2-(1-(2-Fluoro-4-nitrophenyl)-3-pyrazolyl)pyridine → 3-fluoro-4-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)aniline

HRID 1844504Notes

Reaction equation

HRID 1844504 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][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:12]1.[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:12]1)[NH2:8]

Participants

5

Reactant 2

HCID 867193702-(1-(2-Fluoro-4-nitrophenyl)-3-pyrazolyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 867193713-fluoro-4-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)anilineYield 83.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The above-described product 18a (7.87 g, 27.7 mmol) was dissolved in ethanol (50 mL), together with Pd/C (0.787 g). The mixture was reacted overnight at room temperature with a flow of hydrogen. After completion of the reaction, the solvent was evaporated. After recrystallization with ethyl acetate/petroleum ether, the product 19a (5.9 g) was obtained as a yellow solid, with a yield of 83.4%.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customAfter recrystallization with ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-c7b24cc3dfb14237b20ed5a0dd5004e0
Source dataset
uspto-grants-2015_02
Patent number
US08946436B2

Reaction notes

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