HCID 67293404, compound → 3-Methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-amine

HRID 1038850Notes

Reaction equation

HRID 1038850 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:3]=1>CO.[Pd]>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[N:4]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:21])[CH3:20])[N:3]=1

Participants

4

Reactant 1

HCID 67293404HCID 67293404, compound

Product 1

HCID 592766553-Methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazol-6-amineYield 88.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-methyl-6-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (2.37 g, 7.70 mmol) and Pd/C (10 weight %) (0.082 g, 0.77 mmol) in MeOH (35 mL) was stirred under an atmosphere of H2 at about 25° C. for about 12 h. The hydrogen source was removed and the flask was purged with N2. The catalyst was removed by filtration and the filtrate was concentrated to give 3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-amine (1.9 g, 84%): LC/MS (Table 2, Method h) Rt=2.09 min; MS m/z: 278 (M+H)+.

Workup

  1. customThe hydrogen source was removed
  2. customthe flask was purged with N2
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-364e673b3daa4a96bfbf1a4d04bfe0c2
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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