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[ CAS No. 61822-18-2 ] {[proInfo.proName]}

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Chemical Structure| 61822-18-2
Chemical Structure| 61822-18-2
Structure of 61822-18-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 61822-18-2 ]

CAS No. :61822-18-2 MDL No. :MFCD28154716
Formula : C14H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OFGBQGFYHXYVIA-UHFFFAOYSA-N
M.W : 227.26 Pubchem ID :12339399
Synonyms :

Calculated chemistry of [ 61822-18-2 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 13
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 68.79
TPSA : 34.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 3.33
Log Po/w (WLOGP) : 3.34
Log Po/w (MLOGP) : 2.09
Log Po/w (SILICOS-IT) : 3.56
Consensus Log Po/w : 2.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.78
Solubility : 0.0376 mg/ml ; 0.000166 mol/l
Class : Soluble
Log S (Ali) : -3.73
Solubility : 0.0427 mg/ml ; 0.000188 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.22
Solubility : 0.00136 mg/ml ; 0.000006 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 61822-18-2 ]

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 [ 61822-18-2 ]

* 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 [ 61822-18-2 ]

[ 61822-18-2 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 61822-18-2 ]
  • [ 552860-96-5 ]
YieldReaction ConditionsOperation in experiment
85% With N-Bromosuccinimide In chloroform; acetic acid at 20℃; for 12h;
Multi-step reaction with 2 steps 1.1: 67 percent / bromine / acetic acid / 100 °C 2.1: butyllithium / tetrahydrofuran / -78 °C 2.2: H2O / tetrahydrofuran
With N-Bromosuccinimide In tetrahydrofuran at 0 - 20℃; 7 Synthesis example 7 3,6-dibromo-2,7-dimethoxycarbazole In a flask, covered with aluminum foil, a stirred solution of 1.48 g (6.5 mmol) 2,7-dimethoxycarbazole in 60 ml tetrahydrofuran was cooled to 0 °C. 2.3 g (13 mmol) N-bromosuccinimide was added in small portions. The mixture was allowed to warm to room temperature overnight. THF was evaporated and the product was used without further purification. 1H NMR (DMSO-d6): δ 11.30 (s, 1H), 8.30 (s, 2H), 7.13 (s, 2H), 3.90 (s, 6H). 13C NMR (DMSO-d6): δ 153, 140, 123, 116, 102, 94, 56.
  • 2
  • [ 61822-18-2 ]
  • [ 758716-63-1 ]
YieldReaction ConditionsOperation in experiment
67% With bromine In acetic acid at 100℃;
  • 3
  • [ 61822-18-2 ]
  • [ 552860-97-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / N-bromosuccinimide / CHCl3; acetic acid / 12 h / 20 °C 2: 95 percent / sodium hydroxide / tetrabutylammonium hydrogen sulfate / acetone / 24 h / Heating
  • 4
  • [ 61822-18-2 ]
  • 2,7-dihydroxy-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine hydrochloride In water 1.A A. A. Preparation of 2,7-dihydroxy-9H-carbazole 2,7-Dimethoxy-9H-carbazole (1.94 g; prepared according to the process described in M. H. Litt, et al., Macromolecules, 18, p. 1388 (1985)) was mixed with pyridine hydrochloride (6.39 g) and the resulting mixture was stirred at 232° C. for 20 minutes. The reaction liquid was cooled to room temperature. Water was added to the mixture to precipitate a crude product, which was then washed with water and dried under reduced pressure at 60° C. to yield the title compound (1.50 g). Rf=0.27 (1:1 hexane/ethyl acetate); 1H-NMR (CDCl3): 10.61 (1H, br), 9.13 (2H, s), 7.64 (2H, d, J=8.3), 6.71 (2H, d, J=2.0), 6.53 (2H, dd, J=8.3, 2.0); Mass (m/e): 199 (M+).
