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Lithium Chloride → 2-Fluoro-4-[5-[4-(1,3-thiazol-4-yl)-3-(trifluoromethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide

HRID 396835
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 396835
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16](Br)=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=3)=[CH:11][C:10]([C:24]([F:27])([F:26])[F:25])=[N:9]2)[CH:5]=[CH:4][C:3]=1[S:28]([NH2:31])(=[O:30])=[O:29].C([Sn](CCCC)(CCCC)[C:37]1[N:38]=[CH:39][S:40][CH:41]=1)CCC.[Cl-].[Li+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:37]4[N:38]=[CH:39][S:40][CH:41]=4)=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=3)=[CH:11][C:10]([C:24]([F:27])([F:26])[F:25])=[N:9]2)[CH:5]=[CH:4][C:3]=1[S:28]([NH2:31])(=[O:30])=[O:29]
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Komponenten

7

Edukt 3

HCID 433294Lithium ChlorideHCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 22316629HCID 22316629, Verbindung

Produkt 1

HCID 223169742-Fluoro-4-[5-[4-(1,3-thiazol-4-yl)-3-(trifluoromethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamideAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8857Ethyl AcetateLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-fluoro-4-[5-[4-bromo-3-(trifluoromethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (308 mg, 0.58 mmol) in dioxane (5 ml) was added 4-(tributylstannyl)thiazole (260 mg, 0.70 mmol), tetrakis(triphenylphosphine)palladium (67 mg, 0.058 mmol), lithium chloride (61 mg, 1.45 mmol), and the mixture was heated at reflux temperature for 16 hours. The reaction mixture was cooled down to room temperature, and diluted with ethyl acetate. The whole was washed with saturated potassium fluoride aqueous solution, and the precipitate was removed by filteration through celite. The resulting solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:2) to give title compound (56 mg, 18% yield).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 16 hours
  3. washThe whole was washed with saturated potassium fluoride aqueous solution
  4. customthe precipitate was removed by filteration through celite
  5. extractionThe resulting solution was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography
  10. washeluting with ethyl acetate-hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-430cc9d32ab5462ea814ad2aabf19fda
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06608095B2

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