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

HRID 539795Notes

Reaction equation

HRID 539795 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH: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)[N:10]=2)[CH:7]=1.CC(O)=O>[Fe].C(O)C.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:20])[F:19])=[C:13]([CH:12]=3)[NH2:21])[N:10]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 575162776-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine

Product 1

HCID 575162785-(6-Chloroimidazo[1,2-a]pyrazin-2-yl)-2-(trifluoromethyl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron (0.726 g) is added to a mixture of 6-chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine (0.891 g), HOAc (1.19 mL), and EtOH—H2O (10 mL, 4:1). The mixture is stirred at 80° C. for 2 hours, cooled, concentrated and taken up into sat. aqueous NaHCO3 and extracted with EtOAc and CH2Cl2. Organic layer is dried and concentrated to give the title compound (813 mg), which is used without further purification. LCMS m/z=313.4 [M+H]+, tR=2.29 min.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. extractionextracted with EtOAc and CH2Cl2
  4. customOrganic layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4fdee28838ad46b696f951ad01edb476
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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