Hydrochloric Acid → HCID 66917718, compound

Participants

Reaction Steps

Thiophene-2-sulfonic acid ((E)-3-1H-indol-7-yl-acryloyl)-amide (I-4) To a round bottom flask (500 mL) which contained a solution of thiophenesulfonamide (1.05 g, 6 mmol), 4-dimethyaminopyridine (DMAP, 1.56 g, 13 mmol) and 1-[3-(dimethyamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 2.4 g, 13 mmol) in CH2Cl2 (150 mL) was added 3-(1H-indol-7-yl)-acrylic acid I-3 (1.2 g, 6 mmol) at rt. The mixture which resulted was allowed to stir at rt for 72 h, then was cooled to 5° C. and was acidified with addition of aq HCl (10%) until pH=1, which was followed by extraction of CH2Cl2/MeOH (9/1, 3×100 mL). The combined organic layers were dried over anhyd. Na2SO4 and the solvent was removed under reduced pressure to provide the crude product which was purified by flash chromatography (silica gel, CH2Cl2; CH2Cl2/EtOAc/hexane=1:10:20-1:20:10) to afford desired thiophene-2-sulfonic acid (3-1H-indol-7-yl-acryloyl)-amide I-4 (1.2 g, 56%) as a white solid. MS(ESI−)m/z(331.1, 100%). LCMS(ESI−)>95%.

Provenance & Evidence