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Hydrochloric Acid → HCID 178487105, Verbindung

HRID 2400283
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2400283
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[N:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][CH:14]=1)[C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:6]2.C(O)(C)C.[N-:31]=[N+:32]=[N-:33].[Na+].Cl>C(OCC)(=O)C.[Br-].[Zn+2].[Br-].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([C:19]3[NH:33][N:32]=[N:31][N:20]=3)[N:18]=1)[C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:6]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 33557Sodium AzideHCID 867079356-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile

Produkt 1

HCID 178487105HCID 178487105, VerbindungAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10421208
Zinc bromide
Katalysator
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile (95 mg), isopropyl alcohol (6 mL), and water (4 mL) were added sodium azide (36 mg) and zinc bromide (32 mg). This mixture was stirred overnight while heated to reflux. The reaction mixture was left to cool to room temperature, and then diluted with ethyl acetate. To the mixture was added 2 mol/L hydrochloric acid (4 mL), followed by stirring at room temperature for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol) to obtain the title compound (88 mg). 1H-NMR (DMSO-d6) δ ppm: 3.78 (3H, s), 5.61 (2H, s), 6.54 (1H, d, J=7.8 Hz), 6.66 (1H, d, J=0.4 Hz), 6.78 (1H, dd, J=2.5, 8.9 Hz), 7.16 (1H, d, J=2.5 Hz), 7.29 (1H, d, J=8.9 Hz), 7.35-7.55 (5H, m), 7.90 (1H, t, J=7.8 Hz), 8.05 (1H, d, J=7.8 Hz). ESI-MS (m/z): 383 (M+H)+

Aufarbeitung

  1. temperaturewhile heated to reflux
  2. waitThe reaction mixture was left
  3. stirringby stirring at room temperature for 30 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-e5271f95b21947ae86ed22d13bad322d
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08796247B2

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