Methyl iodide → 7-Bromo-8-methoxycarbonyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871971
[Br:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([NH:6][C:7]([CH3:18])([CH3:17])[C:8](=[O:16])[NH:9]2)=[CH:4][CH:3]=1.CI.[C:21](=O)([O-])[O-].C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([NH:6][C:7]([CH3:18])([CH3:17])[C:8](=[O:16])[N:9]2[CH3:21])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 19660Carbonate IonHCID 24780709Methyl 6-bromo-2,2-dimethyl-3-oxo-1,2,3,4-tetrahydroquinoxaline-5-carboxylate

Produkt 1

HCID 247809997-Bromo-8-methoxycarbonyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 7-bromo-8-methoxycarbonyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 1, 102 mg, 0.326 mmol), methyl iodide (100 μL, 1.60 mmol), and cessium carbonate (272 mg, 0.835 mmol) was suspended in anhydrous N,N-dimethylformamide (5 mL) and stirred at room temperature for 2 hours. Ethyl acetate (25 mL) and water (25 mL) were added to the reaction mixture and partitioned. The organic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (86.0 mg) as a pale yellow solid. (Yield 83%)

Aufarbeitung

  1. custompartitioned
  2. washThe organic layer was washed with saturated brine (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c62c558434d7461cbea364946de475a3
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975256B2

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