反応 #1006002

反応方程式

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

溶媒

methylene chloride

反応条件

後処理

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
   その他the reaction was quenched by 1N HCl solution (2-3 mL)
4. 4
   その他The reaction mixture was partitioned between methylene chloride and water
5. 5
   抽出The aqueous layer was extracted with methylene chloride
6. 6
   洗浄The combined organic layer was washed with brine
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   濃縮After concentration
9. 9
   その他the residue was purified by flash chromatography (ethyl acetate:hexane=1:1)

実験手順

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).

出典