Ethanol → ethyl 5-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-3-fluoropyridine-2-carboxylate
Reaktionsgleichung
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[CH:4][C:3]=1[F:20].C(N(CC)CC)C.[CH2:28]([OH:30])[CH3:29].CN([CH:34]=[O:35])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[C:15]([O:14][C:13]([NH:12][C@@H:10]([CH3:11])[CH2:9][O:8][C:5]1[CH:4]=[C:3]([F:20])[C:2]([C:34]([O:30][CH2:28][CH3:29])=[O:35])=[N:7][CH:6]=1)=[O:19])([CH3:18])([CH3:17])[CH3:16]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Under a carbon monoxide atmosphere, a mixture of tert-butyl {(1S)-2-[(6-chloro-5-fluoropyridin-3-yl)oxy]-1-methylethyl}carbamate (500 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (135 mg), triethylamine (0.229 mL), ethanol (5 mL) and DMF (5 mL) was stirred at 80° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (402 mg).
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate
- washThe combined organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-10c0a04ef7084f16998ced29b0ee4f0e
- Quelldatensatz
- uspto-grants-2014_05
- Patentnummer
- US08729102B2
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