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

To a mixture of 2-amino-5-bromo-pyridine o (11.6 mmol, 2.0 g) in ethanol (50 ml) was added 3-bromo-1,1,1-trifluoroacetone (2.1 equiv., 24.3 mmol, 4.64 g) and potassium carbonate (1.5 equiv., 17.3 mmol, 2.40 g). The mixture was heated at reflux for 24 hours and evaporated under reduced pressure. The residue was partitioned between a diluted aqueous sodium bicarbonate solution (100 ml) and dichloromethane (100 ml). The organic layer was dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with diisopropylether (20 ml) and filtered. The filtrate was evaporated under reduced pressure and the residue was triturated with petroleum ether (20 ml). The solids were isolated by filtration affording 6-bromo-2-trifluoromethyl-imidazo[1,2-a]pyridine p (3.0 g, yield=98%).

1. temperatureThe mixture was heated
2. temperatureat reflux for 24 hours
3. customevaporated under reduced pressure
4. customThe residue was partitioned between a diluted aqueous sodium bicarbonate solution (100 ml) and dichloromethane (100 ml)
5. dry with materialThe organic layer was dried (MgSO4)
6. customevaporated under reduced pressure
7. customThe residue was triturated with diisopropylether (20 ml)
8. filtrationfiltered
9. customThe filtrate was evaporated under reduced pressure
10. customthe residue was triturated with petroleum ether (20 ml)
11. customThe solids were isolated by filtration

ORD record

ord-83a3219ad3f647f28812c80adcea01a9

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07615639B2