1-(2-fluoro-4-nitrophenyl)-1H-pyrazole → [3-fluoro-4-(1H-pyrazol-1-yl)phenyl]amine

HRID 56132Notes

Reaction equation

HRID 56132 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1>C(Cl)Cl.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1)[NH2:8]

Participants

4

Reactant 1

HCID 107035141-(2-fluoro-4-nitrophenyl)-1H-pyrazole

Product 1

HCID 10725981[3-fluoro-4-(1H-pyrazol-1-yl)phenyl]amineYield 46%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-fluoro-4-nitrophenyl)-1H-pyrazole (3.31 g, 16 mmol) in CH2Cl2 (60 mL) was added catalyst Pd/C (0.33 g). The reaction mixture was stirred at rt under H2 overnight, and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=1:1) to give the title compound as a white solid (1.30 g, 46%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/CH2Cl2 (V/V)=1:1)

Sources & evidence

ORD record
ord-d4ebabb531a34ecbbe313de7498869ac
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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