  • 5
  • [ 61822-18-2 ]
  • [ 696-62-8 ]
  • [ 815632-42-9 ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate In 1,2-dichloro-benzene for 20h; Heating / reflux; 26 Synthesis example 26 2,7-dimethoxy-9-(4-methoxyphenyl)carbazole A mixture of 0.5 g (2 mmol) 2,7-dimethoxycarbazole, 1.0 g (4 mmol) 4-iodoanisole, 0.35 g (2.5 mmol) potassium carbonate, 0.15 g (2 mmol) copper and 23 mg 18-crown-6 in 5 ml 1,2-dichlorobenzene was evacuated, charged with argon and refluxed during 20 hours. Afterwards, the reaction mixture was allowed to cool to room temperature and filtered. Then an extraction of the filtrate using toluene and water was performed, followed by drying the organic layer over MgSO4, filtration and evaporation of the solvents. 0.64 g (86 %) of product was obtained after column chromatography (SiO2, gradient from pure hexane to pure dichloromethane) followed by crystallisation from dichloromethane and methanol. 1H NMR (CDCl3): δ 7.90 (d, J=8 Hz, 2H), 7.44 (d, J=8 Hz, 2H), 7.12 (d, J=8 Hz, 1H), 6.86 (dd, J=1.5 Hz, J=8 Hz, 2H), 6.75 (d, J=1.5 Hz, 2H), 3.92 (s, 3H), 3.82 (s, 6H). 13C NMR (CDCl3): δ 159, 158, 143, 130, 129, 120, 117, 115, 108, 94, 56, 56. mp: 143 °C.
  • 6
  • [ 61822-18-2 ]
  • [ 529-28-2 ]
  • [ 890079-92-2 ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate In 1,2-dichloro-benzene for 40h; Heating / reflux; 27 Synthesis example 27 2,7-dimethoxy-9-(2-methoxyphenyl)carbazole A mixture of 0.5 g (2 mmol) 2,7-dimethoxycarbazole, 1.0 g (4 mmol) 2-iodoanisole, 0.35 g (2.5 mmol) potassium carbonate, 0.15 g (2 mmol) copper and 23 mg 18-crown-6 in 5 ml 1,2-dichlorobenzene was evacuated, charged with argon and refluxed during 40 hours. Afterwards, the reaction mixture was allowed to cool to room temperature and filtered. Then an extraction of the filtrate using toluene and water was performed, followed by drying the organic layer over MgSO4, filtration and evaporation of the solvents. 0.6 g (81 %) of product was obtained after column chromatography (SiO2, gradient from pure hexane to pure dichloromethane). 1H NMR (CDCl3): δ 7.90 (d, J=8 Hz, 2H), 7.50 (dt, J=1.5 Hz, J=8 Hz, 1H), 7.45 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.18 (dd, J=1.5 Hz, J=8 Hz, 1H), 7.16 (dt, J=1.5 Hz, J=8 Hz, 1H), 6.86 (dd, J=1.5 Hz, J=8 Hz, 2H), 6.58 (d, J=1.5 Hz, 2H), 3.82 (s, 6H), 3.73 (s, 3H). 13C NMR (CDCl3): δ 158, 156, 143, 130, 130, 126, 121, 120, 117, 113, 108, 95, 56. mp: 148°C.
  • 7
  • [ 13606-06-9 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
86% With 1,10-Phenanthroline; sodium palladium(II) tetrachloride; formyloxybenzene; sodium salt of phosphorous acid In N,N-dimethyl-formamide at 170℃; for 5h; Inert atmosphere; Schlenk technique; Sealed tube; 2.3. General procedure for catalytic reactions General procedure: The catalyst precursors were handled, weighed and stored inthe air except for Pd(OAc)2 that was stored under dinitrogen. Inorder to avoid weighing very small amounts of the catalysts, stocksolutions (under dinitrogen) of palladium catalysts were preparedin the appropriate solvent. For catalytic runs that required anamount of Phen less than 10 mg, a stock solution was preparedto avoid large weighing errors. In a typical reaction, the substratewas weighed in the air and placed in a 23 mL heavy-walled glasspressure tube with screw thread (Duran) containing a magneticstirring bar. (For an in-depth discussion of the different kinds ofpressure tubes that can be employed, and the correspondingadvantages and disadvantages see ref. [33]). The tube was placedin a Schlenk tube with a wide mouth. The tube was evacuatedand filled with dinitrogen three times to remove air. The catalystand ligand solutions and the amount of solvent required to reacha total volume of 10 mL were added and the reaction mixturewas stirred for 10 min to allow Phen to coordinate to palladium.Finally, HCOOPh and the base were added in this order. The pressuretube was plugged with a Schott PTB screw cap completed witha PTFE-protected seal and immersed in an oil bath preheated at theappropriate temperature. At the end of the reaction, the pressuretube was lifted from the oil and let to cool to room temperature.Then, the screw cap was carefully removed, the excess of CO wasvented, and the content was analyzed by GC or subjected to columnchromatography. (Caution: evolution of dissolved CO fromthe solution may continue for several minutes; keep the tubeunder a hood).
