tert-Butyl 5-Nitro-1H-indazole-1-carboxylate → 1,1-Dimethylethyl 5-amino-1H-indazole-1-carboxylate

HRID 497459Notes

Reaction equation

HRID 497459 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11499917tert-Butyl 5-Nitro-1H-indazole-1-carboxylate

Product 1

HCID 198005561,1-Dimethylethyl 5-amino-1H-indazole-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a Paar flask charged with palladium (10 wt % on carbon, 0.44 g) was added ethyl acetate (30 mL) and 5-nitro-indazole-1-carboxylic acid t-butyl ester (1.61 g, 6.2 mmol). The reaction mixture was hydrogenated at 50 psi for 30 minutes with vigorous shaking. The reaction mixture was filtered through a plug of celite. The plug was washed with 20 mL of methanol and the combined filtrates were concentrated in vacuo to give a white solid (1.4 g, 100%). 1H NMR (300 MHz, CDCl3), δ: 7.99 (s, 1H), 7.97 (d, J=10, 1H), 6.94 (dd, J=10, J′=2, 1H), 6.92 (d, J=2, 1H), 1.71 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washThe plug was washed with 20 mL of methanol
  3. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-45f5c42be6234784acc060d2d08d70aa
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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