Sodium Carbonate → HCID 66697843, compound

HRID 340599Notes

Reaction equation

HRID 340599 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.[Br:26][C:27]1[CH:28]=[C:29]([SH:33])[CH:30]=[CH:31][CH:32]=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>[Br:26][C:27]1[CH:28]=[C:29]([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:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 80597m-BromobenzenethiolHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86664252HCID 86664252, compound

Product 1

HCID 66697843HCID 66697843, 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 (767 mg), 3-bromobenzenethiol (567 mg) and sodium carbonate (424 mg) in toluene (10 mL) was sufficiently deaerated, tris(dibenzylideneacetone)dipalladium(0) (92 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (116 mg) were added, and the mixture was further deaerated. Under an argon atmosphere at 110° C., the reaction mixture was stirred for 16 hr, and allowed to cool to room temperature. Ethyl acetate was added and the mixture was filtered through a basic silica gel pad. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1) to give the title compound as a crude yellow oil (yield 869 mg).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe mixture was filtered through a basic silica gel pad
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-712173043ce34e62b1f245c0428d4a46
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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