Ammonium Chloride → HCID 58528795, compound

Participants

Reaction Steps

A mixture of N-(5-bromo-pyridin-2-yl)-4-fluoro-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-2-nitro-benzamide (1.42 g, 3.14 mmol). 325 mesh iron dust (7.1 g, 127 mmol), 6 mL of 4 M aqueous NH4Cl and 60 mL of isopropanol were mechanically stirred at 85° C. for 4 h, then slurried hot with Celite and filtered. The filtrate was diluted with EtOAc, washed with brine, dried (MgSO4) and evaporated. The residue obtained was triturated in boiling methanol. After cooling, the resulting solid was collected by filtration and dried under high vacuum to provide 692 mg (52%) of the title compound as a light-green solid. 1H NMR (500 MHz, DMSO-d6): δ 3.67 (s, 3H), 6.58 (d, 1H, J=12 Hz), 6.89 (s, 1H), 6.95 (br s, 2H), 7.26 (s, 1H). 7.99 (d, 1H, J=8 Hz), 8.03 (d, 1H, J=8 Hz), 8.04 (d, 1H, J=8 Hz), 8.50 (s, 1H). 10.86 (s, 1H); LCMS (m/z): 422/424 [C16H13BrFN5OS+H]+.

Provenance & Evidence