Ammonium Chloride → (+/-)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime (1.29 g, 3.92 mmol), zinc (2.55 g, 39.2 mmol), and NH4Cl (2.10 mg, 39.2 mmol) in MeOH (5 mL) and HOAc (3 mL) was stirred at 80° C. for 4 h. The mixture was cooled to RT and the solid filtered. The filtrate was concentrated under reduced pressure. To the residue was added ammonia solution (50 mL) and the reaction mixture was extracted with DCM (3×50 mL). The combined organic extracts were concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (15:1:0.2) to afford 1.08 g (87.4%) (±)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine as a yellow solid: MS (ESI) m/z: 316.2 [M+1]+.

Provenance & Evidence