تفاعل #1006002

معادلة التفاعل

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

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر