3-Bromo-1,1,1-trifluoro-2-propanone → 8-(2,6-Dichlorobenzyloxy)-2-trifluoromethylimidazo[1,2-a]pyridine

HRID 1290160Notes

Reaction equation

HRID 1290160 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:19][C:20](=O)[C:21]([F:24])([F:23])[F:22]>C(O)C>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=1[CH2:9][O:8][C:7]1[C:2]2[N:3]([CH:19]=[C:20]([C:21]([F:24])([F:23])[F:22])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 103783682-Amino-3-(2,6-dichlorobenzyloxy)pyridine

Product 1

HCID 105947188-(2,6-Dichlorobenzyloxy)-2-trifluoromethylimidazo[1,2-a]pyridineYield 44.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-(2,6-dichlorobenzyloxy)-pyridine (1.345 g) and 3-bromo-1,1,1-trifluoroacetone (1.147 g) in ethanol (26 ml) was refluxed for 5 hours, cooled, and concentrated in vacuo. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was washed with water, dried, and concentrated under reduced pressure to give a solid, which was purified by flash chromatography on silica gel to give 8-(2,6-dichlorobenzyloxy)-2-trifluoromethylimidazo[1,2-a]pyridine as a white solid (803 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give a solid, which
  9. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f989447a2e8e4fa4852e500c52436d28
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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