4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole → 1-(Oxan-2-yl)-1H-indazol-4-amine

HRID 1621367

Reaction equation

HRID 1621367 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)([O-])=O>CCOC(C)=O.[Pd]>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:4]([NH2:1])[C:5]=2[CH:6]=[N:7]1

Participants

4

Reactant 1

HCID 595482984-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Product 1

HCID 441182321-(Oxan-2-yl)-1H-indazol-4-amineYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.05 g, 4247 μmol) in EtOAc (100 mL) was treated with 10% Pd/C (60 mg) and stirred under an atmosphere of H2. The reaction was monitored by LCMS and found to be complete after 22 h. The reaction was filtered and concentrated (caution: tends to foam/bump). The residue was triturated with Et2O to give 1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-amine (892 mg, 96.7% yield) as an off-white solid. 1H NMR (400 MHz, d6-DMSO) δ 8.11 (s, 1H); 7.03 (t, J=7.82 Hz, 1H); 6.74 (d, J=8.22 Hz, 1H); 6.18 (d, J=7.43 Hz, 1H); 5.78 (s, 2H); 5.59-5.67 (m, 1H); 3.82-3.92 (m, 1H); 3.63-3.74 (m, 1H); 2.30-2.45 (m, 1H); 1.96-2.08 (m, 1H); 1.84-1.94 (m, 1H); 1.65-1.80 (m, 1H); 1.55 (br. s., 2H). m/z (ESI, +ve) Found 218 (M+H)+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated (caution: tends to foam/bump)
  3. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-30c048d178f14b42979588732c567a8d
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Linked notes

Loading…