Methyl 1-(1-methylethyl)-6-nitro-1H-indazole-4-carboxylate → Methyl 6-amino-1-(1-methylethyl)-1H-indazole-4-carboxylate

HRID 1476477Notes

Reaction equation

HRID 1476477 reaction equation
[CH3:1][CH:2]([N:4]1[C:12]2[CH:11]=[C:10]([N+:13]([O-])=O)[CH:9]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[C:7]=2[CH:6]=[N:5]1)[CH3:3]>C(O)C.[Pd]>[NH2:13][C:10]1[CH:9]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[C:7]2[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:12]=2[CH:11]=1

Participants

4

Reactant 1

HCID 67468642Methyl 1-(1-methylethyl)-6-nitro-1H-indazole-4-carboxylate

Product 1

HCID 67468220Methyl 6-amino-1-(1-methylethyl)-1H-indazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 1-(1-methylethyl)-6-nitro-1H-indazole-4-carboxylate (1.39 g, 5.28 mmol) was dissolved in ethanol (70 mL) and hydrogenated using an H-Cube instrument (full H2 mode and 10% Pd/C). The solvent was removed in vacuo and the residue was purified via silica gel chromatography (eluent: 0% to 40% gradient; EtOAc:Hex). The product was obtained as 1.05 g (85%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.58 (d, J=6.57 Hz, 6H), 4.00 (s, 5H), 4.70 (dt, J=13.39, 6.69 Hz, 1H), 6.80 (s, 1H), 7.37 (d, J=2.02 Hz, 1H), 8.30 (s, 1H). LCMS (ES) [M+H]+ 234.0

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified via silica gel chromatography (eluent: 0% to 40% gradient; EtOAc:Hex)
  3. customThe product was obtained as 1.05 g (85%)

Sources & evidence

ORD record
ord-117b0d3cad084d7fbaa5520cf0917e0a
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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