Lithium Chloride → 5-(4-Ethyl-5-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide

HRID 394891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394891
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[N:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[C:9]=2[CH2:27][CH3:28])=[CH:4][C:3]=1[F:29].C([Sn](CCCC)(CCCC)[C:35]1[N:36]=[CH:37][S:38][CH:39]=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>[CH2:27]([C:9]1[C:10]([C:23]([F:26])([F:25])[F:24])=[N:11][N:12]([C:13]2[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[N:17][CH:18]=2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([C:35]2[N:36]=[CH:37][S:38][CH:39]=2)=[C:3]([F:29])[CH:4]=1)[CH3:28]

Komponenten

7

Edukt 3

HCID 433294Lithium ChlorideHCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 223137915-(5-(4-Bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide

Produkt 1

HCID 178121315-(4-Ethyl-5-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamideAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 5-(5-(4-bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide (450 mg, 0.912 mmol), 4-tributylstannyl-1,3-thiazol (410 mg, 1.095 mmol), tetrakis(triphenylphosphine)palladium (105 mg, 0.091 mmol), lithium chloride (97 mg, 2.281 mmol) in 1,4-dioxane (11 ml) was stirred at reflux for 17 h. After cooling, the mixture was diluted with ethyl acetate, washed with water. The organic layer was dried (MgSO4) and concentrated. This was purified on silica gel eluting with ethyl acetate/hexane (1:3/1:2) to afford 350 mg (77.1%) of the titled compound as a yellow solid.

Aufarbeitung

  1. temperatureat reflux for 17 h
  2. temperatureAfter cooling
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThis was purified on silica gel eluting with ethyl acetate/hexane (1:3/1:2)

Quellen und Nachweise

ORD-Eintrag
ord-9a99fc05fb2f423f8f2046d0148a6afb
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06603008B1

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