Acetic Acid → 2-(4-Bromo-2-fluorophenylamino)-6-oxo-1,6-dihydropyridine-3-carboxylic acid
Reaktionsgleichung
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[NH:7][C:6]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[F:20])=[O:4].COC(=O)C1C=CC(OC)=NC=1NC1C=CC(Br)=CC=1F.C(O)(=O)C.Br>CCOC(C)=O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:6]2[NH:7][C:8](=[O:11])[CH:9]=[CH:10][C:5]=2[C:3]([OH:4])=[O:2])=[C:14]([F:20])[CH:15]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 92.5 °C
Versuchsvorschrift
Preparation of 2-(4-bromo-2-fluorophenylamino)-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester: To 2-(4-bromo-2-fluorophenylamino)-6-methoxy-nicotinic acid methyl ester (1.00 g, 2.82 mmol) in a sealed flask was added glacial acetic acid (10 mL) and HBr (10 mL, 48 wt % in H2O). The reaction mixture was stirred at 90-95° C. for 2 hours and then cooled to room temperature. The reaction mixture was diluted with EtOAc and washed with H2O, saturated NaHCO3, and saturated NaCl, dried over Na2SO4 and concentrated under reduced pressure. The crude product was triturated twice with dichloromethane/methanol and the resulting solid was collected and dried under vacuum to yield 0.756 g (79%) pure desired product as a white solid.
Aufarbeitung
- temperaturecooled to room temperature
- washwashed with H2O, saturated NaHCO3, and saturated NaCl
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude product was triturated twice with dichloromethane/methanol
- customthe resulting solid was collected
- customdried under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-6229ce4b27ef4e89829df75a7ac79ab2
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08101611B2
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