2,6-Difluoro-N-{1-[(2-methyl-4-nitrophenyl)methyl]-1H-pyrazol-3-yl}benzamide → N-{1-[(4-amino-2-methylphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide

HRID 1946325Notes

Reaction equation

HRID 1946325 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=2[CH3:22])[N:8]=1)=[O:5]>[Pd].C(O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:9]2[CH:10]=[CH:11][C:7]([NH:6][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:26][CH:25]=[CH:24][C:23]=3[F:27])=[N:8]2)=[C:14]([CH3:22])[CH:15]=1

Participants

4

Reactant 1

HCID 595478502,6-Difluoro-N-{1-[(2-methyl-4-nitrophenyl)methyl]-1H-pyrazol-3-yl}benzamide

Product 1

HCID 59547916N-{1-[(4-amino-2-methylphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 10% palladium on activated carbon (wet, degussa type E101 NE/W) (350 mg, 3.29 mmol, Aldrich) was added a solution of 2,6-difluoro-N-{1-[(2-methyl-4-nitrophenyl)methyl]-1H-pyrazol-3-yl}benzamide (for a preparation see Intermediate 32)(1.6 g, 4.30 mmol) in ethanol (80 ml). The solution was hydrogenated for 1.5 h at ambient temperature. The suspension was filtered through a celite cartridge (10 g) and the catalyst residue washed with methanol (50 ml). The solvent was removed in vacuo to give the title compound as a white foam (1.43 g). LCMS: (System 4) MH+=343, tRET=1.50 min.

Workup

  1. filtrationThe suspension was filtered through a celite cartridge (10 g)
  2. washthe catalyst residue washed with methanol (50 ml)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dbb3d61f3cca42e1ad016e371a60f44c
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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