Ethyl Acetate → HCID 22472993, compound

HRID 2183726Notes

Reaction equation

HRID 2183726 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][N:19]=4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C(OCC)(=O)C>CO.[Pt](=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C:18]4[N:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 22472972HCID 22472972, compound

Product 1

HCID 22472993HCID 22472993, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(4-Fluoro-phenyl)-5-(5-nitro-pyridin-2-yloxy)-1H-indazole (0.28 g, 0.79 mmol) in 10 mL of methanol was added 10 mL of ethyl acetate and 30 mg of platinum (IV) oxide. After shaking under 50 psi of H2 for 3 h, the mixture was filtered through a pad of Celite and concentrated in vacuo, affording 0.25 g of 6-[1-(4-Fluoro-phenyl)-1H-indazol-5-yloxy]-pyridin-3-ylamine as a colorless solid. 1H NMR (CD3OD, 400 MHz): δ 8.96 (d, 1H, J=2.8 Hz), 8.58 (dd, 1H, J=2.8, 9.2 Hz), 8.25 (s, 1H), 7.6-7.8 (m, 3H), 7.66 (1H, d, 2.4 Hz), 7.3-7.2 (m, 3H), 7.19 (d, 1H, J=9.2 Hz) ppm.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0e2bc112add415ca6a0e728f3ebf939
Source dataset
uspto-grants-2005_05
Patent number
US06900201B2

Reaction notes

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