Acetic Acid → 5-(3-(4-Fluorophenyl)-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

HRID 539740Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([N+:26]([O-])=O)[CH:20]=2)=[CH:4][CH:3]=1.CC(O)=O>C(O)C.O.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([CH:20]=2)[NH2:26])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 3-(4-fluorophenyl)-6-methoxy-2-(4-methyl-3-nitrophenyl)imidazo[1,2-b]pyridazine (0.075 g, 0.0198 mmol) in ethanol (6 mL) and water (2 mL) containing AcOH (1.18 mmol) is added iron (0.055 g, 0.991 mmol). The reaction mixture is heated at 80° C. for 2 hours, cooled, concentrated under reduced pressure and sat. aqueous NaHCO3 (50 mL) is added. The mixture is extracted with EtOAc (3×20 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 0.065 g (95%) of the title compound as a yellow solid: Rf 0.36 (95:5 CH2Cl2:MeOH); LCMS (m/z)=349.4 [M+H]+, tR=2.31 min.

Workup

temperaturecooled
concentrationconcentrated under reduced pressure and sat. aqueous NaHCO3 (50 mL)
additionis added
extractionThe mixture is extracted with EtOAc (3×20 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-ab125acee47940fa99a8eeaf2311b3f9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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