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

HRID 1899977Notes

Reaction equation

HRID 1899977 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-9afd8be1d89f477483537455e19948d2
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

Loading…