Cesium carbonate → HCID 68699922, Verbindung
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][CH2:12][CH3:13])[CH:5]=1.[F:15][C:16]([F:20])([F:19])[CH2:17]I.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([O:10][CH2:17][C:16]([F:20])([F:19])[F:15])[CH:7]=[C:6]([O:11][CH2:12][CH3:13])[CH:5]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 130 °C
Versuchsvorschrift
A mixture of 3-ethoxy-5-hydroxy-benzoic acid methyl ester (1.5 g, 7.65 mmol, 1.0 equiv; prepared as described in WO 99/05123 A1, Astra Pharmaceuticals Ltd.), 2,2,2-trifluoroethyl iodide (2.25 mL, 4.82 g, 22.94 mmol, 3.0 equiv) and cesium carbonate (4.98 g, 15.29 mmol, 2.0 equiv) was heated to 130° C. under microwave irradiation for 20 min. The crude reaction mixture was filtered over Hyflo Super Cel and extracted with dichloromethane (3×50 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified by flash column chromatography on silica eluting with a gradient of heptane/dichloromethane (1:1→0:1) yielding 0.89 g (42%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.35 (t, J=7.0 Hz, 3H), 3.84 (s, 3H), 4.00 (q, J=7.0 Hz, 2H), 4.30 (q, J=8.1 Hz, 2H), 6.62-6.63 (m, 1H), 7.10-7.11 (m, 1H), 7.19-7.21 (m, 1H). MS (ISP): 279.0 [M+H]+.
Aufarbeitung
- customThe crude reaction mixture
- filtrationwas filtered over Hyflo Super Cel
- extractionextracted with dichloromethane (3×50 mL)
- dry with materialThe combined organic phases were dried over MgSO4
- customthe solvent removed by evaporation under reduced pressure
- customthe crude material purified by flash column chromatography on silica eluting with a gradient of heptane/dichloromethane (1:1→0:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-fea9bde581e84dd1a48f522a208e135e
- Quelldatensatz
- uspto-grants-2010_01
- Patentnummer
- US07645753B2
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