Ammonium formate → 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine

HRID 1269874Notes

Reaction equation

HRID 1269874 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 694285754-methyl-5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazole

Product 1

HCID 694312064-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amineYield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-methyl-5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazole (1.06 g, 4.06 mmol) in ethanol (20 ml) were added 10% Pd—C (200 mg) and ammonium formate (1.28 g, 20.3 mmol), and the resulting mixture was heated under reflux for 1 hour. After the solid was removed by filtration using Celite, water, ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added to the residue. The resulting mixture was extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (955 mg, 100%) was obtained.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customAfter the solid was removed by filtration
  4. additiona saturated aqueous sodium hydrogencarbonate solution were added to the residue
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-3950c0a607e04f6fa78764169b4eb585
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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