Potassium Carbonate → Benzyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

HRID 56868

反応式

HRID 56868 の反応式
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]2[C:21]([O:22][CH3:23])=[CH:20][NH:19][C:18](=[O:24])[CH:17]=2)[CH:9]=1.Br[CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].[Cl-].[Li+]>CN(C)C=O.O>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]2[C:21]([O:22][CH3:23])=[CH:20][N:19]([CH2:26][C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])[C:18](=[O:24])[CH:17]=2)[CH:9]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 433294Lithium ChlorideHCID 1176049354-Chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile

生成物 1

HCID 117622981Benzyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

3.18 g (23.0 mmol) of potassium carbonate were added to a solution of 4.00 g (15.3 mmol) of 4-chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile and 2.92 ml (18.4 mmol) of benzyl bromoacetate in 53.3 ml of dimethylformamide, and the mixture was then stirred at 100° C. for 45 min. The reaction mixture was cooled to RT and the reaction was ended by adding 530 ml of water and 10.0 g (236 mmol) of lithium chloride. The mixture was extracted three times with 200 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The residue was dissolved in 50 ml of dichloromethane, applied to diatomaceous earth and purified by flash chromatography (120 g cartridge, 80 ml/min, ethyl acetate/cyclohexane gradient). Yield: 3.90 g (61% of theory)

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe mixture was extracted three times with 200 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe residue was dissolved in 50 ml of dichloromethane
  7. custompurified by flash chromatography (120 g cartridge, 80 ml/min, ethyl acetate/cyclohexane gradient)

出典と根拠

ORDレコード
ord-ee94b06db5ee4be4aeede6faed6236f7
出典データセット
uspto-grants-2016_09
特許番号
US09434690B2

関連ノート

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