反应 #1006002

反应方程式

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

溶剂

methylene chloride

反应条件

后处理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at 50° C. for 20 hours
2. 2
   温度After cooling to room temperature
3. 3
   其他the reaction was quenched by 1N HCl solution (2-3 mL)
4. 4
   其他The reaction mixture was partitioned between methylene chloride and water
5. 5
   萃取The aqueous layer was extracted with methylene chloride
6. 6
   洗涤The combined organic layer was washed with brine
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   浓缩After concentration
9. 9
   其他the residue was purified by flash chromatography (ethyl acetate:hexane=1:1)

实验过程

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).

来源