Sodium hydride → Methyl 1-(3-nitrobenzyl)indole-5-carboxylate

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Reaction Steps

Methyl indole-5-carboxylate (10 g) was dissolved in dry tetrahydrofuran (250 ml) and cooled in an ice-bath. To the stirred solution was added sodium hydride (60% suspension in oil) (2.57 g) in portions over 15 minutes. After stirring for a further 30 minutes, 3-nitrobenzyl bromide (11.55 g) in dry tetrahydrofuran (30 ml) was added dropwise over 20 minutes. Stirring was continued at 0° C. for 30 minutes, then at room temperature for 2 hours. Excess sodium hydride was destroyed by cautious addition of acetic acid, then the reaction mixture extracted from brine into ethyl acetate, dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. Recrystallisation from ethyl acetate/hexane afforded methyl 1-(3-nitrobenzyl)indole-5-carboxylate (m.p. 129°-130° C.).

Provenance & Evidence