Ammonium formate → 1-(methylsulfonyl)-1H-indazol-5-amine

HRID 1269880Notes

Reaction equation

HRID 1269880 reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[CH:7]=[N:6]1)(=[O:4])=[O:3].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[N:6]1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 229340351-(methylsulfonyl)-5-nitro-1H-indazole

Product 1

HCID 229334151-(methylsulfonyl)-1H-indazol-5-amineYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(methylsulfonyl)-5-nitro-1H-indazole (1.00 g, 4.15 mmol) in ethanol (20 ml) were added 10% Pd-C (100 mg) and then ammonium formate (1.57 g, 24.9 mmol), and the resulting mixture was heated under reflux for 1 hour. The solid was removed by filtration using Celite, and the solvent was distilled off under reduced pressure. Ethyl acetate/water was added to the residue, followed by extraction 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 1-(methylsulfonyl)-1H-indazol-5-amine (425 mg, 49%) was obtained.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe solid was removed by filtration
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionEthyl acetate/water was added to the residue
  5. extractionfollowed by extraction 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-bc1a48ff58414aa1a205681fba6db4fa
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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