HCID 58531544, compound → HCID 58531635, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxy-N-((4′-nitrobiphenyl-3-yl)-methyl)benzenesulfonamide (0.2 g, 0.4 mmol) and iron (0.1 g, 2.1 mmol) in acetic acid (5 mL) was heated at 70° C., under a nitrogen atmosphere. After 40 minutes, the reaction mixture was cooled to room temperature and filtered through a pad of Celite®. The pad was thoroughly rinsed with EtOAc followed by CHCl3. The combined filtrates were concentrated in vacuo. The crude product was dissolved in CHCl3 then passed through a RediSep normal phase silica flash column (12 g) eluting with CHCl3. The appropriate fractions were concentrated in vacuo to afford the title compound (0.18 g, 84%) as an off-white solid. 1H NMR (DMSO-d6) δ 7.77 (d, J=2.2 Hz, 1H), 7.58 (d, J=2.7 Hz, 1H), 7.34 (d, J=7.7 Hz, 1H), 7.24-7.03 (m, 8H), 6.93 (d, J=7.7 Hz, 1H), 6.63-6.58 (m, 2H), 4.46 (s, 2H), 4.43 (s, 2H). MS (ESI): 531.0 (M+H)+.

Provenance & Evidence