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

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Reaction Conditions

Reaction Steps

A mixture of 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime (0.75 mg, 2.16 mmol), zinc powder (7.06 g, 108 mmol), and NH4Cl (2.31 g, 43.2 mmol) in MeOH (30 mL) and HOAc (6 mL) was heated at 60° C. for 2 h. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was suspended in ammonia solution (50 mL) and extracted with DCM (50 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The crude was purified by SiO2 chromatography eluting with DCM/MeOH/Et3N to afford 0.5 g (97.7%) of 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine as a yellow solid. MS (ESI): m/z=334.3 [M+1]+.

Provenance & Evidence