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

HRID 877106Notes

Reaction equation

HRID 877106 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>CO.[Pd]>[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-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of compound 16.1 (2.71 g, 10 mmol) and palladium 10% on carbon (1.0 g, wet) in methanol (40 mL) was hydrogenated under a hydrogen balloon for 14 hours. The reaction mixture was then filtered through Celite (20 g), rinsed with dichloromethane/methanol (3/1), and concentrated to give the title compound as a white crystalline solid (2.40 g, 100%). The product is used without further purification. LCMS ESI(+) m/z: 242 (M+1).

Workup

  1. customfor 14 hours
  2. filtrationThe reaction mixture was then filtered through Celite (20 g)
  3. washrinsed with dichloromethane/methanol (3/1)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-365991da971347f7834197d1f9674724
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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