4-(azidomethyl)-1-(4-iodophenyl)-1H-pyrazole → (1-(4-iodophenyl)-1H-pyrazol-4-yl)methanamine

HRID 643029Notes

Reaction equation

HRID 643029 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[N:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)[CH:9]=1)=[N+]=[N-]>CO.[Ni]>[I:16][C:13]1[CH:12]=[CH:11][C:10]([N:8]2[CH:9]=[C:5]([CH2:4][NH2:1])[CH:6]=[N:7]2)=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 866140084-(azidomethyl)-1-(4-iodophenyl)-1H-pyrazole

Product 1

HCID 68507921(1-(4-iodophenyl)-1H-pyrazol-4-yl)methanamineYield 81.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(azidomethyl)-1-(4-iodophenyl)-1H-pyrazole (530 mg, 1.63 mmol) and Ra—Ni (50% aq. slurry, 200 mg) in MeOH (3 mL) was hydrogenated under balloon H2 for 1 hr. It was filtered through celite. The filtrate was concentrated in vacuo to give (1-(4-iodophenyl)-1H-pyrazol-4-yl)methanamine (396 mg).

Workup

  1. filtrationIt was filtered through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9d927dbb347f4c57b57d9a8092397621
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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