5-Nitroindole → 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

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Reaction Steps

5-Nitroindole (2.6 g) was dissolved in anhydrous MeOH (100 ml), followed by N-methyl-4-piperidone (5 g) and NaOMe powder (5 g). The mixture was heated to reflux under N2 overnight. The mixture was concentrated in vacuo. The crude was partitioned between saturated NaHCO3 solution and EtOAc, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford a yellow solid. This solid was washed with EtOAc (5 mL) and MeOH (2 ml) to afford the title compound as a bright yellow solid. MS: 258 (M+1). Calc'd. for C14H15N3O2−257.29.

Provenance & Evidence