Sodium Carbonate → HCID 66697798, compound

HRID 340591Notes

Reaction equation

HRID 340591 reaction equation
[F:1][C:2]1[C:7]([N:8]2[C:12](OS(C(F)(F)F)(=O)=O)=[CH:11][C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([SH:33])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33][C:12]2[N:8]([C:7]3[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=3)[N:9]=[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:11]=2)=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 677894-FluorothiophenolHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86664252HCID 86664252, compound

Product 1

HCID 66697798HCID 66697798, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A solution of ethyl 1-(2-fluoropyridin-3-yl)-5-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrazole-3-carboxylate (353 mg), 4-fluorobenzenethiol (130 mg) and sodium carbonate (146 mg) in toluene (5 mL) was sufficiently deaerated. Tris(dibenzylideneacetone)dipalladium(0) (8.4 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (11 mg) were added and the mixture was further deaerated. The mixture was stirred under an argon atmosphere at 110° C. for 3 hr, allowed to cool to room temperature, ethyl acetate was added, and the mixture was filtered through a silica gel pad. The organic layer of the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was silica gel column chromatography (eluent:hexane-ethyl acetate=19:1→2:1) to give the title compound as a crude yellow oil (yield 203 mg).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe mixture was filtered through a silica gel pad
  3. washThe organic layer of the filtrate was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12aec013252d4aee928f2200a88bfc55
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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