Ammonium formate → HCID 21462997, compound

HRID 1940552Notes

Reaction equation

HRID 1940552 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>CO.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54142756HCID 54142756, compound

Product 1

HCID 21462997HCID 21462997, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(pyridin-4-yl)-2-(furan-2-yl)ethene (8 g, 46.8 mmol) in methanol (200 ml) was treated with ammonium formate (14.7 g, 234.0 mmol). 10% Palladium on charcoal catalyst (400 mg, 5% (w/w)) was added and the mixture was stirred at reflux for five hours. The catalyst was filtered off and the solvent evaporated. The residue was partitioned between dichloromethane and water. The organic layer was separated, dried (MgSO4) and evaporated to give a beige oil. This material was chromatographed on silica gel with a gradient of ethyl acetate in hexane (50%-100%) as eluant to afford the title compound as a colourless oil (2.5 g, 31%); δH (DMSO-d6) 2.94-3.06 (4H, m, 2×CH2), 6.06-6.12 (1H, m, furanyl H), 6.32-6.38 (1H, m, furanyl H), 7.20-7.28 (2H, m, pyridinyl H), 7.50-7.56 (1H, m, furanyl H), and 8.40-8.50 (2H, m, pyridinyl H).

Workup

  1. temperatureat reflux for five hours
  2. filtrationThe catalyst was filtered off
  3. customthe solvent evaporated
  4. customThe residue was partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a beige oil
  9. customThis material was chromatographed on silica gel with a gradient of ethyl acetate in hexane (50%-100%) as eluant

Sources & evidence

ORD record
ord-c27bdad2c0de44bf9577e1cfb586530b
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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