4-(Trifluoromethoxy)benzylamine → 6-Bromo-N-(4-(trifluoromethoxy)benzyl)imidazo[1,2-a]pyridine-2-carboxamide

Me3Al (2.0M solution in toluene) (2.78 ml, 5.57 mmol) was added to a solution of ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate (500 mg, 1.85 mmol) in methylene chloride (10 ml) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. (4-(trifluoromethoxy)phenyl)methanamine (0.42 ml, 2.78 mmol) was added to the above mixture at room temperature. The reaction mixture was stirred at 50° C. for 20 hours. After cooling to room temperature, the reaction was quenched by 1N HCl solution (2-3 mL). The reaction mixture was partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride. The combined organic layer was washed with brine, then dried over anhydrous magnesium sulfate. After concentration, the residue was purified by flash chromatography (ethyl acetate:hexane=1:1) to give the title compound, 6-bromo-N-(4-(trifluoromethoxy)-benzyl)imidazo[1,2-a]pyridine-2-carboxamide, as a solid (440 mg, 57% yield).

1. stirringThe reaction mixture was stirred at 50° C. for 20 hours
2. temperatureAfter cooling to room temperature
3. customthe reaction was quenched by 1N HCl solution (2-3 mL)
4. customThe reaction mixture was partitioned between methylene chloride and water
5. extractionThe aqueous layer was extracted with methylene chloride
6. washThe combined organic layer was washed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationAfter concentration
9. customthe residue was purified by flash chromatography (ethyl acetate:hexane=1:1)

ORD record

ord-241852c7764647ba8e80861a5d529781

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09271969B2