StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Water → 3-(1,4-Diisopropyl-6-methyl-1,2,3,4-tetrahydro-7-quinoxalinyl)-4-methoxybenzaldehyde

HRID 488819
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 488819
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]([CH:15]([CH3:17])[CH3:16])[CH2:7][CH2:8][N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[CH3:18].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH3:18])=[C:2]([C:22]3[CH:23]=[C:24]([CH:25]=[CH:26][C:21]=3[O:20][CH3:19])[CH:27]=[O:28])[CH:11]=2)[N:6]([CH:15]([CH3:17])[CH3:16])[CH2:7][CH2:8]1)([CH3:14])[CH3:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 222683017-Bromo-1,4-diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxaline

Produkt 1

HCID 222683433-(1,4-Diisopropyl-6-methyl-1,2,3,4-tetrahydro-7-quinoxalinyl)-4-methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 7-bromo-1,4-diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxaline (469 mg, 1.51 mmol), 2-methoxy-5-formylphenylboronic acid (407 mg, 2.26 mmol), potassium carbonate (834 mg, 6.03 mmol) and water (2.5 mL) in anhydrous 1,2-dimethoxyethane (30 mL) was degassed with argon for 15 minutes prior to the addition of tetrakis(triphenylphosphine)palladium (0) (349 mg, 0.30 mmol). The reaction mixture was heated under reflux for 8.5 hours, allowed to cool to room temperature and extracted with ethyl acetate (2×100 mL). The organic extracts were successively washed with water (100 mL), saturated aqueous NH4Cl (100 mL), saturated aqueous NaCl (100 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave an oil which was purified by column chromatography, using a Biotage 40S cartridge, eluting with 10% ethyl acetate/90% hexane. The title compound was isolated as bright yellow solid (315 mg, 57%).

Aufarbeitung

  1. customwas degassed with argon for 15 minutes
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 8.5 hours
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washThe organic extracts were successively washed with water (100 mL), saturated aqueous NH4Cl (100 mL), saturated aqueous NaCl (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customRemoval of the solvent under reduced pressure
  9. customgave an oil which
  10. customwas purified by column chromatography
  11. washeluting with 10% ethyl acetate/90% hexane

Quellen und Nachweise

ORD-Eintrag
ord-8c7b368876644e1d9de9d4b20aac2b9d
Quelldatensatz
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06974826B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion