Water → Ethyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907949ノート

反応式

HRID 907949 の反応式
[F:1][C:2]1[CH:19]=[CH:18][C:5](/[CH:6]=[N:7]/[C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2[CH2:10][O:11][C:12]3=[O:17])=[CH:4][CH:3]=1.[CH:20]([C:22]1[CH:32]=[CH:31][C:25]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[CH:24][CH:23]=1)=O.[O-:33][CH2:34][CH3:35].[Na+].O>C(OCC)(=O)CC.CCOC(C)=O>[CH3:29][N:28]([CH3:30])[C:26]([C:25]1[CH:31]=[CH:32][C:22]([CH:20]2[C:34](=[O:33])[C:35]3[C:13]([C:12]([O:11][CH2:10][CH3:9])=[O:17])=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][CH:6]2[C:5]2[CH:18]=[CH:19][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:23][CH:24]=1)=[O:27]

参加物

7

反応物 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 105592054-formyl-N,N-dimethylbenzamideHCID 178519076HCID 178519076、化合物

生成物 1

HCID 67261670Ethyl 3-(4-(dimethylcarbamoyl)phenyl)-2-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate収率 44%

試薬・触媒・溶媒 2

HCID 7749Ethyl Propionate溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
30 °C

実験手順

Sodium (115 mg, 5 mmol) was added to EtOH (10 mL) to afford sodium ethoxide. (E)-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one (500 mg, 1.96 mmol) and 4-formyl-N,N-dimethylbenzamide (382 mg, 2.16 mmol) were dissolved in ethyl propionate (10 mL), and the sodium ethoxide solution was added dropwise to the mixture at 0° C., then the mixture were heated to 30° C. for 1 h. To the reaction mixture was added water and EtOAc, the organic phase was separated, washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and then concentrated to afford the crude product. The crude product was purified by flash chromatography (MeOH:DCM 1:25) to give the title compound (400 mg, yield 44%). LC-MS (ESI) m/z: 461(M+1)+.

後処理

  1. customthe organic phase was separated
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto afford the crude product
  6. customThe crude product was purified by flash chromatography (MeOH:DCM 1:25)

出典と根拠

ORDレコード
ord-39ca926ed09b49d1a052cebabf822a1d
出典データセット
uspto-grants-2011_09
特許番号
US08012976B2

反応ノート

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