Piperidine → 5-(3-bromo-pyridin-5-yl)-1-(2,4-difluoro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

HRID 2207896Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10](=O)[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:5]=[N:6][CH:7]=1.Cl.[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[NH:28][NH2:29].N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:8]2[N:28]([C:22]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=3[F:20])[N:29]=[C:10]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH2:9]2)[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1-(5-Bromo-pyridin-3-yl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one (2.9 g, 8.6 mmol) prepared in Step 3, 2,4-difluorophenylhydrazine hydrochloride (2.4 g, 8.6 mmol), and piperidine (1.7 mL, 17.3 mmol) were added to ethanol (86.4 mL). The reaction mixture was stirred at 90° C. for 18 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The mixture was washed with distilled water, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9) to give 2.4 g of the titled compound as a yellow solid.

Workup

concentrationconcentrated under reduced pressure
additionethyl acetate was added
washThe mixture was washed with distilled water
dry with materialdried on anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto give a yellow liquid residue
customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record: ord-22398f6c30bb4cb8a5d1dd3bf73f2c5e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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