82% With triethyl phosphite at 160℃; for 16h; Inert atmosphere;
81% With triethyl phosphite at 200℃; for 0.166667h; Microwave irradiation;
75% With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane In acetic acid butyl ester at 120℃; for 12h;
74% With triethyl phosphite for 16h; Heating / reflux; 6 Synthesis example 6 2,7-dimethoxycarbazole 10 g (38.6 mmol) 4,4'-dimethoxy-2-nitro-1,1'-biphenyl in 35 ml triethylphosphite is refluxed during 16 hours in argon atmosphere. The mixture was allowed to cool to room temperature, upon which the product precipitates. Filtration and washing with methanol gave 6.5 g (74 %) of a white solid. 1H NMR (DMSO-d6): δ 11.00 (s, 1H), 7.85 (d, J=8 Hz, 2H), 6.94 (d, J=1.5 Hz, 2H), 6.74 (dd, J=1.5 Hz, J=8 Hz, 2H), 3.82 (s, 6H). 13C NMR (DMSO-d6): δ 157, 141, 119, 116, 107, 94, 55. mp: 285 °C.
70.1% With triethyl phosphite at 170℃; for 4h; Inert atmosphere;
68% With phenyl magensium bromide In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere;
60% With triethyl phosphite at 140℃; Sealed tube;

  • 8
  • [ 92248-06-1 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
90% With copper diacetate; palladium diacetate; In N,N-dimethyl-formamide; at 130℃; for 1.16667h;Inert atmosphere; Microwave irradiation; General procedure: A mixture of 5a (0.100 g, 0.47 mmol), Pd(AcO)2 (0.0105 g,0.047 mmol) and Cu(AcO)2 (0.211 g, 1.17 mmol) in dry DMF (0.5 mL), under N2 atmosphere, wasstirred and heated at 130 C for 70 min under MW irradiation (100 W). The solvent was removed under vacuum by adding toluene, and the azeotropic distillation was continued until no solventremained. The residue was purified by column chromatography over silica gel (10 g/g of crude,hexane/EtOAc, 95:5), to give 1h (0.079 g, 80%) as a white solid.
  • 9
  • [ 61822-18-2 ]
  • [ 1122-91-4 ]
  • [ 1220125-46-1 ]
YieldReaction ConditionsOperation in experiment
42% With tri-tert-butyl phosphine; palladium diacetate; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 6h; Inert atmosphere;
  • 10
  • [ 5344-78-5 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper / 180 - 210 °C 2: triethyl phosphite / 4 h / 170 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: tri-tert-butyl phosphine; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) / tetrahydrofuran; toluene / 24 h / 20 °C / Inert atmosphere 2: triethyl phosphite / 16 h / 160 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 25 °C 2: potassium carbonate / acetone / 10 h / 60 °C 3: triethyl phosphite / 140 °C / Sealed tube
  • 11
  • [ 61822-18-2 ]
  • [ 1283116-61-9 ]
  • [ 1338080-13-9 ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate In dimethyl sulfoxide at 150℃;
  • 12
  • [ 61822-18-2 ]
  • [ 1338080-03-7 ]
  • [ 1338080-12-8 ]
YieldReaction ConditionsOperation in experiment
50% With potassium carbonate In dimethyl sulfoxide at 150℃;
  • 13
  • [ 61822-18-2 ]
  • [ 145694-80-0 ]
  • [ 1338080-15-1 ]
YieldReaction ConditionsOperation in experiment
73% With potassium carbonate In dimethyl sulfoxide at 150℃;
  • 14
  • [ 591-50-4 ]
  • [ 61822-18-2 ]
  • 2,7-dimethoxy-9-phenyl-9<i>H</i>-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With copper(l) iodide; potassium carbonate; <i>L</i>-proline In dimethyl sulfoxide at 180℃; for 2h; Inert atmosphere;
  • 15
  • [ 67-56-1 ]
  • [ 124-41-4 ]
  • [ 136630-39-2 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
61.1% With copper(l) iodide In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere; Sealed tube;
  • 16
  • [ 61822-18-2 ]
  • [ 1416575-67-1 ]
YieldReaction ConditionsOperation in experiment
27% With (p-cymene)ruthenium(II) chloride; copper diacetate; acetic acid In 1,2-dichloro-ethane; chlorobenzene at 140℃; for 168h; Sealed tube;
