4-Nitro-2-(tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazole → 2-(Tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine

HRID 1695711Notes

Reaction equation

HRID 1695711 reaction equation
[N+:1]([C:4]1[C:5]2[C:9]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][O:21]4)=[CH:15][CH:14]=3)[CH:12]=1)=[N:8][N:7]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1)[CH:6]=2)([O-])=O>C(OCC)(=O)C.[Pd]>[O:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]1[N:7]1[CH:6]=[C:5]2[C:9]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]4[CH2:25][CH2:24][CH2:23][CH2:22][O:21]4)=[CH:15][CH:14]=3)[CH:12]=[C:4]2[NH2:1])=[N:8]1

Participants

4

Reactant 1

HCID 582557524-Nitro-2-(tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazole

Product 1

HCID 582558372-(Tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazol-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitro-2-(tetrahydro-2H-pyran-2-yl)-6-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]-2H-indazole (2.31 g, 5.45 mmol) was dissolved in ethyl acetate (109 ml) and the compound was reduced using the H-cube (available from ThalesNano) with a 10% Pd/C catalyst cartridge at 30° C. and 30 bar. The solvent was removed in vacuo and the residue was purified using silica gel chromatography eluting with 0-50% ethyl acetate in cyclohexane. Appropriate fractions were combined and the solvent was removed in vacuo to give the title compound, 963 mg.

Workup

  1. customat 30° C.
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified
  4. washeluting with 0-50% ethyl acetate in cyclohexane
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4a1540bcca5c4076be58de5ca17eeae2
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

Loading…