Dimethylformamide → 6-Bromo-3-methoxyisoquinoline

HRID 537188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537188
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([OH:12])=[CH:5]2.[CH3:13]N(C)C=O.CI>CO.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([O:12][CH3:13])=[CH:5]2

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 178515305HCID 178515305, Verbindung

Produkt 1

HCID 674918076-Bromo-3-methoxyisoquinolineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 6-bromoisoquinolin-3-ol (606 mg, 2.70 mmol), silver carbonate (1.5 g, 5.3 mmol), and N,N-dimethylformamide (12 mL) was stirred at room temperature for 16 minutes. Methyl iodide (186 μL, 2.97 mmol) was added and the reaction was left stirring for 18 hours. The reaction was diluted with methanol and filtered through Celite. The filtrate was concentrated and purified by flash column chromatography to give the title compound (90 mg, 14%). +ESI (M+H+1) 240.0; 1H NMR (400 MHz, CDCl3, δ): 8.91 (s, 1H), 7.86 (d, J=1.8 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.43 (dd, J=8.8, 1.8 Hz, 1H), 6.90 (s, 1H), 4.02 (s, 3H).

Aufarbeitung

  1. waitthe reaction was left
  2. stirringstirring for 18 hours
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-61986a3b268e42caa8bbcfa328359dbc
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859773B2

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