Ammonium formate → HCID 11601577, compound

HRID 1817490Notes

Reaction equation

HRID 1817490 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]([CH2:26][CH2:27][CH3:28])[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]([CH2:26][CH2:27][CH3:28])[N:18]=2)=[O:16])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69056997HCID 69056997, compound

Product 1

HCID 11601577HCID 11601577, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of [3-(benzyloxy)phenyl]-(1-propyl-1H-indazol-3-yl)methanol (0.067 g, 0.18 mmol.), ammonium formate (0.09 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 (0.022 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-7fd76c68ce3f4052a22754eb9f1e105e
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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