Cesium carbonate → Ethyl 2-[3-(ethylsulfanyl)phenoxy]-5-fluoronicotinate
Reaktionsgleichung
Cl[C:2]1[N:12]=[CH:11][C:10]([F:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:14]([S:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH2:7]([O:6][C:4](=[O:5])[C:3]1[CH:9]=[C:10]([F:13])[CH:11]=[N:12][C:2]=1[O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([S:16][CH2:14][CH3:15])[CH:18]=1)[CH3:8]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Ethyl 2-chloro-5-fluoro-nicotinate (J. Med. Chem. 1993, 36, 2676, M. Winn et. al.) (5.0 g, 24 mmol), 3-ethylsulfanylphenol (3.8 g, 24 mmol) and caesium carbonate (7.98 g, 24 mmol) were suspended in dioxan (50 ml) and the reaction was heated to 100° C. and stirred at this temperature under nitrogen for 8 h. The reaction was cooled to room temperature, filtered and the solid washed with ethyl acetate (50 ml). The filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel eluting with cyclohexane:ethyl acetate (95:5) to give 5-fluoro-2-(3-ethylsulfanyl-phenoxy)-nicotinic acid ethyl ester (1.16 g).
Aufarbeitung
- temperatureThe reaction was cooled to room temperature
- filtrationfiltered
- washthe solid washed with ethyl acetate (50 ml)
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by flash column chromatography on silica gel eluting with cyclohexane:ethyl acetate (95:5)
Quellen und Nachweise
- ORD-Eintrag
- ord-2a1db452f43a4da3b881fa7b3b936d8a
- Quelldatensatz
- uspto-grants-2006_11
- Patentnummer
- US07141586B2
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