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

Temperature

150 °C

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)

1. customthe tube sealed
2. temperatureThe reaction was heated
3. temperatureThe reaction was cooled
4. filtrationbefore filtering through celite
5. customThe crude reaction mixture
6. customwas part-purified by column chromatography
7. washeluting with ethyl acetate
8. customhexane and the concentrated fractions further purified by preparative chromatography under acidic conditions

ORD record

ord-519c0baa932d419492e124d8fa6ef35c

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466201B2