1-(3-fluorobenzyl)-5-nitro-1H-indazole → 1-(3-Fluorobenzyl)-1H-indazol-5-amine

HRID 415022

Reaction equation

HRID 415022 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-])=O)=[CH:12][CH:13]=2)[CH:8]=[N:7]1>CCO.[Pt]>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH2:15])=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

4

Reactant 1

HCID 219664901-(3-fluorobenzyl)-5-nitro-1H-indazole

Product 1

HCID 71470731-(3-Fluorobenzyl)-1H-indazol-5-amine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Follow modified procedure from WO 99/35146. 1-(3-Fluoro-benzyl)-5-nitro-1H-indazole (2.49 g, 9.2 mmol) is suspended in 40 ml absolute EtOH and Pt/C (5%, wet, 150 mg) is added. The reaction mixture is stirred and heated at 60° C. under a hydrogen atmosphere (balloon). Roughly 4 hours into the reaction LC/MS reveals the formation of substantial amounts of product. The mixture is filtered through Celite and concentrated under reduced pressure. Yield: 2.01 g (90.8%) of a white solid.

Workup

  1. customRoughly 4 hours into the reaction LC/MS
  2. filtrationThe mixture is filtered through Celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff116f94cb45417cb577c54f4cff4800
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Linked notes

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