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

HRID 539759Notes

Reaction equation

HRID 539759 reaction equation
[Br: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>[Br: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 679827116-Bromo-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine

Product 1

HCID 575162715-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)anilineYield 81.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

Fe (0.447 g) is added to a mixture of 6-bromo-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridine (0.618 g), HOAc (0.733 mL), and EtOH—H2O (10 mL, 4:1). The mixture is stirred at 80° C. for 2 hours, then concentrated, taken into sat. aqueous NaHCO3 and extracted with EtOAc and CH2Cl2. Organics are dried and concentrated to give the title compound (463 mg), which is used without further purification. LCMS m/z=356.4 [M+H]+, tR=2.04 min.

Workup

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

Sources & evidence

ORD record
ord-9d36e7de0956449e8384b29e2f64eb86
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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