4,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedione → 3,5-dichloro-2-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine

HRID 453071

Reaction equation

HRID 453071 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3](=O)[CH2:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.[Cl:15][C:16]1[C:17]([NH:23][NH2:24])=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=1>C(O)(=O)C>[Cl:15][C:16]1[C:17]([N:23]2[C:5]([C:7]3[O:8][CH:9]=[CH:10][CH:11]=3)=[CH:4][C:3]([C:2]([F:14])([F:13])[F:1])=[N:24]2)=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=1

Participants

4

Reactant 2

HCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 6009663,5-Dichloro-2-hydrazinylpyridine

Product 1

HCID 669396863,5-dichloro-2-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridineYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 250 mL flask, 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione (5.50 g, 26.7 mmol), 3,5-dichloro-2-hydrazinylpyridine (4.75 g, 26.7 mmol) and glacial acetic acid (100 mL) were added. The reaction mixture was heated to reflux. When the reaction completed, the reaction mixture was concentrated by rotary evaporator. Then ethyl acetate (300 mL) and water (150 mL) was added, the organic extracts were washed with saturated sodium bicarbonate solution (150 mL) and brine (150 mL) in sequence, dried over anhydrous magnesium sulfate and concentrated by rotary evaporator. The residue was purified by silica gel column chromatography (Fluent: ethyl acetate/petroleum ether=1/5) to give the product (5.66 g) as a yellow oil in 61% yield. 1H NMR (300 MHz, CDCl3): 8.514 (d, 1H), 7.974 (d, 1H), 7.362 (d, 1H), 6.917 (s, 1H), 6.388 (dd, 1H), 6.148 (d, 1H).

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. concentrationthe reaction mixture was concentrated by rotary evaporator
  3. additionThen ethyl acetate (300 mL) and water (150 mL) was added
  4. washthe organic extracts were washed with saturated sodium bicarbonate solution (150 mL) and brine (150 mL) in sequence
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by rotary evaporator
  7. customThe residue was purified by silica gel column chromatography (Fluent: ethyl acetate/petroleum ether=1/5)

Sources & evidence

ORD record
ord-d8074549ef634c59aad5111feb4bc17c
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Linked notes

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