1,2-Diaminocyclohexane, trans- → 9-(2'-nitrobiphenyl-4-yl)-2-(pyridin-2-yl)-9H-carbazole

HRID 1509634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509634
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=1.I[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[N+:33]([O-:35])=[O:34])=[CH:23][CH:22]=1.[C@@H]1(N)CCCC[C@H]1N.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>ClCCl.CO.[Cu]I>[N+:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([N:10]2[C:9]3[CH:8]=[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:26][CH:25]=1)([O-:35])=[O:34]

Komponenten

7

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 6297494'-Iodo-2-nitrobiphenylHCID 222472152-(2-pyridyl)-9H-carbazole

Produkt 1

HCID 1181139679-(2'-nitrobiphenyl-4-yl)-2-(pyridin-2-yl)-9H-carbazoleAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
112.5 °C

Versuchsvorschrift

2-(Pyridin-2-yl)-9H-carbazole (611 mg, 2.5 mmol, 1.0 eq), 4′-iodo-2-nitrobiphenyl (975 mg, 3.0 mmol, 1.2 eq), CuI (48 mg, 0.25 mmol, 0.1 eq), trans-cyclohexane-1,2-diamine (250 uL, 2.5 mmol, 1.0 eq) and K3PO4 (1114 mg, 5.25 mmol, 2.1 eq) were added to a dry pressure vessel equipped with a magnetic stir bar. The vessel was evacuated and back-filled with nitrogen. The evacuation and back-fill procedure was repeated twice. Then solvent dioxane (10 mL) was added under nitrogen. After bubbling with nitrogen for 30 minutes, the mixture was stirred at 110-115° C. in an oil bath for 4 days. Then the mixture was cooled to ambient temperature. The solvent was removed under reduced pressure and the residue was purified through column chromatography on silica gel using hexane/ethyl acetate (10:1-3:1) then dichloromethane/methanol (20:1) as an eluent to obtain the desired product as a solid (1.04 g in 94% yield). 1H NMR (DMSO-d6, 400 MHz): δ 7.36 (t, J=6.0 Hz, 2H), 7.45 (d, J=8.0 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.70-7.92 (m, 8H), 8.05 (t, J=8.4 Hz, 2H), 8.10 (d, J=8.4 Hz, 1H), 8.22 (s, 1H), 8.33 (d, J=7.2 Hz, 1H), 8.39 (d, J=8.0 Hz, 1H), 8.67 (d, J=4.8 Hz, 1H).

Aufarbeitung

  1. customequipped with a magnetic stir bar
  2. customThe vessel was evacuated
  3. additionback-filled with nitrogen
  4. additionThen solvent dioxane (10 mL) was added under nitrogen
  5. customAfter bubbling with nitrogen for 30 minutes
  6. temperatureThen the mixture was cooled to ambient temperature
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified through column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f7a48549f2024f938bc1b880bdb3b337
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09224963B2

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