1,2,3-Triazine → Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

HRID 408047

Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[CH3:17]C[O-].[Na+].[N:21]1[CH:26]=CC=NN=1>CCO.N1C=CC=NN=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:16])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:17][NH:21][CH:26]=2)=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

To a solution of ethyl 4-(4-fluorophenyl)-3-oxobutanoate (4.6 g, 21 mmol) in absolute EtOH (45 mL) was added NaOEt solution (21% NaOEt solution in EtOH, 7.7 mL) and triazine (1.67 g, 21 mmol). The resulting mixture was heated to 85° C. for 1.5 h, cooled to room temperature and treated with an additional portion of triazine (0.08 g, 1 mmol) and NaOEt solution (21% NaOEt solution in EtOH, 0.4 mL). The reaction mixture was heated for an additional hour and concentrated in vacuo. The residue was treated with 1N HCl until the pH of the reaction was about 2. The precipitate was collected to give the desired ester intermediate, ethyl 5-(4-fluorophenyl )-4-oxo-1,4-dihydropyridine-3-carboxylate (4.5 g, 83%) as a yellow solid. MS (ESI+) m/z 262 (M+H)+.

Aufarbeitung

temperaturecooled to room temperature
temperatureThe reaction mixture was heated for an additional hour
concentrationconcentrated in vacuo
additionThe residue was treated with 1N HCl until the pH of the reaction
customThe precipitate was collected

Quellen und Nachweise

ORD-Eintrag: ord-d1178c98ee174d70bc654a2047a0995e
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08754230B2

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