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

HRID 2380949Notes

Reaction equation

[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>C(O)C.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

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of ethyl 4-(4-fluorophenyl)-3-oxobutanoate (4.6 g, 21 mmol) in absolute ethanol (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)+.

Workup

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

Sources & evidence

ORD record: ord-b8a2fb99d73f4abc832ef25d4d641f88
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258118B2

Reaction notes

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