5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole → 1-(Oxan-2-yl)-1H-indazol-5-amine

HRID 1269770Notes

Reaction equation

HRID 1269770 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[CH:7]2)([O-])=O>C(OCC)(=O)C.C(O)C.[Pd]>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[N:9]1[C:10]2[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

5

Reactant 1

HCID 151476265-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Product 1

HCID 229339271-(Oxan-2-yl)-1H-indazol-5-amineYield 55.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazole (3.69 g, 14.9 mmol) in a mixture of ethyl acetate (50 ml) and ethanol (50 ml) was added 10% Pd—C (300 mg), followed by catalytic reduction at ordinary temperature and atmospheric pressure. After completion or the reaction, the catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The resulting residue was suspended in ethyl acetate, and the solid precipitated was collected by filtration and dried under reduced pressure to obtain 1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (1.79 g, 55%).

Workup

  1. customAfter completion or the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe solid precipitated
  5. filtrationwas collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-b9629c3b1b804869acdddbc9a48678fc
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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