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

HRID 539773Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:21])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N+:18]([O-])=O)[CH:12]=3)[N:10]=2)[N:7]=1.CC(O)=O>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:21])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([CH:12]=3)[NH2:18])[N:10]=2)[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 6-chloro-3-methyl-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (2.00 g, 6.60 mmol) in ethanol (100 mL) and water (25 mL) containing AcOH (39.6 mmol) is added iron (1.84 g, 33.0 mmol). The mixture is heated at 80° C. for 6 hours, then 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 is purified via chromatography (hexanes to EtOAc) to afford the title compound (1.45 g, 80%) as a yellow solid: Rf 0.52 (EtOAc); LCMS (m/z)=273.3, 275.3 [M+H]+, tR=1.79 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 is purified via chromatography (hexanes to EtOAc)

Sources & evidence

ORD record: ord-1e49ecb1d0a947009bd66d0dc089a372
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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