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

HRID 1463335ノート

反応式

HRID 1463335 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 19921624methyl 3-(5-cyano-1H-indol-3-yl)propanoate収率 81%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒

実験手順

To a solution of 1.14 g (3.98 mmol, 1.0 equiv.) of methyl 2-methoxycarbonyl-3-(5-cyano-1H-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.

後処理

  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

出典と根拠

ORDレコード
ord-235d7eb6a5f743888cb19633f805efd9
出典データセット
uspto-grants-1994_04
特許番号
US05300506

反応ノート

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