4-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole → 3-ethyl-1-((4-methylthiazol-2-yl)methyl)-1H-indazol-4-amine

HRID 79472Notes

Reaction equation

HRID 79472 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=3)[C:10]([CH:20]=[CH2:21])=[N:9]2)[S:5][CH:6]=1>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:20]([C:10]1[C:11]2[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][C:16]=2[N:8]([CH2:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[N:9]=1)[CH3:21]

Participants

4

Reactant 1

HCID 672609244-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole

Product 1

HCID 672602643-ethyl-1-((4-methylthiazol-2-yl)methyl)-1H-indazol-4-amineYield 83%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole (0.249 g, 0.829 mmol) in hot ethanol (8 mL) was purged with argon and treated with Pearlman's catalyst (124 mg). The mixture was purged with argon, purged with hydrogen gas and allowed to stir at ambient temperature under hydrogen gas for 14 hours. The mixture was filtered through glass fiber filter paper, washed with methanol and concentrated to afford 3-ethyl-1-((4-methylthiazol-2-yl)methyl)-1H-indazol-4-amine (187 mg, 83%) as a pale yellow oil.

Workup

  1. customThe mixture was purged with argon
  2. custompurged with hydrogen gas
  3. filtrationThe mixture was filtered through glass fiber
  4. filtrationfilter paper
  5. washwashed with methanol
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7ec5468c794b4271aea75993a4058f80
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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