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

HRID 408047

反応式

HRID 408047 の反応式
[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

参加物

6

反応物 3

HCID 1230471,2,3-TriazineHCID 2723922Sodium ethoxide2 回HCID 10585213Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

生成物 1

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

試薬・触媒・溶媒 2

HCID 1230471,2,3-Triazine触媒HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-d1178c98ee174d70bc654a2047a0995e
出典データセット
uspto-grants-2014_06
特許番号
US08754230B2

関連ノート

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