6-Nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole → HCID 67293196, compound

HRID 1038860Notes

Reaction equation

HRID 1038860 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[CH3:18][Si:17]([CH3:20])([CH3:19])[CH2:16][CH2:15][O:14][CH2:13][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=2)[CH:8]=[N:9]1

Participants

4

Reactant 1

HCID 534045066-Nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

Product 1

HCID 67293196HCID 67293196, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-Nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (19.2 g, 65.4 mmol) and Pd\C (10 wt %, 1.920 g) were combined in MeOH (60 mL). The mixture was allowed to stir under an atmosphere of H2 at ambient pressure and at rt for about 18 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, 10:1 Hex/EtOAc) to give 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-amine (12.3 g, 71%): LC/MS (Table 2, Method h) Rt=2.09 min; MS m/z: 264 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, 10:1 Hex/EtOAc)

Sources & evidence

ORD record
ord-39511f40b9594ecf8d7874aa75d1a427
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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