(4-Fluorophenyl)hydrazine → 3-(4-chlorophenoxy)-5-fluoro-2-methyl-1H-indole

HRID 2233735

Reaktionsgleichung

Reaktionsgleichung von HRID 2233735
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20]N)=[CH:16][CH:15]=1>C(O)C>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][C:7]2[C:18]3[C:17](=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=3)[NH:20][C:8]=2[CH3:9])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 69982(4-Fluorophenyl)hydrazineHCID 2398741-(4-Chlorophenoxy)acetone

Produkt 1

HCID 117018033-(4-chlorophenoxy)-5-fluoro-2-methyl-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1-(4-Chloro-phenoxy)-propan-2-one (2.05 g) was added to a stirred solution of (4-fluoro-phenyl)-hydrazine (1.4 g) in ethanol (30 ml) at RT. After 2 h, the solvent was removed under reduced pressure and the residue dissolved in DCM (30 ml). Phosphorus trichloride (1.06 ml) was added dropwise to the solution and after stirring at RT for 16 h the reaction was quenched with aq. sodium hydrogencarbonate solution. The mixture was extracted with DCM, the organics washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane. Yield 0.75 g

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in DCM (30 ml)
  3. additionPhosphorus trichloride (1.06 ml) was added dropwise to the solution
  4. customwas quenched with aq. sodium hydrogencarbonate solution
  5. extractionThe mixture was extracted with DCM
  6. washthe organics washed with water
  7. customdried
  8. customevaporated under reduced pressure
  9. customThe residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-58e7debb475743fc80e44a9d88bdd9ce
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709521B2

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