3-(4-Fluorophenyl)-5-nitro-1H-indazole → 3-(4-fluorophenyl)-1H-indazol-5-amine

HRID 227700Notes

Reaction equation

HRID 227700 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-])=O)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 534397423-(4-Fluorophenyl)-5-nitro-1H-indazole

Product 1

HCID 224802843-(4-fluorophenyl)-1H-indazol-5-amineYield 81.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product from Step (c) (0.5 g, 1.94 mmol) was dissolved in methanol (50 ml) and treated with 5 wt % Palladium on charcoal (0.15 g). The reaction mixture was pressurized with 50 psi of H2 and stirred for 4 hours. The reaction was filtered and concentrated in vacuo to afford the title compound (0.36 g, 81%); MS (ES+) m/e 229 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8bc3732789974c78ae918fca381d4a34
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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