Selectfluor → 3-(4-Fluoro-1-phenyl-1h-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1h)-one

HRID 2089957Notes

Reaction equation

HRID 2089957 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[B-](F)(F)(F)[F:30].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N.[Cl-].[Na+].O>[F:30][C:10]1[CH:9]=[N:8][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]=1[C:12]1[C:17](=[O:18])[CH:16]=[CH:15][N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[CH:20]=2)[N:13]=1

Participants

5

Reactant 2

HCID 2724933Selectfluor5×HCID 462198193-(1-Phenyl-1h-Pyrazol-5-Yl)-1-[3-(Trifluoromethyl)phenyl]pyridazin-4(1h)-One

Product 1

HCID 580722333-(4-Fluoro-1-phenyl-1h-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1h)-oneYield 23%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3-(1-phenyl-1H-pyrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (49.0 mg, 0.128 mmol) and selectfluor (45.4 mg, 0.128 mmol) in MeCN (1 mL) was stirred at room temperature for 6 days. To the mixture was added selectfluor (45.4 mg, 0.128 mmol) at room temperature. The mixture was stirred at room temperature for 1 day. To the mixture was added selectfluor (45.4 mg, 0.128 mmol) at room temperature. The mixture was stirred at room temperature for 1 day. To the mixture was added selectfluor (45.4 mg, 0.128 mmol) at room temperature. The mixture was stirred at room temperature for 1 day. To the mixture was added selectfluor (272 mg, 0.768 mmol) at room temperature. The mixture was stirred at room temperature for 3 days. The mixture was diluted with brine, extracted with AcOEt, dried over MgSO4, filtered, concentrated in vacuo, purified by column chromatography on silica gel (hexane/AcOEt=50/50 to 0/100) and crystallized with AcOEt/hexane to yield the title compound (11.7 mg, 23% yield) as a pale yellow solid: mp 156-158° C. 1H NMR (DMSO-d6, 300 MHz): δ ppm 6.67 (1H, d, J=8.2 Hz), 7.33-7.50 (5H, m), 7.63-7.83 (4H, m), 7.97 (1H, d, J=4.1 Hz), 8.96 (1H, d, J=8.0 Hz).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 day
  2. stirringThe mixture was stirred at room temperature for 1 day
  3. stirringThe mixture was stirred at room temperature for 1 day
  4. stirringThe mixture was stirred at room temperature for 3 days
  5. extractionextracted with AcOEt
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified by column chromatography on silica gel (hexane/AcOEt=50/50 to 0/100)
  10. customcrystallized with AcOEt/hexane

Sources & evidence

ORD record
ord-9feaffef88874469aa5678b37015cd72
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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