Water → 1-(5-Formylfuran-2-yl)-1H-indole-3-carbonitrile

HRID 1674579Notes

Reaction equation

HRID 1674579 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1)#[N:2].Br[C:13]1[O:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH:18]([C:16]1[O:17][C:13]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]([C:1]#[N:2])=[CH:4]2)=[CH:14][CH:15]=1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2302823-CyanoindoleHCID 6003285-Bromofuran-2-carbaldehyde

Product 1

HCID 584373031-(5-Formylfuran-2-yl)-1H-indole-3-carbonitrileYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-cyanoindole (0.14 g), 5-bromo-2-furaldehyde (0.18 g), and cesium carbonate (0.39 g) in N,N-dimethylformamide (3 mL) was stirred at room temperature or 3 hours. This reaction mixture was heated at 50° C., stirred for 2 hours. After cooling to ambient, water was added to this reaction mixture. This mixture was extracted with ethyl acetate, and this organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1) to give the title compound (0.086 g).

Workup

  1. temperatureThis reaction mixture was heated at 50° C.
  2. stirringstirred for 2 hours
  3. additionwas added to this reaction mixture
  4. extractionThis mixture was extracted with ethyl acetate
  5. washthis organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-0f4c9c1bc0aa4810b4b607a181120bc7
Source dataset
uspto-grants-2011_08
Patent number
US08003647B2

Reaction notes

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