19-5 ]
  • [ 1024598-06-8 ]
Reference: [1] Patent: CN107353290, 2017, A,
[2] Journal of Materials Chemistry C, 2018, vol. 6, # 21, p. 5812 - 5820
  • 11
  • [ 765-87-7 ]
  • [ 1024598-06-8 ]
Reference: [1] Patent: EP2415772, 2012, A1,
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