Ethyl Acetate → 3-Fluoro-4-(6-(pyridine-4-yl)-1H-indazole-5-yloxy)aniline

HRID 1661982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1661982
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[NH:10][N:9]=[CH:8]2.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+].CCOC(C)=O>CCOC(C)=O.CCO>[F:1][C:2]1[CH:23]=[C:22]([CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[NH:10][N:9]=[CH:8]2)[NH2:24]

Komponenten

6

Edukt 4

HCID 8857Ethyl Acetate2×HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 667667865-(2-fluoro-4-nitrophenoxy)-6-(pyridine-4-yl)-1H-indazole

Produkt 1

HCID 667668543-Fluoro-4-(6-(pyridine-4-yl)-1H-indazole-5-yloxy)anilineAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584252Ethanol ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-(2-fluoro-4-nitrophenoxy)-6-(pyridine-4-yl)-1H-indazole (1.95 g, 4.5 mmol) and SnCl2.2H2O (10.2 g, 45.3 mmol) in EtOAc/EtOH (200 mL/10 mL) is stirred at 80° C. for 2 hours. Then aqueous NaHCO3 and EtOAc are added. The organic phase is dried over anhydrous MgSO4 and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (2:1) to give the desired product (1.10 g, 61.0% yield). MS (m/z): 321.0 (M+H).

Aufarbeitung

  1. dry with materialThe organic phase is dried over anhydrous MgSO4
  2. concentrationconcentrated
  3. customThe residue is purified by silica gel column chromatography
  4. washeluting with PE

Quellen und Nachweise

ORD-Eintrag
ord-48cc594eb1ef407f87b60aafbd8974bc
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030302B2

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