Hydrochloric Acid → 2-(1-phenyl-1H-pyrazol-5-yl)-6-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-one

HRID 1747796Notes

Reaction equation

HRID 1747796 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1.I[C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].Cl>N1C=CC=CC=1.[Cu]>[C:24]1([N:23]2[C:19]([N:13]3[C:12](=[O:15])[CH:11]=[CH:10][C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=4)=[N:14]3)=[CH:20][CH:21]=[N:22]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 124495416-[3-(Trifluoromethyl)phenyl]pyridazin-3-olHCID 149720775-Iodo-1-phenyl-1H-pyrazole

Product 1

HCID 895860692-(1-phenyl-1H-pyrazol-5-yl)-6-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-oneYield 14.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

A suspension of 6-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-one (240 mg), 5-iodo-1-phenyl-1H-pyrazole (540 mg), copper powder (64 mg) and potassium carbonate (415 mg) in pyridine (5 mL) was heated under reflux for 24 hr. The reaction mixture was poured into 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from hexane/ethyl acetate to give the title compound (56.5 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-a94221c081ea4d50a914e6556f8f3cbf
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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