Water → 1-(4-chlorophenyl)-5-iodo-1H-indazole

HRID 1098917

Reaktionsgleichung

Reaktionsgleichung von HRID 1098917
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.F[C:12]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:13]=1[CH:14]=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1C(=O)CCC1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:12]3[C:13](=[CH:16][C:17]([I:20])=[CH:18][CH:19]=3)[CH:14]=[N:10]2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 162170582-Fluoro-5-iodobenzaldehyde

Produkt 1

HCID 593397541-(4-chlorophenyl)-5-iodo-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

4-chlorophenylhydrazine hydrochloride (5.24 g, 29.27 mmol), 2-fluoro-5-iodobenzaldehyde (7.5 g, 30.00 mmol) and cesium carbonate (22.8 g, 69.98 mmol) was suspended in NMP (120 mL) and stirred at ambient temperature for 45 min. The temperature was raised to +160° C. and the reaction mixture was stirred for 1 h, the now black suspension was allowed to reach r.t. Water was added, the slurry was extracted with EtOAc (500 mL. The organic phase was washed with brine (2×). The brine fractions and waterphase was combined and back extracted once with EtOAc. This second EtOAc phase was washed with brine (2×) before combined with the previous EtOAc phase. The organic phases were dried over Na2SO4, filtered and evaporated. The black residue were dissolved in DCM/Heptane (=1/1) and filtered through a silica column, and the column was then further eluted with DCM/Heptane (=1/1) solvent mixture. The fractions containing product was evaporated, residue was dissolved in EtOAc and Heptane was added, evaporation and diluting with Heptane afforded a slurry, the solid material was collected by filtration and washed with Heptane. Yield 2.82 g (27%)

Aufarbeitung

  1. temperatureThe temperature was raised to +160° C.
  2. stirringthe reaction mixture was stirred for 1 h
  3. customto reach r.t
  4. extractionthe slurry was extracted with EtOAc (500 mL
  5. washThe organic phase was washed with brine (2×)
  6. extractionback extracted once with EtOAc
  7. washThis second EtOAc phase was washed with brine (2×)
  8. dry with materialThe organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. dissolutionThe black residue were dissolved in DCM/Heptane (=1/1)
  12. filtrationfiltered through a silica column
  13. washthe column was then further eluted with DCM/Heptane (=1/1) solvent mixture
  14. additionThe fractions containing product
  15. customwas evaporated
  16. dissolutionresidue was dissolved in EtOAc
  17. additionHeptane was added
  18. customevaporation
  19. additiondiluting with Heptane
  20. customafforded a slurry
  21. filtrationthe solid material was collected by filtration
  22. washwashed with Heptane

Quellen und Nachweise

ORD-Eintrag
ord-f3d84a07c4a64bd19fc7d5235ef2b9a2
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143290B2

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