Ethanol → Ethyl 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate

HRID 930997Notes

Reaction equation

HRID 930997 reaction equation
[Br:1][C:2]1[C:3]([NH2:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][O-].[K+].S(=O)(=O)(O)O.C(O)C>C(OCC)(=O)C>[Br:1][C:2]1[C:3]2[N:4]([C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:12]=2)[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 130641553-Bromo-5-(trifluoromethyl)pyridin-2-amineHCID 74089075Potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 118378965Ethyl 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromo-5-(trifluoromethyl)pyridin-2-amine (3.0 g), potassium 2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate (5.4 g), sulfuric acid (0.80 mL) and ethanol (60 mL) was stirred overnight at 90° C. The reaction mixture was diluted with ethyl acetate, and washed with water. The aqueous layer was neutralized with 1N sodium hydroxide, and extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was suspended in a mixed solvent of IPE and hexane, and the obtained solid was collected by filtration to give the title compound (2.6 g).

Workup

  1. washwashed with water
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. filtrationthe obtained solid was collected by filtration

Sources & evidence

ORD record
ord-b4711972c09c4f17bf5cf9832d26bb7e
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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