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

HRID 408047

반응식

HRID 408047 반응식
[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

참가 물질

6

반응물 3

HCID 1230471,2,3-TriazineHCID 2723922Sodium ethoxide2회HCID 10585213Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

생성물 1

HCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate수율 83%

시약·촉매·용매 2

HCID 1230471,2,3-Triazine촉매HCID 702Ethanol용매

반응 조건

온도
85 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-d1178c98ee174d70bc654a2047a0995e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754230B2

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