Ammonium formate → HCID 11666312, compound

HRID 1817492Notes

Reaction equation

HRID 1817492 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:15]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH:26]3[CH2:30]CC[CH2:27]3)[N:18]=2)[OH:16])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]([C:15]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH:26]([CH3:30])[CH3:27])[N:18]=2)=[O:16])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69058487HCID 69058487, compound

Product 1

HCID 11666312HCID 11666312, compoundYield 37.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of [3-(benzyloxy)phenyl]-(1-cyclopentyl-1H-indazol-3-yl)methanol (0.11 g, 0.19 mmol.), ammonium formate (0.071 g, 1.17 mmol) and 10% palladium on carbon (0.09 g) in 10 mL ethanol was heated at reflux for 18 hours. The reaction was filtered (celite) and the cake washed with excess ethanol. The filtrate was concentrated in vacuo. The crude product was purified by HPLC [column: silica gel 150×12 mm (Biotage) at 10 mL/min with methyl-t-butyl ether/hexane, gradient elution, 1:9 to 1:1 over 15 min) to give the title compound (0.020 g) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. filtrationThe reaction was filtered (celite)
  4. washthe cake washed with excess ethanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe crude product was purified by HPLC [column
  7. washsilica gel 150×12 mm (Biotage) at 10 mL/min with methyl-t-butyl ether/hexane, gradient elution, 1:9 to 1:1 over 15 min)

Sources & evidence

ORD record
ord-dc3af978bc9345b9ba891a3aefbdb10a
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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