1-((5-fluoropyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole → 3-ethyl-1-((5-fluoropyridin-2-yl)methyl)-1H-indazol-4-amine

HRID 79478Notes

Reaction equation

HRID 79478 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([N+:18]([O-])=O)[CH:14]=[CH:15][CH:16]=3)[C:11]([CH:21]=[CH2:22])=[N:10]2)=[N:6][CH:7]=1>CCO.[OH-].[OH-].[Pd+2]>[CH2:21]([C:11]1[C:12]2[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][C:17]=2[N:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=2)[N:10]=1)[CH3:22]

Participants

4

Reactant 1

HCID 672598561-((5-fluoropyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

Product 1

HCID 672601453-ethyl-1-((5-fluoropyridin-2-yl)methyl)-1H-indazol-4-amineYield 90.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-((5-fluoropyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole (0.229 g, 0.768 mmol) in EtOH (4 mL) was purged with argon. To this solution was added palladium hydroxide on carbon (91 mg, 40%/wt). The mixture was purged with more argon and then hydrogen. The mixture was then stirred at ambient temperature under hydrogen for 16 hours. The mixture was filtered through GF/F paper, washed with MeOH and concentrated under reduced pressure to give 3-ethyl-1-((5-fluoropyridin-2-yl)methyl)-1H-indazol-4-amine (188 mg) as an amber oil.

Workup

  1. customThe mixture was purged with more argon
  2. filtrationThe mixture was filtered through GF/F paper
  3. washwashed with MeOH
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14548ac1e778422ea8f7eaecf3bf5d43
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…