4-Fluoro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole → 3-(4-fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine

HRID 407429Notes

Reaction equation

HRID 407429 reaction equation
[F:1][C:2]1[CH:3]=[N:4][N:5]([CH3:18])[C:6]=1[C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:8]=1[O:16][CH3:17]>CCO.[Pd]>[F:1][C:2]1[CH:3]=[N:4][N:5]([CH3:18])[C:6]=1[C:7]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:8]=1[O:16][CH3:17]

Participants

4

Reactant 1

HCID 231394304-Fluoro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole

Product 1

HCID 231394493-(4-fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Fluoro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (109 mg, 0.434 mmol) in EtOH (10 mL) was treated with Pd—C (10 wt. %, Degussa) and a balloon of H2 was allowed to bubble through the slurry. The reaction mixture was filtered through celite and the solvent was removed under reduced pressure to afford 93 mg (97%) of 3-(4-fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine as a light brown oil. LCMS m/z (%)=222 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ: 7.38 (d, JH,F=4.4 Hz, 1H), 6.86 (d, J=8.8 Hz, 1H), 6.78 (dd, J1=8.8 Hz, J2=2.8 Hz, 1H), 6.63 (d, J=2.8 Hz, 1H), 3.74 (s, 3H), 3.68 (s, 3H), 3.53 (s, 2H). 19F NMR (376 MHz, CDCl3) δ: −175.50 (d, JH,F=5.3 Hz, 1F).

Workup

  1. customto bubble through the slurry
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2ce0cd0790d241ea82bf22ab0481f3a4
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

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