Ethyl Acetate → HCID 69577763, compound

HRID 1520231Notes

Reaction equation

HRID 1520231 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].CC(=O)O[CH2:23][CH3:24]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][CH:24]3[CH2:23][CH2:15][CH2:16][NH:8][CH2:6]3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 11499917tert-Butyl 5-Nitro-1H-indazole-1-carboxylate

Product 1

HCID 69577763HCID 69577763, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-nitro-indazole-1-carboxylic acid tert-butyl ester (300 g, 1.1 mol, 1.0 eq) in THF (3 L), and the mixture was hydrogenated at 40° C. with Pd/C (30 g) as catalyst in the presence of H2 (50 psi). The reaction mixture was stirred at 40° C. for 16 hrs. TLC (PE:EA=4:1) showed the reaction was complete. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated to afford the crude 5-amino-indazole-1-carboxylic acid tert-butyl ester (252 g, 95%) which was used directly for next step without purification.

Workup

  1. filtrationAfter uptake of H2, the catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-9b0bef76d8e94eb98665a62bad224831
Source dataset
uspto-grants-2015_07
Patent number
US09073905B2

Reaction notes

Loading…