4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole → 3-(Trifluoromethyl)-5-(4-methyl-1H-pyrazole-1-yl)aniline

HRID 1050148Notes

Reaction equation

HRID 1050148 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([N+:17]([O-])=O)[CH:8]=2)[CH:6]=1>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:8]=[C:9]([CH:10]=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=2)[NH2:17])[CH:6]=1

Participants

4

Reactant 1

HCID 904234844-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole

Product 1

HCID 790184603-(Trifluoromethyl)-5-(4-methyl-1H-pyrazole-1-yl)anilineYield 56.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole (560 mg, 2.065 mmol) in MeOH (10 mL) was added Pd/C (21.98 mg, 0.206 mmol) in one portion. Then the mixture was stirred under H2 for 12 h. LCMS analysis showed the starting material disappeared. The suspension was filtered through a pad of Celite® and the filter cake was washed with MeOH (2 mL). The combined filtrates were concentrated to dryness to give crude product, which was purified by preparative TLC (PE/EA=5/1, Rf=0.25) to afford pure product 3-(4-methyl-1H-pyrazol-1-yl)-5-(trifluoromethyl)aniline (280 mg, 1.158 mmol, 56.1% yield). 1H NMR (400 MHz, CD3OD): δ 7.96 (s, 1H), 7.52 (s, 1H), 7.15 (s, 2H), 6.82 (s, 1H), 2.15 (s, 3H). ES-LCMS: m/z 242.1 (M+H).

Workup

  1. filtrationThe suspension was filtered through a pad of Celite®
  2. washthe filter cake was washed with MeOH (2 mL)
  3. concentrationThe combined filtrates were concentrated to dryness
  4. customto give crude product, which
  5. customwas purified by preparative TLC (PE/EA=5/1, Rf=0.25)

Sources & evidence

ORD record
ord-da2b92a5250447feb62f4dcabe35985c
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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