Potassium Carbonate → 6-Bromo-2-(trifluoromethyl)imidazo(1,2-a)pyridine

HRID 2366359Notes

Reaction equation

HRID 2366359 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.Br[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:8]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 706222-Amino-5-bromopyridineHCID 790083-Bromo-1,1,1-trifluoro-2-propanone

Product 1

HCID 199734446-Bromo-2-(trifluoromethyl)imidazo(1,2-a)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromopyridin-2-amine (2 g, 11.56 mmol), 3-bromo-1,1,1-trifluoropropan-2-one (1.44 mL, 2.65 g, 13.87 mmol) and potassium carbonate (2.4 g, 17.34 mmol) and 15 mL of ethanol was heated in a microwave vial to 120° C. for 30 min. The mixture was concentrated, and the residue was partitioned between DCM and water. The organic phase was concentrated and purified by flash chromatography on silica gel using MBTE/heptane as the eluent. Product was isolated as an off-white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between DCM and water
  3. concentrationThe organic phase was concentrated
  4. custompurified by flash chromatography on silica gel using MBTE/heptane as the eluent
  5. customProduct was isolated as an off-white solid

Sources & evidence

ORD record
ord-ae7e7b520d3f426ea2805479e72330a2
Source dataset
uspto-grants-2014_04
Patent number
US08697739B2

Reaction notes

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