Benzenesulfonyl chloride → 3-(1-Benzenesulfonyl-1H-indol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Participants

Reaction Steps

To a suspension of 18 (0.52 g, 1.82 mmol), tetrabutylammonium bisulfate (0.09 g, 0.27 mmol) and KOH (0.20 g, 3.63 mmol) in CH2Cl2 (15 mL) was stirred for 20 min, benzenesulfonyl chloride (0.35 ml, 2.72 mmol) was added and stirred at room temperature overnight. The reaction mixture was quenched with water extracted with CH2Cl2 (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:2) to afford 19 (0.42 g)

Provenance & Evidence