Potassium Carbonate → N-(2-Hydroxyethyl)-C-[3-(2,4,6-trichlorophenylamino)-phenyl]-methane sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of C-(3-Aminophenyl)-N-(2-hydroxyethyl)-methanesulfonamide (200 mg, 0.87 mmol), 1,3,5-trichloro-2-bromobenzene (283 mg, 1.09 mmol), K2CO3 (300 mg, 2.17 mmol) and XantPhos (50 mg, 0.09 mmol) in 1,4-dioxane (2 ml) under nitrogen in a microwave tube was added Pd2dba3 (40 mg, 0.04 mmol) in one portion and the tube sealed. The reaction was heated with stirring in a microwave at 150° C. for 60 minutes. The reaction was cooled before filtering through celite. The crude reaction mixture was part-purified by column chromatography eluting with ethyl acetate:hexane and the concentrated fractions further purified by preparative chromatography under acidic conditions to afford the named product (17.8 mg, 5%); 6H (400 MHz, DMSO) 8.00 (1H, s), 7.76 (2H, s), 7.12 (1H, t), 6.99 (1H, t), 6.76 (1H, d), 6.62 (1H, s), 6.48 (1H, d), 4.69 (1H, brs), 4.21 (2H, s), 3.39 (2H, m) and 2.93 (2H, q); LCMS Rt=3.83 min, m/z (ES−) 409 (M−H).

Provenance & Evidence