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

HRID 539756Notes

Reaction equation

HRID 539756 reaction equation
[Cl:1][C:2]1[CH: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[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:18])[F:20])=[C:13]([NH2:21])[CH:12]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 679829716-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine

Product 1

HCID 575162705-(6-Chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)anilineYield 96.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron (0.140 g) is added to a mixture of 6-chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine (0.171 g), HOAc (0.230 mL) and EtOH—H2O (2 mL, 4:1). The mixture is stirred at 80° C. for 2 hours, then cooled, concentrated, taken into sat. NaHCO3 aqueous solution, extracted with EtOAc and CH2Cl2. Organics are dried and concentrated to give the title compound (150 mg, 96% yield), which is used without further purification. LCMS m/z=312.4 [M+H]+, tR=1.96 min.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. extractionextracted with EtOAc and CH2Cl2
  4. customOrganics are dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a49cbce4b43c4cb5b1ef272676a7f334
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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