2-(4-Methyl-3-nitro-phenyl)-6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazine → 2-Methyl-5-[6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazin-2-yl]aniline

HRID 539808Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:15]([CH:16]=2)[N:14]=[C:13]([C:17]2[C:18]([C:23]([F:26])([F:25])[F:24])=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11]3)=[CH:4][C:3]=1[N+:27]([O-])=O>CCO.CC(O)=O.[Fe]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:15]([CH:16]=2)[N:14]=[C:13]([C:17]2[C:18]([C:23]([F:25])([F:24])[F:26])=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11]3)=[CH:4][C:3]=1[NH2:27]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2-(4-methyl-3-nitro-phenyl)-6-[2-(trifluoromethyl)-3-pyridyl]imidazo[2,1-f]pyridazine (7.986 g, 0.02 mol) in EtOH—AcOH (48 mL, 1:1) is added slowly to a solution of iron powder (6.702 g, 0.12 mol) in EtOH—AcOH (60 mL, 2:1) at 60° C. The mixture is stirred at 70° C. for 60 min, cooled to room temperature, filtered through celite, washed with EtOAc and concentrated. The oily residue is dissolved in EtOAc (500 mL) and washed twice with saturated aqueous NaHCO3 (200 mL). Organic layer is dried and concentrated to afford the title compound as a solid (7.3 g). LCMS (m/z)=370.5 [M+H]+, tR=1.85 min.

Workup

temperaturecooled to room temperature
filtrationfiltered through celite
washwashed with EtOAc
concentrationconcentrated
dissolutionThe oily residue is dissolved in EtOAc (500 mL)
washwashed twice with saturated aqueous NaHCO3 (200 mL)
customOrganic layer is dried
concentrationconcentrated

Sources & evidence

ORD record: ord-8523e1a7c09a40bfa5e085b92db54f11
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

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