27257-15-4

N-Methyl-d3-7-azaindole is a labeled reactant used in the preparation of blue fluorescent amino acids as in vivo building blocks for protein engineering.

GENERAL METHODS: Preparation of known compound 1a: 7-azaindole (2 g, 16.95 mmol) and anhydrous DMF (10 mL) were added to a dry round-bottomed flask equipped with a magnetic stirring bar under nitrogen atmosphere. The reaction mixture was cooled to 0 °C, 60% sodium hydride (1.2 eq.) was added in batches and stirring was continued for 1 h at this temperature. Subsequently, iodomethane (1.1 eq.) was added slowly and dropwise, keeping the reaction temperature at 0 °C and continuing to stir for 1 hour. Upon completion of the reaction, the reaction was quenched with ice-cold water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1-methyl-7-azaindole in quantitative yield.

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