Реакция #84515

Уравнение реакции

diiodomethane

3-hydroxybenzonitrile

NaH

6-nitro-1H-indole

→

title compound

Выход 51.0%

3-((6-nitro-1H-indol-1-yl)methoxy)benzonitrile

Выход 51.0%

Растворители

DMF

DMF

DMF

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was then quenched with water
2. 2
   Фильтрацияfiltered
3. 3
   ЭкстракцияThe filtrate was extracted with DCM (30 mL×6)
4. 4
   Промывкаthe combined organic layers were washed with brine (50 mL×3)
5. 5
   Сушкаdried over anhydrous Na2SO4
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   ДругоеThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Методика

To a mixture of NaH (3.0 g, 75.0 mmol, 60%) in DMF (20 mL) were added a solution of 6-nitro-1H-indole (4.86 g, 30.0 mmol) in DMF (10 mL) and a solution of 3-hydroxybenzonitrile (3.57 g, 30.0 mmol) in DMF (10 mL) at 0° C. and the mixture was stirred at rt for 2 h. To the reaction mixture was added a solution of diiodomethane (7.5 mL, 90.0 mmol) in DMF (10 mL) slowly without light and the mixture was stirred at rt for 20 h. The mixture was then quenched with water and filtered. The filtrate was extracted with DCM (30 mL×6) and the combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (4.47 g, 51%).

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