Reaction #1006002

Reaction equation

Me3Al

ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate

(4-(trifluoromethoxy)phenyl)methanamine

→

6-bromo-N-(4-(trifluoromethoxy)-benzyl)imidazo[1,2-a]pyridine-2-carboxamide

Solvents

methylene chloride

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred at 50° C. for 20 hours
2. 2
   TemperatureAfter cooling to room temperature
3. 3
   Otherthe reaction was quenched by 1N HCl solution (2-3 mL)
4. 4
   OtherThe reaction mixture was partitioned between methylene chloride and water
5. 5
   ExtractionThe aqueous layer was extracted with methylene chloride
6. 6
   WashThe combined organic layer was washed with brine
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   ConcentrationAfter concentration
9. 9
   Otherthe residue was purified by flash chromatography (ethyl acetate:hexane=1:1)

Procedure

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).

Source