Sodium Hydroxide → HCID 58437451, compound

HRID 881638Notes

Reaction equation

HRID 881638 reaction equation
[CH:1]([C:3]1[O:7][C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]#[N:18])=[CH:9]2)=[CH:5][CH:4]=1)=[O:2].[OH-:19].[Na+]>CO.O1CCCC1.[Ag]=O>[C:17]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:6]2[O:7][C:3]([C:1]([OH:19])=[O:2])=[CH:4][CH:5]=2)[CH:9]=1)#[N:18]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 584373031-(5-Formylfuran-2-yl)-1H-indole-3-carbonitrile

Product 1

HCID 58437451HCID 58437451, compound

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(5-formylfuran-2-yl)-1H-indole-3-carbonitrile (0.085 g) in methanol (4 mL) and tetrahydrofuran. (4 mL) were added silver oxide (0.1 g) and 2 mol/L aqueous sodium hydroxide solution (0.27 mL), this mixture was stirred at room temperature for 6 hours. The insoluble material of reaction mixture was removed by filtration, and the filtrate was concentrated under reduced pressure. To this residue were added water (15 mL) and 2 mol/L hydrochloric acid solution (2 mL), this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.023 g).

Workup

  1. customThe insoluble material of reaction mixture
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo this residue were added water (15 mL) and 2 mol/L hydrochloric acid solution (2 mL)
  5. extractionthis mixture was extracted with ethyl acetate
  6. washThis organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-f6ebe9e6ed6d4b6cafb898b93d030a83
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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