Ammonium formate → HCID 178435259, compound

HRID 1354576Notes

Reaction equation

HRID 1354576 reaction equation
C([N:8]1[C:12]([C:13]2([CH2:23][CH3:24])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([F:22])[CH:19]=3)[CH2:14]2)=[CH:11][N:10]=[CH:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH2:23]([C:13]1([C:12]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([F:22])[CH:19]=2)[CH2:14]1)[CH3:24]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 21106103HCID 21106103, compound

Product 1

HCID 178435259HCID 178435259, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

53 mg of 1-benzyl-5-(2-ethyl-5-fluoro-indan-2-yl)-imidazole, 20 mg of Pd/C, 51 mg of ammonium formate and 2 ml of ethanol were added under nitrogen atmosphere into a round-bottomed flask equipped with a thermometer and a stirring bar. The reaction mixture was stirred at reflux temperature for 6 hours. The mixture was filtered and the filter (Celite™) was washed with ethanol. The reaction mixture was placed back into a round-bottomed flask and an additional 20 mg of Pd/C and 51 mg of ammonium formate were added under nitrogen atmosphere. The mixture was heated to reflux temperature and refluxed for 2 hours. Then the mixture was cooled to room temperature and filtered. The filter (Celite™) was washed with ethanol and after evaporation to dryness, whereby 4-(2-ethyl-5-fluoro-indan-2-yl)-1H-imidazole was obtained. The analytical sample was purified using TLC-plates. The purity was measured by HPLC: 60%. Normally the crude product was used in the following step.

Workup

  1. customequipped with a thermometer and a stirring bar
  2. temperatureat reflux temperature for 6 hours
  3. filtrationThe mixture was filtered
  4. filtrationthe filter (Celite™)
  5. washwas washed with ethanol
  6. customThe reaction mixture was placed back into a round-bottomed flask
  7. additionan additional 20 mg of Pd/C and 51 mg of ammonium formate were added under nitrogen atmosphere
  8. temperatureThe mixture was heated
  9. temperatureto reflux temperature
  10. temperaturerefluxed for 2 hours
  11. filtrationfiltered
  12. filtrationThe filter (Celite™)
  13. washwas washed with ethanol
  14. customafter evaporation to dryness

Sources & evidence

ORD record
ord-5e72febc713e4216bc3279781cd1cc54
Source dataset
uspto-grants-2007_05
Patent number
US07223871B2

Reaction notes

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