Iodoethane → (3R)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 898229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898229
[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-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:38][CH3:39]>C(#N)C>[CH2:38]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([F:23])=[CH:8][CH:7]=2)[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@H:3]([CH2:1][CH3:2])[C:4]1=[O:24])[CH3:39]

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 69223657(3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Produkt 1

HCID 69221429(3R)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of (3R)-3-ethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (0.20 g, 0.61 mmol) in acetonitrile (5 mL) under nitrogen was added potassium carbonate (0.050 g, 0.36 mmol), cesium carbonate (0.11 g, 0.33 mmol) and iodoethane (0.15 mL, 0.29 g, 1.9 mmol). The reaction was stirred for 10 h at 50° C. and then 5 h at 63° C. The solvent was evaporated, and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with water. The organic layer was concentrated in vacuo and purified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 33% EtOAc/hexane) to yield 0.21 g (96%) of (3R)-1,3-diethyl-6-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one. MS (ESI) m/z 357 ([M+H]+); HRMS: calcd for C20H21FN2O3, 356.16090; found (ESI+), 357.16057.

Aufarbeitung

  1. custom5 h
  2. customat 63° C
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe layers were separated
  6. washthe organic layer was washed with water
  7. concentrationThe organic layer was concentrated in vacuo
  8. custompurified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 33% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-dbf43c6a8c704971853871ea2f93ad39
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351709B2

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