HCID 60154821, compound → 2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

HRID 1621368Notes

Reaction equation

HRID 1621368 reaction equation
[N+:1]([C:4]1[C:5]2[C:9]([CH:10]=[CH:11][CH:12]=1)=[N:8][N:7]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[CH:6]=2)([O-])=O>CCOC(C)=O.[Pd]>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[N:7]1[CH:6]=[C:5]2[C:9]([CH:10]=[CH:11][CH:12]=[C:4]2[NH2:1])=[N:8]1

Participants

4

Reactant 1

HCID 60154821HCID 60154821, compound

Product 1

HCID 601548222-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amineYield 28.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole (2.336 g, 9448 μmol) was dissolved in EtOAc (100 mL) and treated with 10% Pd/C (100 mg). The resulting suspension was stirred under an atmosphere of H2. for 16 h after which time reduction was complete. The reaction mixture was filtered, concentrated and purified by flash chromatography on silica (50% EtOAc/hexane) to give 2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (584 mg, 28.5% yield) as a dry orange foam. 1H NMR (400 MHz, d6-DMSO) δ 8.47 (s, 1H); 6.92 (t, J=7.82 Hz, 1H); 6.72 (d, J=8.61 Hz, 1H); 5.99 (d, J=7.04 Hz, 1H); 5.54-5.69 (m, 3H); 3.98 (d, J=11.74 Hz, 1H); 3.63-3.78 (m, 1H); 2.02-2.13 (m, 2H); 1.87-2.00 (m, 1H); 1.65-1.80 (m, 1H); 1.59 (br. s., 2H). m/z (ESI, +ve) Found 218.1 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-77b41f8381824aaba81792bf9b909b3a
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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