Water → Methyl 2-(4-fluorophenoxy)-5-(trifluoromethyl)nicotinate
Reaktionsgleichung
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[N:16]=[CH:15][C:14](I)=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[F:20][C:21]([F:26])([F:25])C([O-])=O.[Na+].O.ClCCl>CN1CCCC1.[Cu]I>[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[N:16]=[CH:15][C:14]([C:21]([F:26])([F:25])[F:20])=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
A mixture of methyl 2-(4-fluorophenoxy)-5-iodonicotinate (step 1, 373 mg, 1.0 mmol), sodium trifluoroacetate (1.36 g, 10 mmol), and copper(I) iodide (960 mg, 5.0 mmol) in 1-methyl-pyrolidine (8.0 mL) was stirred at 160° C. for 16 h under nitrogen atmosphere. The reaction mixture was poured into water (20 mL) and extacted with dichloromethane (50 mL×3). The combined organic extracts were washed with brine (50 mL) and dried (sodium sulfate). After removal of the solvent, the residue was purified by TLC plate developing with hexane/ethyl acetate (1/1) to afford 32 mg (10%) of the title compound: 1H-NMR (CDCl3) δ 8.5 (2H, s), 7.13 (1H, d, J=6.3 Hz), 3.99 (3H, s); MS (ESI) m/z 316 (M+H)+.
Aufarbeitung
- washThe combined organic extracts were washed with brine (50 mL)
- dry with materialdried (sodium sulfate)
- customAfter removal of the solvent
- customthe residue was purified by TLC plate
Quellen und Nachweise
- ORD-Eintrag
- ord-a55c78a6b1394766a7589eb15e6231c3
- Quelldatensatz
- uspto-grants-2007_07
- Patentnummer
- US07238714B2
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