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

HRID 842362Notes

Reaction equation

HRID 842362 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-073e2575282b4c26ae7a4a47064dc8c0
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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