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

HRID 1647787Notes

Reaction equation

HRID 1647787 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-57118cae55d24259871a053e932212b8
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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