Ammonium Chloride → 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

Participants

Reaction Steps

A mixture of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime (514 mg, 1.41 mmol), Zn power (4.6 g, 70.64 mmol), NH4Cl (1.5 g, 28.26 mmol) in MeOH (20 mL) and HOAc (4 mL) was heated at reflux overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was diluted with CH2Cl2 (200 mL) and aqueous ammonia (20 mL). The organic layer was separated, washed with H2O, dried (NaSO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with MeOH—CH2Cl2 (1:15) to afford 385 mg (78%) of 1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine as yellow oil. MS (ESI): m/z=350.0 [M+1]+.

Provenance & Evidence