5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole → 1-(Pyridin-2-ylmethyl)-1H-indazol-5-amine

HRID 1815917Notes

Reaction equation

HRID 1815917 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[N:8]=[CH:7]2)([O-])=O>CO.CCOC(C)=O.[Pd]>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:9]1[C:10]2[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

5

Reactant 1

HCID 224961495-nitro-1-(pyridin-2-ylmethyl)-1H-indazole

Product 1

HCID 219523661-(Pyridin-2-ylmethyl)-1H-indazol-5-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 5-nitro-1-pyridin-2-ylmethyl-1H-indazole (Step 1) (671 mg, 2.63 mmol) in MeOH (15 mL) and EtOAc (5 mL) at RT was added a slurry of 10% Pd/C (150 mg) in MeOH (5 mL). The resulting slurry was stirred under a balloon of H2 for 1.75 h, filtered through Celite®, and rinsed with MeOH and EtOAc. Concentration of the filtrate gave 1-pyridin-2-ylmethyl-1H-indazol-5-ylamine.

Workup

  1. filtrationfiltered through Celite®
  2. washrinsed with MeOH and EtOAc

Sources & evidence

ORD record
ord-617e7fed4e704d17b7cc25f2c7a5e896
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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