Реакция #43546

Уравнение реакции

water

5-Fluoro-1H-indole-2,3-dione

sodium hydride

p-methoxybenzyl chloride

→

5-Fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione

Выход 80.0%

Растворители

DMF

DMF

ethyl acetate hexane

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe solution was then stirred ca 2 hours
2. 2
   Экстракцияfollowed by extraction into ethyl acetate
3. 3
   ПромывкаThe organic layer was washed twice with water
4. 4
   Сушкаdried over MgSO4

Методика

5-Fluoro-1H-indole-2,3-dione (956 mg, 5.79 mmol, 1 eq) was added as a solution in dry DMF to a stirred slurry of sodium hydride (278 mg, 11.6 mmol, 2 eq) in dry DMF drop wise over 15 minutes under an inert atmosphere with adequate pressure release to accommodate H2 evolution. The resulting mixture was stirred for 1 hour and p-methoxybenzyl chloride was added via syringe to the reaction. The solution was then stirred ca 2 hours and worked up by addition of water followed by extraction into ethyl acetate. The organic layer was washed twice with water and then dried over MgSO4. Column chromatography with ethyl acetate/hexane afforded 5-Fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione as a red solid (1.3 g, 80% yield). 1H NMR (CDCl3) δ (ppm): 7.3-7.24 (m, 3H), 7.20 (td, J=8.7, 2.7 Hz, 1H), 6.9-6.86 (m, 2H), 6.76 (dd, J=8.6, 3.6 Hz, 1H), 3.81 (s, 2H), 3.78 (s, 3H). LC/MS=286.1 (M+1).

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