5-Bromo-3-methylisoquinoline → 5-Allyl-3-methylisoquinoline

HRID 887238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887238
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9](Br)[CH:8]=[CH:7][CH:6]=2.[CH2:13]([CH:17]([Sn])C=C(CCCC)CCCC)[CH2:14]CC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:17]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([CH3:1])[N:3]=[CH:4]2)[CH:13]=[CH2:14]

Komponenten

5

Edukt 2

HCID 218161685-Bromo-3-methylisoquinolineHCID 86589045Tributylallyltin

Produkt 1

HCID 223376835-Allyl-3-methylisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Methyl-5-bromoisoquinoline (1.0 g, 4.5 mmol), tributylallyltin (1.6 mL, 5.0 mmol), and dichlrobis(tri-o-tolylphosphine)palladium (II) were combined in toluene (100 mL) and refluxed for 14 hours. The mixture was cooled, diluted with ethyl acetate, and washed twice with aqueous NH4Cl. The organic phase was separated, concentrated, and the residue was purified by chromatography (ethyl acetate:hexanes, 30:70) to provide the title compound. 1H NMR (300 MHz, d6-DMSO) 9.21 (s, 1H), 8.00 (d, 1H), 7.63 (m, 2H), 7.58 (m, 1H), 4.18 (s, 2H), 3.62 (s, 3H), 2.62 (s, 3H). MS (DCI/NH3) m/e 216 (M+H)+.

Aufarbeitung

  1. temperaturerefluxed for 14 hours
  2. temperatureThe mixture was cooled
  3. washwashed twice with aqueous NH4Cl
  4. customThe organic phase was separated
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography (ethyl acetate:hexanes, 30:70)

Quellen und Nachweise

ORD-Eintrag
ord-5bbc083c68954457ae6cf5594e4cebae
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247413B2

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