Ammonium formate → HCID 21463007, compound

HRID 1940556Notes

Reaction equation

HRID 1940556 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]>[O:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[CH2:8][CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54142756HCID 54142756, compound

Product 1

HCID 21463007HCID 21463007, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(pyridin-4-yl)-2-(furan-2-yl)ethene (15.0 g, 87.7 mmol) [Example 18, Step 1] in methanol (300 ml) was treated with ammonium formate (27.6 g, 438.5 mmol) and 10% palladium on charcoal catalyst (1.5 g, 10% (w/w)). The mixture was stirred at reflux for 3 hours. The catalyst was removed by filtration and the solvent was evaporated in vacuo. The residue was partitioned between dichloromethane and water. The organic phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed with 1:1 hexane/ethyl acetate as eluant to afford the title compound as a colourless oil (3.0 g, 19%); δH (DMSO-d6) 1.35-1.50 (1H, m, tetrahydrofuranyl H), 1.70-2.00 (5H, m, CH2 and 3×tetrahydrofuranyl H), 2.54-2.76 (2H, m, CH2), 3.54-3.82 (3H, m, tetrahydrofuranyl H), 7.22 (2H, d, J 7.1 Hz, ArH), and 8.46 (2H, d J 7.0 Hz, ArH); m/z (CI+, NH3) 178 (M+1)+.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was partitioned between dichloromethane and water
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was chromatographed with 1:1 hexane/ethyl acetate as eluant

Sources & evidence

ORD record
ord-03783a03ad3440de88508358eaf489fa
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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