Water → 5-Bromo-1,3-dimethoxyisoquinoline

HRID 2090059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090059
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5](Cl)[N:6]=[C:7]2[O:12][CH3:13].[CH3:15][O-:16].[Na+].O>CS(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([O:16][CH3:15])[N:6]=[C:7]2[O:12][CH3:13]

Komponenten

5

Edukt 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 583494645-Bromo-3-chloro-1-methoxyisoquinoline

Produkt 1

HCID 673101605-Bromo-1,3-dimethoxyisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 5-bromo-3-chloro-1-methoxyisoquinoline (420 mg, 1.54 mmol) in DMSO (4.0 mL) was added NaOMe (0.5 M in MeOH, 4.0 mL, 2.0 mmol). The solution was heated at 90° C. for 1.5 hours in a microwave reactor. The mixture was poured into water then extracted with EtOAc. The organics were dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 15% EtOAc/hexanes to afford the title compound: 1H NMR (500 MHz, CDCl3): δ 8.15 (d, J=8.5 Hz, 1H), 7.87 (d, J=8.0 Hz, 1H); 7.18 (t, J=8.0 Hz, 1H), 6.85 (s, 11-1), 4.18 (s, 3H), 4.05 (s, 3H). LC6: 3.67 min, (M+H): 268.

Aufarbeitung

  1. extractionthen extracted with EtOAc
  2. dry with materialThe organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 15% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bc7939f2630c4804a079cb4ee3aa3582
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436015B2

Notizen zur Reaktion

Wird geladen…