6-Methoxypyridazin-3-amine → 6-Methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine

HRID 539731

Reaktionsgleichung

Reaktionsgleichung von HRID 539731
[CH3:1][O:2][C:3]1[N:8]=[N:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1)=O>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=3)[N:9]=2)[N:8]=1

Komponenten

4

Edukt 2

HCID 816736-Methoxypyridazin-3-amineHCID 38004222-Bromo-1-(4-methyl-3-nitrophenyl)ethan-1-one

Produkt 1

HCID 680891556-Methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazineAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred solution of 6-methoxypyridazin-3-amine (Apollo Scientific, 0.750 g, 5.99 mmol) and 2-bromo-1-(4-methyl-3-nitrophenyl)ethanone (1.54 g, 5.99 mmol) in acetonitrile (20 mL) is heated at 80° C. for 16 hours. The reaction mixture is concentrated to dryness and purified via chromatography (hexanes to EtOAc) to afford the title compound (1.45 g, 85%) as a light yellow solid: Rf 0.45 (1:1 EtOAc:hexanes); LCMS (m/z)=285.4 [M+H]+, tR=7.47 min. (10 min run)

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated to dryness
  2. custompurified via chromatography (hexanes to EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-0bd679a3722445f3b5d6d8b99bb02dc5
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871767B2

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