HCID 90423530, compound → 3-(3-methyl-1H-pyrazol-1-yl)-5-(trifluoromethyl)aniline

HRID 1050151Notes

Reaction equation

HRID 1050151 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([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)[N:3]=1>CO.[Pd]>[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]2[CH:8]=[C:9]([CH:10]=[C:11]([C:13]([F:15])([F:14])[F:16])[CH:12]=2)[NH2:17])[N:3]=1

Participants

4

Reactant 1

HCID 90423530HCID 90423530, compound

Product 1

HCID 790184503-(3-methyl-1H-pyrazol-1-yl)-5-(trifluoromethyl)anilineYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-methyl-1-(3-nitro-5-(trifluoromethyl)phenyl)-1H-pyrazole (300 mg, 1.106 mmol) in MeOH (10 mL) was added Pd/C (11.77 mg, 0.111 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=0.35) to afford pure product 3-(3-methyl-1H-pyrazol-1-yl)-5-(trifluoromethyl)aniline (300 mg, 1.045 mmol, 94% yield). 1H NMR (400 MHz, CD3OD): δ 8.05 (d, J=2.4 Hz, 1H), 7.18-7.12 (m, 2H), 6.82 (s, 1H), 6.30 (d, J=2.2 Hz, 1H), 2.32 (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=0.35)

Sources & evidence

ORD record
ord-d10143b940294ada8584677c3651feff
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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