Reaktionsgleichung
Cl[C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][S:10]([O:12][Na])=[O:11].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.O>[CH3:9][S:10]([C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)(=[O:12])=[O:11]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
A mixture of 6-chloropyridin-3-ol (2.00 g, 15.44 mmol), MeSO2Na (2.36 g, 23.16 mmol), CuI (882.16 mg, 4.63 mmol), L-proline (533.28 mg, 4.63 mmol), and K2CO3 (640.19 mg, 4.63 mmol) in DMSO (20 mL) were charged into a microwave tube. The sealed tube was heated at 140° C. for 3 hrs under microwave. After cooling to room temperature, water (100 mL) was added. The mixture was extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give the title compound (1.2 g, 44.8%) as a yellow solid. 1H NMR (Methanol-d4, 400 MHz) δ 8.24 (d, J=2.4 Hz, 1H), 7.94 (d, J=8.4 Hz, 1H), 7.37 (dd, J1=8.8 Hz, J2=2.8 Hz, 1H), 3.15 (s, 3H).
Aufarbeitung
- additionwere charged into a microwave tube
- temperatureAfter cooling to room temperature
- extractionThe mixture was extracted with EtOAc (100 mL×3)
- washThe combined organic layers were washed with brine (100 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-11b931590f4240538a587e6d7b16418c
- Quelldatensatz
- uspto-grants-2015_08
- Patentnummer
- US09115114B2
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