This paper reports an one-pot method for the concomitant alkylation - oxidation (aromatization) of indolines, particularly effective to get easy access to N-alkyl-6-nitroindoles, which are useful platforms in medicinal chemistry. N-alkyl-6-nitroindoles are obtained in good yield (64-91%) by reaction at room temperature in non-degassed DMF of 6-nitroindoline, an alkyl halide, and NaH as base. The presence of NaH appears to be essential for a high yield conversion.
Laconde, G., Carato, P., Poupaert, J., Berthelot, P., Depreux, P., & Hénichart, J.-P. (2003). An expeditious one-pot synthesis of N-substituted 6-nitroindoles from indolines. Monatshefte für Chemie : an international journal of chemistry, 134(7), 1037-1043. https://doi.org/10.1007/s00706-003-0005-5 (Original work published 2003)