2-amino-N-(2-hydroxyethyl)benzenesulfonamide

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-Amino-N-(2-hydroxyethyl)-benzene sulfonamide (160 mg, 0.74 mmol), 1,3,5-trichloro-2-bromobenzene (241 mg, 0.93 mmol), K2CO3 (256 mg, 1.85 mmol) and xantphos (43 mg, 0.074 mmol) in acetonitrile (2 ml) under nitrogen in a microwave tube was added Pd2dba3 (34 mg, 0.037 mmol) in one portion and the tube sealed. The reaction was heated with stirring in a microwave at 160° C. for 120 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 (49.0 mg, 17%); δH (400 MHz, DMSO) 7.83 (3H, m), 7.75+7.45 (1H, d), 7.59+7.10 (1H, s), 7.55+7.38 (1H, t), 7.16+6.95 (1H, t), 7.10+6.40 (1H, d), 4.73 (1H, m), 3.35 (2H, m) and 2.83 (2H, m); LCMS Rt=7.92 min, m/z (ES+) 397 (M+H). the tube sealed The reaction was heated 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-(2-Hydroxyethyl)-2-nitrobenzene sulfonamide (1.25 g, 5.08 mmol) was dissolved in methanol (50 ml) and placed under an atmosphere of nitrogen prior to the addition of 10% Pd/C (10 Wt %, 125 mg) in one portion. The reaction was evacuated, placed under an atmosphere of hydrogen (1 bar) and stirred vigorously overnight. The reaction was filtered through celite and the filtrate was concentrated in vacuo to afford the named product (0.88 g, 80%); LCMS Rt=2.05 min, m/z (ES+) 217 (M+H). The reaction was evacuated The reaction was filtered through celite the filtrate was concentrated in vacuo