Iodoethane → (3R)-4-(2,4-dimethoxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[NH:10][C:9](=[O:18])[C@H:8]1[CH2:19][CH3:20])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:34][CH3:35]>C(#N)C>[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[N:10]([CH2:34][CH3:35])[C:9](=[O:18])[C@H:8]1[CH2:19][CH3:20])=[O:6]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 89 °C
Versuchsvorschrift
To a stirred solution of (3R)-4-(2,4-dimethoxybenzoyl)-3-ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one (0.25 g, 0.73 mmol) in acetonitrile (6 mL) under nitrogen was added cesium carbonate (0.24 g, 0.74 mmol) and iodoethane (0.19 mL, 0.37 g, 2.4 mmol). The mixture was stirred at 89° C. in a sealed tube for 12 h. The solvent was evaporated, and the residue was partitioned between water and methylene chloride. The layers were separated, and the organic layer was washed twice with water, dried over magnesium sulfate, concentrated in vacuo, and purified via Biotage Horizon® (SiO2, gradient from 7% EtOAc/hexane to 51% EtOAc/hexane) to yield 0.20 g (71%) of (3R)-4-(2,4-dimethoxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one.
Aufarbeitung
- customThe solvent was evaporated
- customthe residue was partitioned between water and methylene chloride
- customThe layers were separated
- washthe organic layer was washed twice with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- custompurified via Biotage Horizon® (SiO2, gradient from 7% EtOAc/hexane to 51% EtOAc/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-25493bf928c44efcaf7312b16f6447e8
- Quelldatensatz
- uspto-grants-2008_04
- Patentnummer
- US07351709B2
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