Methyl iodide → 7-Methoxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one

HRID 1783660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783660
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:15])[CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.[C:17]([O-])([O-])=O.[K+].[K+].CI>C1COCC1>[CH3:17][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:14])[CH3:15])[C:9]2=[O:12])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1363729927-Hydroxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one

Produkt 1

HCID 211065847-Methoxy-2-Isopropyl-4-bromo-2H-phthalazin-1-oneAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 7-hydroxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one (0.4 g, 1.4 mmol) in THF (5 ml) were added successively, K2CO3 (0.59 g, 4.3 mmol) and methyl iodide (0.22 g, 1.55 mmol) and the mixture was heated to reflux for 24 hours. After this time, LC-MS indicated complete consumption of starting material, and the reaction mixture was concentrated under vacuum. The residue was re-dissolved in EtOAc (50 ml) and washed with water (2×30 ml), the organic layer was dried (MgSO4), filtered and concentrated under vacuum to give the title compound (0.32 g, 76% yield) as an orange powder.

Aufarbeitung

  1. temperatureto reflux for 24 hours
  2. customconsumption of starting material
  3. concentrationthe reaction mixture was concentrated under vacuum
  4. dissolutionThe residue was re-dissolved in EtOAc (50 ml)
  5. washwashed with water (2×30 ml)
  6. dry with materialthe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9c3d5b01b17f4236980893f85881ff76
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501410B2

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