  • 17
  • [ 1424799-10-9 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 9-benzyl-2,7-dimethoxy-9H-carbazole With potassium <i>tert</i>-butylate; oxygen In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 26h; Stage #2: With water In tetrahydrofuran; dimethyl sulfoxide
  • 18
  • [ 61822-18-2 ]
  • C41H29IN4NiO [ No CAS ]
  • [ 1501993-59-4 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; caesium carbonate; N-benzoyl-N'-phenylhydrazine In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;
  • 19
  • [ 61822-18-2 ]
  • [ 1415021-87-2 ]
  • [ 1501993-59-4 ]
YieldReaction ConditionsOperation in experiment
70% With copper(l) iodide; caesium carbonate; N-benzoyl-N'-phenylhydrazine In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;
  • 20
  • [ 61822-18-2 ]
  • [ 883148-62-7 ]
  • [ 1501993-62-9 ]
YieldReaction ConditionsOperation in experiment
51% With copper(l) iodide; caesium carbonate; N-benzoyl-N'-phenylhydrazine In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere;
  • 21
  • [ 61822-18-2 ]
  • [ 122-39-4 ]
  • [ 1612774-94-3 ]
YieldReaction ConditionsOperation in experiment
51% With Isopropylbenzene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; oxygen; copper diacetate In 1,1,2,2-tetrachloroethylene; acetic acid at 150℃; for 24h;
  • 22
  • [ 124-41-4 ]
  • [ 136630-39-2 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
61% With copper(l) iodide In methanol; N,N-dimethyl-formamide at 110℃; for 20h; Schlenk technique; Inert atmosphere;
  • 23
  • [ 61822-18-2 ]
  • [ 1736-85-2 ]
  • C22H20N2O4 [ No CAS ]
  • 24
  • [ 18908-66-2 ]
  • [ 61822-18-2 ]
  • 9-(2-ethylhexyl)-2,7-dimethoxycarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; potassium hydroxide In acetone Reflux;
75% With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; potassium hydroxide In acetone for 12h; Reflux;
  • 25
  • [ 61822-18-2 ]
  • 2,7-dimethoxy-3,6-bis(5-iodo-1-mesityl-1H-1,2,3-triazol-4-yl)-9-isopropylcarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2.1: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Darkness 5.1: copper(II) sulfate; sodium L-ascorbate / ethanol; water; dichloromethane / 50 °C / Inert atmosphere; Darkness 5.2: 0.5 h / 35 °C 6.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere; Schlenk technique 6.2: Inert atmosphere; Schlenk technique
  • 26
  • [ 61822-18-2 ]
  • 3,6-bis(1-mesityl-1H-1,2,3-triazol-4-yl)-9-isopropylcarbazole-2,7-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2.1: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Darkness 5.1: copper(II) sulfate; sodium L-ascorbate / ethanol; water; dichloromethane / 50 °C / Inert atmosphere; Darkness 5.2: 0.5 h / 35 °C 6.1: boron tribromide / dichloromethane / -78 - 20 °C
  • 27
  • [ 61822-18-2 ]
  • 3,6-bis(5-iodo-1-mesityl-1H-1,2,3-triazol-4-yl)-9-isopropylcarbazole-2,7-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2.1: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Darkness 5.1: copper(II) sulfate; sodium L-ascorbate / ethanol; water; dichloromethane / 50 °C / Inert atmosphere; Darkness 5.2: 0.5 h / 35 °C 6.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere; Schlenk technique 6.2: Inert atmosphere; Schlenk technique 7.1: boron tribromide / dichloromethane / 18 h / -78 - 20 °C
  • 28
  • [ 61822-18-2 ]
  • 2(3,6-bis(5-iodo-1-mesityl-1H-1,2,3-triazol-4-yl)-9-isopropylcarbazole-2,7-diol)*TBABr [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2.1: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Darkness 5.1: copper(II) sulfate; sodium L-ascorbate / ethanol; water; dichloromethane / 50 °C / Inert atmosphere; Darkness 5.2: 0.5 h / 35 °C 6.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere; Schlenk technique 6.2: Inert atmosphere; Schlenk technique 7.1: boron tribromide / dichloromethane / 18 h / -78 - 20 °C 8.1: tetrahydrofuran / 29.84 °C
