Acetic Acid → 5-(6-Chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)aniline

HRID 539747Notes

Reaction equation

HRID 539747 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]([C:17]([F:20])([F:19])[F:18])=[C:13]([N+:21]([O-])=O)[CH:12]=3)=[CH:10][N:4]2[N:3]=1.CC(O)=O>[Fe].CCO.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]([C:17]([F:18])([F:19])[F:20])=[C:13]([CH:12]=3)[NH2:21])=[CH:10][N:4]2[N:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 866678486-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[2,1-f]pyridazine

Product 1

HCID 866678495-(6-Chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)anilineYield 96.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron (0.489 g) is added to a mixture of 6-chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[2,1-f]pyridazine (0.600 g, 1.75 mmol), HOAc (0.802 mL), EtOH-water (10 mL, 4:1). The mixture is heated at 80° C. for 2 hours, then cooled, concentrated, taken into sat. aqueous NaHCO3 (50 mL) and extracted with EtOAc (2×50 mL). Organic is dried and concentrated to give the title compound (530 mg), which is used without further purification. LCMS m/z=313.4 [M+H]+, tR=2.82 min.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. extractionextracted with EtOAc (2×50 mL)
  4. customOrganic is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6121d6be0ad149a791c1db9fba8d7f46
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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