Sodium Iodide → methyl 3-(5-cyano-1H-indol-3-yl)propanoate

HRID 1647787노트

반응식

HRID 1647787 반응식
[CH3:1][O:2][C:3]([CH:5]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1)C(OC)=O)=[O:4].[I-].[Na+]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:10][CH2:5][C:3]([O:2][CH3:1])=[O:4])#[N:21]

참가 물질

5

반응물 2

HCID 5238Sodium IodideHCID 19921655methyl 2-methoxycarbonyl-3-(5-cyano-1H-indol-3-yl)propanoate

생성물 1

HCID 19921624methyl 3-(5-cyano-1H-indol-3-yl)propanoate수율 80,799.5%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매

실험 절차

To a solution of 1.14 g (3.98 mmol, 1.0 equiv.) of methyl 2-methoxycarbonyl-3-(5-cyano-1 H-indol-3-yl)propanoate in 20 mL of pyridine was added 1.19 g (7.96 mmol, 2.0 equiv.) of sodium iodide. The mixture was heated to reflux for sixteen hours. The solution was cooled and diluted with 150 mL of chloroform. The organic layer was washed once with 25 mL of saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was filtered through a plug of silica gel with 1:1 ethyl acetate:hexane to remove colored impurities to provide 0,734 g (81%) of methyl 3-(5-cyano-1H-indol-3-yl)propanoate.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for sixteen hours
  3. temperatureThe solution was cooled
  4. washThe organic layer was washed once with 25 mL of saturated aqueous sodium bicarbonate solution
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationThe resulting residue was filtered through a plug of silica gel with 1:1 ethyl acetate
  10. customhexane to remove colored impurities

출처 및 근거

ORD 기록
ord-57118cae55d24259871a053e932212b8
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05434154

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