6-Bromo-5-methyl-2-pentafluoroethyl-2,3-dihydroimidazo[1,2-a]pyridin-2-ol hydrobromide → 6-Bromo-5-methyl-2-pentafluoroethylimidazo[1,2-a]pyridine

HRID 1775289Notes

Reaction equation

HRID 1775289 reaction equation
Br.[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH2:10][C:11]([C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])(O)[N:12]=2)[C:8]=1[CH3:9]>C(O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:10]=[C:11]([C:14]([F:19])([F:20])[C:15]([F:18])([F:17])[F:16])[N:12]=2)[C:8]=1[CH3:9]

Participants

3

Reactant 1

HCID 1180352206-Bromo-5-methyl-2-pentafluoroethyl-2,3-dihydroimidazo[1,2-a]pyridin-2-ol hydrobromide

Product 1

HCID 1180350376-Bromo-5-methyl-2-pentafluoroethylimidazo[1,2-a]pyridineYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.95 g of 6-bromo-5-methyl-2-pentafluoroethyl-2,3-dihydroimidazo[1,2-a]pyridin-2-ol hydrobromide and 20 ml of ethanol was stirred under heat-reflux for 1 day. The cooled reaction mixture was concentrated under reduced pressure, then water and a saturated aqueous sodium bicarbonate solution were added, and the precipitated solid was taken by filtration. The resulting solid was dried to obtain 2.92 g of 6-bromo-5-methyl-2-pentafluoroethylimidazo[1,2-a]pyridine.

Workup

  1. temperatureunder heat-reflux for 1 day
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. additionwater and a saturated aqueous sodium bicarbonate solution were added
  5. filtrationthe precipitated solid was taken by filtration
  6. customThe resulting solid was dried

Sources & evidence

ORD record
ord-85f9058d7e4349698004cf1115f513b7
Source dataset
uspto-grants-2016_02
Patent number
US09260436B2

Reaction notes

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