tert-Butyl 6-nitro-1H-indazole-1-carboxylate → 1-BOC-6-AMINO-INDAZOLE

HRID 2301810Notes

Reaction equation

HRID 2301810 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=2)[CH:10]=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[CH:10]=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 11694593tert-Butyl 6-nitro-1H-indazole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 120186071-BOC-6-AMINO-INDAZOLE

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 1-Boc-6-nitroindazole (2.5 g, 9.5 mmol) in ethyl acetate (75 mL) under nitrogen was added 10% Pd/C (500 mg). The mixture was placed under vacuum and the atmosphere was replaced with hydrogen (1 atm). After stirring for 12 h, the hydrogen balloon was removed and diatomaceous earth was added. The mixture was then filtered over a pad of diatomaceous earth and the solvent was removed by rotary evaporation to give 2.17 g (98%) of light pink solid.

Workup

  1. customthe hydrogen balloon was removed
  2. additiondiatomaceous earth was added
  3. filtrationThe mixture was then filtered over a pad of diatomaceous earth
  4. customthe solvent was removed by rotary evaporation
  5. customto give 2.17 g (98%) of light pink solid

Sources & evidence

ORD record
ord-0f846d47370b4ade8357796546e0b694
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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