Acetic Acid → 5-(6-Methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

HRID 539732

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-])=O)[CH:13]=3)[N:11]=2)[N:8]=1.CC(O)=O>C(O)C.O.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH:13]=3)[NH2:19])[N:11]=2)[N:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a stirred solution of 6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (0.5 g, 1.75 mmol) in ethanol (20 mL) and water (5 mL) containing AcOH (10.5 mmol) is added iron (0.491 g, 8.79 mmol). The mixture is heated at 80° C. for 4 hours, cooled, concentrated under reduced pressure, and sat. aqueous NaHCO3 (100 mL) is added. The mixture is extracted with EtOAc (3×50 mL), the organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude product is purified via chromatography (hexanes to EtOAc) to afford the title compound (0.328 g, 73%) as a light yellow solid: Rf 0.21 (EtOAc); LCMS (m/z)=255.5 [M+H]+, tR=4.89 min. (10 min run).

Aufarbeitung

temperaturecooled
concentrationconcentrated under reduced pressure, and sat. aqueous NaHCO3 (100 mL)
additionis added
extractionThe mixture is extracted with EtOAc (3×50 mL)
customthe organic layer is collected
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness
customThe crude product is purified via chromatography (hexanes to EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-ddd418ae27974b6d932f4c31091df64e
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08871767B2

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