Реакция #8879

Уравнение реакции

product

5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2-oxopropoxy)-nicotinonitrile

sodium ethoxide

→

title compound

1-[3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl]ethanone

Растворители

ethanol

Условия реакции

Обработка

1. 1
   Температураat reflux for 1 hour
2. 2
   Другоеquenched with saturated NaHCO3 solution
3. 3
   ДругоеThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
4. 4
   ПромывкаThe organic layer was washed twice with saturated NaHCO3 solution, brine
5. 5
   Сушкаdried (Na2SO4)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеPurification by MPLC (silica gel; 0% to 20% ethyl acetate-hexane gradient)

Методика

A solution of the product from Step A (0.126 g; 0.292 mmol) in ethanol (4 mL) was treated with sodium ethoxide (0.040 g; 0.584 mmol) and stirred at reflux for 1 hour. The reaction was allowed to cool to room temperature and quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate-hexane gradient) gave the title compound. HPLC/MS: 430.9 (M+1), 432.9 (M+3); Rt=4.04 min.

Источник