  • 29
  • [ 61822-18-2 ]
  • 3,6-bis(5-iodo-1-mesityl-1H-1,2,3-triazol-4-yl)-9-isopropylcarbazole-2,7-diol*TBABr [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2.1: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Darkness 5.1: copper(II) sulfate; sodium L-ascorbate / ethanol; water; dichloromethane / 50 °C / Inert atmosphere; Darkness 5.2: 0.5 h / 35 °C 6.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere; Schlenk technique 6.2: Inert atmosphere; Schlenk technique 7.1: boron tribromide / dichloromethane / 18 h / -78 - 20 °C 8.1: tetrahydrofuran / 29.84 °C 9.1: tetrahydrofuran / 29.84 °C
  • 30
  • [ 61822-18-2 ]
  • 2,7-dimethoxy-3,6-diiodo-9-isopropylcarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere
  • 31
  • [ 61822-18-2 ]
  • 2,7-dimethoxy-3,6-bis((triisopropylsilyl)ethynyl)-9-isopropylcarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere 3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere
  • 32
  • [ 61822-18-2 ]
  • 2,7-dimethoxy-3,6-diethynyl-9-isopropylcarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere 3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Darkness
  • 33
  • [ 61822-18-2 ]
  • 2,7-dimethoxy-3,6-bis(1-mesityl-1H-1,2,3-triazol-4-yl)-9-isopropylcarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 16 h / 20 °C 2.1: N-iodo-succinimide / chloroform / 5 h / 20 °C / Darkness; Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Darkness 5.1: copper(II) sulfate; sodium L-ascorbate / ethanol; water; dichloromethane / 50 °C / Inert atmosphere; Darkness 5.2: 0.5 h / 35 °C
  • 34
  • [ 61822-18-2 ]
  • [ 75-26-3 ]
  • 2,7-dimethoxy-9-isopropylcarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With potassium hydroxide In dimethyl sulfoxide at 20℃; for 16h;
  • 35
  • [ 61822-18-2 ]
  • [ 321-38-0 ]
  • 2,7-dimethoxy-9-(naphthalen-1-yl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
12.4 g With caesium carbonate In dimethyl sulfoxide at 150℃; for 11h; Inert atmosphere; Synthesis of 2,7-dimethoxy-9-(naphthalen-1-yl)-9H-carbazole It was synthesized according to the method described in known literature 2,7-dimethoxy-9H-carbazole (10g), 1-fluoronaphthalene (9.7 g), the flask containing cesium carbonate (17.2 g) and dimethyl sulfoxide (150 ml), under a nitrogen atmosphere, this mixture was stirred for 11 hours at 150 °C. Thereafter, the reaction solution was cooled to room temperature, filtered off the precipitate by suction filtration, washed with water and toluene were added and subjected to washing operations. Then silica gel chromatography (toluene / Purification by ethyl acetate = 5/1 (volume ratio)) to give 2,7-dimethoxy-9-(naphthalen-1-yl)-9H-carbazole (12.4 g).
12.4 g With caesium carbonate In dimethyl sulfoxide at 150℃; for 11h; Synthesis of 2,7-dimethoxy-9-(naphthalen-1-yl)-9H-carbazole It was synthesized according to the procedure described in the synthesis known literature 2,7-dimethoxy-9H-carbazole (10g), 1-fluoro-naphthalene (9.7g), Cesium carbonate (17.2g) and dimethyl sulfoxide (150ml) the flask containing, under a nitrogen atmosphere, and the mixture was stirred for 11 hours at 150°C. Thereafter, the reaction solution was cooled to room temperature, the precipitate was filtered off by suction filtration, water and toluene was added, it was subjected to water-washing operation. Then purified by silica gel chromatography (toluene / ethyl acetate = 5/1 (volume ratio)) to give 2,7-dimethoxy-9-(naphthalen-1-yl)-9H-carbazole (12.4 g).
  • 36
  • [ 54147-88-5 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: 4,4′-dimethoxy-2,2′-diaminebiphenyl With tert.-butylnitrite In 1,2-dichloro-ethane for 0.166667h; Sealed tube; Stage #2: With oxygen In 1,2-dichloro-ethane at 20℃; for 24h; Sealed tube; Irradiation;
  • 37
  • [ 1310404-85-3 ]
  • [ 153898-63-6 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 16 h / 120 °C 2.1: tert.-butylnitrite / 1,2-dichloro-ethane / 0.17 h / Sealed tube 2.2: 24 h / 20 °C / Sealed tube; Irradiation
  • 38
  • [ 61822-18-2 ]
  • [ 79-08-3 ]
  • C16H15NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydroxide In dimethyl sulfoxide at 95℃; for 30h; 1 Synthesis of Compound A In a 100 mL flask, 19.0 g (83.6 mmol) of compound 1, 40mL dimethyl sulfoxide, 15.1g (377.5 mmol) of sodium hydroxide and 14.0 g (100.8 mmol) of bromoacetic acid were successively added and reacted at 95° C for 30 h. After completion of the reaction, water was added, suction filtration was carried out to obtain filtrate. The filtrate was adjusted to pH 2 ~ 3, suction filtration was carried out, the filter cake was dried to give 13.8 g of a solid, that is compound 2. The yield was 58.0%.
  • 39
  • [ 61822-18-2 ]
  • [ 67515-59-7 ]
  • 4-(2,7-dimethoxy-9H-carbazol-9-yl)-3-(trifluoromethyl)benzonitrile [ No CAS ]
  • 40
  • [ 92248-06-1 ]
  • [ 61822-18-2 ]
  • C14H13NO2 [ No CAS ]
  • 41
  • [ 61822-18-2 ]
  • 9-(2-chloropyridin-4-yl)-9H-carbazole-2,7-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 72 h / 120 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 1.17 h / 0 °C / Inert atmosphere
  • 42
  • [ 61822-18-2 ]
  • 9-(2-chloropyridin-4-yl)-2,7-bis(hexyloxy)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 72 h / 120 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 1.17 h / 0 °C / Inert atmosphere 3: dimethyl sulfoxide / 2 h / 20 °C
  • 43
  • [ 61822-18-2 ]
  • 3-(4-(2,7-bis(hexyloxy)-9H-carbazol-9-yl)pyridin-2-yl)-2,6-difluorobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 72 h / 120 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 1.17 h / 0 °C / Inert atmosphere 3: dimethyl sulfoxide / 2 h / 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 90 °C / Inert atmosphere
  • 44
  • [ 61822-18-2 ]
  • 9-(2',6'-difluoro-[2,3'-bipyridin]-4-yl)-2,7-bis(hexyloxy)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 72 h / 120 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 1.17 h / 0 °C / Inert atmosphere 3: dimethyl sulfoxide / 2 h / 20 °C 4: potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / 1,4-dioxane; water / 18 h / 60 °C / Inert atmosphere
  • 45
  • [ 153034-86-7 ]
  • [ 61822-18-2 ]
  • 9-(2-chloropyridin-4-yl)-2,7-dimethoxy-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 72h; Inert atmosphere;
  • 46
  • [ 10016-52-1 ]
  • [ 61822-18-2 ]
  • C40H30N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper In nitrobenzene at 210℃; Alkaline conditions;
  • 47
  • [ 1402045-63-9 ]
  • [ 61822-18-2 ]
YieldReaction ConditionsOperation in experiment
44% With phosphoric acid In diethylene glycol at 200℃; for 24h; Acid-Mediated Intramolecular Amination; General Procedure General procedure: In a 10-mL, round-bottom flask, 2,2’-bis(acetamido)biphenyl 2 (0.5 mmol, 1.0 equiv) was dissolved in diethylene glycol (10 mL), followed by addition of phosphoric acid (0.49 g, 5 mmol, 10 equiv). The mix- ture was stirred at 200 °C until completion and cooled to r.t. Organic components were extracted into CH2Cl2 and the combined organic extracts were washed with brine and dried (anhyd MgSO4). Solvents were removed under reduced pressure to obtain the crude product, which was purified by flash chromatography (EtOAc/n-hexane).
