6-Nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole → HCID 67293196, compound
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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)+.