1,1-Dimethylethyl 3-(3-fluorophenyl)-5-nitro-1H-indazole-1-carboxylate → 1h-Indazole-1-carboxylic acid,5-amino-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

HRID 1610083Notes

Reaction equation

HRID 1610083 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=3)[N:10]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[H][H]>O1CCCC1.[Pd]>[NH2:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])[N:9]=[C:8]2[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 2

HCID 222608791,1-Dimethylethyl 3-(3-fluorophenyl)-5-nitro-1H-indazole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 222606241h-Indazole-1-carboxylic acid,5-amino-3-(3-fluorophenyl)-,1,1-dimethylethyl esterYield 111.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 180 mg of tert-butyl 3-(3-fluorophenyl)-5-nitro-1H-1-indazolecarboxylate in 10 ml tetrahydrofuran was added 100 mg of palladium (5%)-carbon, and the mixture was stirred at room temperature in an atmosphere of hydrogen gas at normal pressure for 3 hours. The reaction mixture was filtrated through Celite and the solvent was evaporated, to give 184 mg of the title compound as a light brown oil.

Workup

  1. filtrationThe reaction mixture was filtrated through Celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b62ad98817324eca91abb121a39e7003
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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