  • 48
  • [ 61822-18-2 ]
  • 2-(2-(2-methoxyethoxy)ethoxy)ethyl 5-bromothiophene-2-carboxylate [ No CAS ]
  • 2-(2-(2-methoxyethoxy)ethoxy)ethyl 5-(2,7-dimethoxy-9H-carbazol-9-yl)-2-thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 3h; General procedure for the synthesis of I To a solution of compound 1a (3.52 g, 10 mmol) and 2,7-dimethoxy-9H-carbazole (2.27 g, 10 mmol) in DMF (20 mL)was added CuI (2.46 g, 13 mmol) and K2CO3 (1.65 g, 12 mmol). After the reaction mixture was stirred at 130 °C for 3 h, then was cooled and concentrated under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product. The crude product could be purified by chromatography on silica by elution with a gradient of EtOAC/Petroleum ether (1:4) to obtain compound I[1]. 2-(2-(2-methoxyethoxy)ethoxy)ethyl 5-(2,7-dimethoxy-9H-carbazol-9-yl)-2-thiophene- 2-carboxylate yield 17%. 1H-NMR (CDCl3, 600 MHz) δ 7.93 (d, 1H, J = 6 Hz, C=CH), 7.86 (d, 1H, J = 12 Hz, C=CH), 7.20 (d, 1H,J = 6 Hz, C=CH), 6.98 (d, 2H, J = 1.8 Hz, C=CH), 6.91 (dd, 2H, J =12 Hz, J = 6 Hz, C=CH), 4.51 (t, 2H, J = 4.8 Hz,-CH2-), 3.85 (s, 6H, -OCH3), 3.83 (t, 2H, J = 4.8 Hz, -CH2-), 3.73 (m, 2H, -CH2-), 3.68 (m, 2H, -CH2-), 3.65 (m, 2H, -CH2-), 3.54 (m, 2H, -CH2-), 3.35 (s, 3H, -CH3). 13C-NMR (DMSO-d6, 150 MHz) δ 161.35, 158.72, 144.23, 142.16, 134.13, 130.13, 126.17, 120.95, 117.37, 110.00, 94.89, 71.63, 70.30, 70.12, 69.99, 68.63, 64.90, 58.35, 55.85. HRMS (m/s): calcd for C26H29NO7S [M]+: 499.1659, found: 499.1649.
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 3h; 1 Compound A-1 3.52gAnd 2,7-dimethoxy-9H-carbazole 2.7g dissolved in DMF,Then add cuprous iodide and potassium carbonate,React at 130 for 3h,Then the solvent was removed under reduced pressure,Extract with ethyl acetate,Dry with anhydrous sodium sulfate,Finally, column chromatography purification,Compound B-1 is obtained.
  • 50
  • [ 108-86-1 ]
  • [ 61822-18-2 ]
  • 2,7-dimethoxy-9-phenylcarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper (I) iodide; potassium carbonate at 130℃; for 3h; 13 Synthesis of target compound 9: Take 2,7-dimethoxycarbazole, bromobenzene, cuprous iodide, potassium carbonate in turn, dissolve in xylene, and react at 130 °C for 3 h. The subsequent preparation steps are the same as compound 1 to obtain compound 9.
  • 51
  • [ 61822-18-2 ]
  • [ 54149-17-6 ]
  • C19H23NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 2,7-Dimethoxy-9H-Carbazole With sodium hydride In tetrahydrofuran; kerosene at 50℃; for 0.5h; Stage #2: 2-bromoethyl 2-methoxyethyl ether In tetrahydrofuran; kerosene at 20℃; for 3h; 1 Synthesis of compound A (compound 1 intermediate): Take 2,7-dimethoxycarbazole powder and 60% sodium hydride kerosene mixture, stir in anhydrous tetrahydrofuran at 50°C for 0.5h, then add 1-bromo-2-(2-methoxyethoxy)ethane was reacted at room temperature for 3 h to obtain compound A. It was a brown oily liquid with a yield of 87%.
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