Cesium carbonate → 5-iodo-1-pyridin-3-yl-1H-indazole

HRID 1098896

Reaktionsgleichung

Reaktionsgleichung von HRID 1098896
C(=O)([O-])[O-].[Cs+].[Cs+].F[C:8]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:9]=1[CH:10]=O.Cl.Cl.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][NH2:26])[CH:20]=1>CN1CCCC1=O>[I:16][C:13]1[CH:12]=[C:9]2[C:8](=[CH:15][CH:14]=1)[N:25]([C:21]1[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=1)[N:26]=[CH:10]2

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 162170582-Fluoro-5-iodobenzaldehydeHCID 171324893-Hydrazinylpyridine dihydrochloride

Produkt 1

HCID 597865715-iodo-1-pyridin-3-yl-1H-indazoleAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Cesiumcarbonate (26.84 g, 82.38 mmol) is added to a suspension of 2-fluoro-5-iodobenzaldehyde (6.87 g, 27.46 mmol) and 3-pyridylhydrazine dihydrochloride (5 g, 27.46 mmol) in 136 mL N-methylpyrrolidon. The reaction mixture is stirred overnight at r.t. After checking that the hydrazone has been formed (1H-NMR) the reaction mixture is heated for 4 h at 160° C. The reaction mixture is allowed to cool down and the dark brown suspension is poured on 1000 mL ice water. After vigorously stirring at r.t. for 45 min, the precipitated product is sucked off via a glass microfibre filter, washed with water and dried at the evaporator at 45° C. 8.28 g (93.9%) of the title compound are obtained.

Aufarbeitung

  1. customhas been formed (1H-NMR) the reaction mixture
  2. temperatureis heated for 4 h at 160° C
  3. temperatureto cool down
  4. stirringAfter vigorously stirring at r.t. for 45 min
  5. filtrationfilter
  6. washwashed with water
  7. customdried at the evaporator at 45° C

Quellen und Nachweise

ORD-Eintrag
ord-19031bd0038e4074adb4246bc0b9ca97
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143290B2

Verknüpfte Notizen

Wird geladen…