1h-Indazole,4-(2-fluoro-4-nitrophenoxy)- → 3-Fluoro-4-(1H-indazol-4-yloxy)aniline

HRID 16413Notes

Reaction equation

HRID 16413 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][NH:9]2>C(O)C.O1CCCC1.[Pt](=O)=O>[F:1][C:2]1[CH:17]=[C:16]([CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[N:8][NH:9]2)[NH2:18]

Participants

4

Reactant 1

HCID 179793111h-Indazole,4-(2-fluoro-4-nitrophenoxy)-

Product 1

HCID 179793393-Fluoro-4-(1H-indazol-4-yloxy)aniline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Under argon, 60 mg (0.22 mmol) of 4-(2-fluoro-4-nitrophenoxy)-1H-indazole (from example XXV) are initially charged in 5 ml of ethanol/tetrahydrofuran (1:1), 9.97 mg (0.04 mmol) of platinum(IV) oxide are added and the mixture is hydrogenated under atmospheric pressure for 2 hours. The suspension is filtered off through CELITE (diatomaceous earth), the filtercake is washed with ethanol and the filtrate is concentrated under reduced pressure.

Workup

  1. filtrationThe suspension is filtered off through CELITE (diatomaceous earth)
  2. washthe filtercake is washed with ethanol
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d48c9432d27d412c9e71f902df366c04
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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