Ammonium formate → HCID 54117983, compound

HRID 850114Notes

Reaction equation

HRID 850114 reaction equation
[CH3:1][N:2]([C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[CH2:30])[C:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])([OH:21])[CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:9][CH:8]=1)=[O:6])[O:3][CH3:4].C([O-])=O.[NH4+]>[Pd].O1CCCC1.C(O)C>[CH3:1][N:2]([C:5]([C:7]1[CH:8]=[CH:9][C:10]([CH:13]([CH3:30])[C:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])([OH:21])[CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)=[CH:11][CH:12]=1)=[O:6])[O:3][CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86755080HCID 86755080, compound

Product 1

HCID 54117983HCID 54117983, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of N,O-dimethyl-4-(2-[2,4-difluorophenyl]-2-hydroxy-1-[1,2,4-triazol-1-yl]-3-buten-3-yl) benzene hydroxamic acid (0.9 g, 2.2 mmol-see Preparation 50), 10% palladium on charcoal (0.2 g) and ammonium formate (0.68 g, 11 mmol) was suspended in a tetrahydrofuran/ethanol (1:1, 40 ml) solution and heated under reflux for 3 hours. The cooled suspension was filtered through "Arbocel" and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (50 ml) and the solution was washed with saturated sodium carbonate solution (20 ml) and brine (20 ml), then dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica by gradient elution with dichloromethane followed by dichloromethane/methanol (39:1). Fractions containing the desired product were combined and evaporated under reduced pressure to yield the title compound (0.5 g, 55%) as a colourless foam.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe cooled suspension was filtered through "Arbocel"
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  6. washthe solution was washed with saturated sodium carbonate solution (20 ml) and brine (20 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica by gradient elution with dichloromethane
  10. additionFractions containing the desired product
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0d61a37a9b454357b16f16180b182fd4
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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