Реакция #2258177

Уравнение реакции

water

methyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

cesium carbonate

1-bromo-4-fluorobutane

→

methyl 5-chloro-1-(4-fluorobutyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

Растворители

DMF

Условия реакции

Обработка

1. 1
   Температураto cool down to room temperature
2. 2
   Экстракцияthe product was extracted 3 times with DCM
3. 3
   СушкаThe combined organic layers were dried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated
6. 6
   Другоеto give the targeted product 11-d as a yellowish solid

Методика

To a solution of methyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate 11-c (2.9 g, 12.2 mmol) in DMF (50 mL) were added successively cesium carbonate (4 g, 12.2 mmol) and 1-bromo-4-fluorobutane (1.3 mL, 12.2 mmol). The resulting mixture was heated at 60° C. overnight. The reaction mixture was allowed to cool down to room temperature then poured into iced water and the product was extracted 3 times with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to give the targeted product 11-d as a yellowish solid. The product was used as such in the next step. m/z=313 (M+H)+, Cl pattern.

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