6-Chloro-2-(4-methyl-3-nitro-phenyl)imidazo[2,1-f]pyridazine → 5-(6-Chloroimidazo[2,1-f]pyridazin-2-yl)-2-methyl-aniline

HRID 539788Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Iron (1.34 g) is added to a mixture of 6-chloro-2-(4-methyl-3-nitro-phenyl)imidazo[2,1-f]pyridazine (1.15 g, 0.004 mol) and EtOH—AcOH (120 mL, 2:1). The mixture is stirred at 80° C. for 2 hours, cooled to room temperature, filtered through celite which is washed with EtOAc, and concentrated. The oily residue is dissolved in EtOAc (500 mL) and washed once with sat. NaHCO3 (200 mL). Organic layer is dried and concentrated to give the title compound (0.85 g, 82%), which is used without further purification. LCMS m/z=259.4 [M+H]+, tR=1.64 min.

Workup

temperaturecooled to room temperature
filtrationfiltered through celite which
washis washed with EtOAc
concentrationconcentrated
dissolutionThe oily residue is dissolved in EtOAc (500 mL)
washwashed once with sat. NaHCO3 (200 mL)
customOrganic layer is dried
concentrationconcentrated

Sources & evidence

ORD record: ord-7dc52769f8364ff281676b74645f9476
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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