Sodium Bicarbonate → 1-[3-Fluoro-4-(methylsulfonyl)phenyl]-5-[4-(3-furyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole

HRID 497216Notes

Reaction equation

HRID 497216 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[C:15]([F:23])[CH:14]=3)[N:11]=[C:10]([C:24]([F:27])([F:26])[F:25])[CH:9]=2)=[CH:4][CH:3]=1.[O:28]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29]1.C([O-])(O)=O.[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:23][C:15]1[CH:14]=[C:13]([N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:30]4[CH:31]=[CH:32][O:28][CH:29]=4)=[CH:3][CH:4]=3)=[CH:9][C:10]([C:24]([F:27])([F:26])[F:25])=[N:11]2)[CH:18]=[CH:17][C:16]=1[S:19]([CH3:22])(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734358Furan-3-boronic acidHCID 223167185-(4-bromophenyl)-1-[3-fluoro-4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 223168561-[3-Fluoro-4-(methylsulfonyl)phenyl]-5-[4-(3-furyl)phenyl]-3-(trifluoromethyl)-1H-pyrazoleYield 45.2%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 5-(4-bromophenyl)-1-[3-fluoro-4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole (0.15 g, 0.324 mmol) in DME (3.9 mL) was added furan-3-boronic acid (0.044 g, 0.389 mmol), bis(triphenylphosphine)palladium(II)chloride (0.025 g, 0.04 mmol) and saturated NaHCO3 solution (1.3 mL) at room temperature under nitrogen. The mixture was heated at reflux temperature for 4 hours, and cooled down to room temperature. The reaction mixture was filtered through celite, the filtrate was poured into water and the whole was extracted with ethyl acetate (20 mL×3). The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane/ethyl acetate (3/1) to give the title compound (0.066 g, 45.2% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 4 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. additionthe filtrate was poured into water
  5. extractionthe whole was extracted with ethyl acetate (20 mL×3)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. washeluting with hexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-e4f1b91e9d924b66b4ed15c207837120
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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