Isobutyl iodide → (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isobutyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898240
[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:23])[CH:10]=2)[NH:5][C:4]1=[O:24])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+].I[CH2:38][CH:39]([CH3:41])[CH3:40]>C(#N)C>[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:23])[CH:10]=2)[N:5]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:4]1=[O:24])[CH3:2]

Komponenten

6

Edukt 4

HCID 10556Isobutyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 69223657(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Produkt 1

HCID 69223598(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isobutyl-3,4-dihydroquinoxalin-2(1H)-oneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
74 °C

Versuchsvorschrift

To a stirred solution of (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (see Example 8) (0.25 g, 0.76 mmol) in acetonitrile (6 mL) under nitrogen was added cesium carbonate (0.13 g, 0.40 mmol), potassium carbonate (0.055 g, 0.40 mmol) and 1-iodo-2-methylpropane (0.30 mL, 0.48 g, 2.6 mmol). The mixture was stirred at 74° C. for 12 h. The solvent was then evaporated, and the residue was partitioned between methylene chloride and water. The organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated in vacuo. The product was purified via Biotage Horizon® (SiO2, gradient from 4% EtOAc/hexane to 38% EtOAc/hexane) to yield 0.10 g (35%) of (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-1-isobutyl-3,4-dihydroquinoxalin-2(1H)-one.

Aufarbeitung

  1. customThe solvent was then evaporated
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe product was purified via Biotage Horizon® (SiO2, gradient from 4% EtOAc/hexane to 38% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2483fd9fc51e49288c66c4fbe821b533
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351709B2

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