Water → (E)-3-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-N-methoxy-N-methylacrylamide

HRID 352099

反応式

HRID 352099 の反応式
[H-].[Na+].CCOP(OCC)([CH2:8][C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])=O.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH:34]([CH3:36])[CH3:35])[C:26]=2[CH:37]=O)=[CH:21][CH:20]=1.O>C1COCC1>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH:34]([CH3:35])[CH3:36])[C:26]=2/[CH:37]=[CH:8]/[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2773719Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonateHCID 113120613-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole-2-carbaldehyde

生成物 1

HCID 22715057(E)-3-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-N-methoxy-N-methylacrylamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

0.465 g (10.65 mmol) of sodium hydride (55%) are introduced into a 100 ml three-necked, round-bottomed flask, equipped with a magnetic stirrer, thermometer, dropping funnel and nitrogen delivery line, and washed twice with 5 ml of pentane. The pentane is removed using a pipette and the sodium hydride is blown dry with nitrogen. 10 ml of THF, rendered absolute using sodium, are added, and 1.84 g (7.46 mmol) of diethyl (N-methoxy-N-methylcarbamoyl-methyl)phosphonate dissolved in 5 ml of THF are slowly added dropwise so that the temperature does not exceed 30° C. 1 g (3.55 mmol) of 3-(4-fluorophenyl)-1-isopropyl-1H-indole-2-carbaldehyde dissolved in 10 ml of THF is then added dropwise and the clear, slightly yellow solution is stirred overnight. The reaction mixture is poured into 100 ml of water and extracted 3 times with 50 ml of ethyl acetate. The combined organic phases are washed twice with 50 ml of saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated by evaporation. Flash chromatography (hexane/ethyl acetate=2:1) and crystallisation from 94% ethanol yields slightly yellow crystals having a melting point of from 123 to 124° C.

後処理

  1. customround-bottomed flask, equipped with a magnetic stirrer
  2. washnitrogen delivery line, and washed twice with 5 ml of pentane
  3. customThe pentane is removed
  4. dry with materialthe sodium hydride is blown dry with nitrogen
  5. additionare added
  6. additionare slowly added dropwise so that the temperature
  7. customdoes not exceed 30° C
  8. additionis then added dropwise
  9. extractionextracted 3 times with 50 ml of ethyl acetate
  10. washThe combined organic phases are washed twice with 50 ml of saturated sodium chloride solution
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated by evaporation
  14. customFlash chromatography (hexane/ethyl acetate=2:1) and crystallisation from 94% ethanol
  15. customyields slightly yellow crystals
  16. customof from 123 to 124° C.

出典と根拠

ORDレコード
ord-656e2e99dbce4133acb6ccb2fabcd19b
出典データセット
uspto-grants-2004_06
特許番号
US06743926B2

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