Potassium Carbonate → n-(2-Hydroxyethyl)-3-(2,4,6-trichlorophenylamino)-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-Amino-N-(2-hydroxyethyl)-benzene sulfonamide (200 mg, 0.93 mmol), 1,3,5-trichloro-2-bromobenzene (301 mg, 1.16 mmol), K2CO3 (319 mg, 2.31 mmol) and XantPhos (54 mg, 0.093 mmol) in acetonitrile (2 ml) under nitrogen in a microwave tube was added Pd2dba3 (43 mg, 0.047 mmol) in one portion and the tube sealed. The reaction was heated with stirring in a microwave at 150° C. for 45 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 (96.3 mg, 26%); 6H (400 MHz, DMSO) 8.45 (1H, s), 7.82 (2H, s), 7.54 (1H, t), 7.33 (1H, t), 7.13 (1H, d), 6.93 (1H, s), 6.76 (1H, d), 4.70 (1H, brs), 3.35 (2H, m) and 2.75 (2H, q); LCMS Rt=3.79 min, m/z (ES−) 392 (M−H)

Provenance & Evidence