Sodium cyanoborohydride → HCID 86689834, compound

Participants

Reaction Steps

A microwave vial was charged with 1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone (1.50 g, 9.36 mmol), methanamine hydrochloride (8.85 g, 131.1 mol), NaBH3CN (765.0 mg, 12.18 mmol), and anhydrous EtOH (31 mL) and stirred while irradiated in a microwave (300 Watts) at 130° C. for 2 min. The resulting solid was filtered and rinsed well with EtOH. The filtrate was concentrated in vacuo. The crude product was redissolved in EtOAc and twice washed with 10% aq. NaOH, water and brine. The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was triturated with DCM, and the insoluble solid was filtered through a pad of Celite®. The filtrate was concentrated in vacuo and dried under high vacuum to afford N-methyl-1-(1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine as a solid: 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 7.66 (d, J=8.4 Hz, 1H), 7.45 (d, J=3.3 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 6.72 (d, J=3.3 Hz, 1H), 3.95 (q, J=6.7 Hz, 1H), 2.37 (s, 3H), 1.47 (d, J=6.7 Hz, 3H).

Provenance & Evidence