Acetic Acid → 5-(3-Chloro-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

HRID 539736

Reaction equation

[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([N+:20]([O-])=O)[CH:14]=1.CC(O)=O>C(O)C.O.[Fe]>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH:14]=1)[NH2:20]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 3-chloro-6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (0.25 g, 0.784 mmol) in ethanol (50 mL) and water (10 mL) containing AcOH (4.70 mmol) is added iron (0.218 g, 3.92 mmol). The reaction mixture is heated at 80° C. for 2 hours, cooled, concentrated under reduced pressure and sat. aqueous NaHCO3 (100 mL) is added. The mixture is extracted with EtOAc (3×50 mL). 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 (0.201 g, 89%) as a yellow solid: Rf 0.32 (EtOAc); LCMS (m/z)=289.4, 291.2 [M+H]+, tR=2.21 min.

Workup

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

Sources & evidence

ORD record: ord-ea0b4462ee78402a8a736f7b50068a21
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Linked notes

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