1. 4-Benzyloxyindole (1.12 g, 5.00 mmol) was dissolved in 10 mL of DMF at 0 °C and cooled to 0 °C. Sodium hydride (60 wt% dispersion, 220 mg, 5.50 mmol) was added slowly and reacted for 1 hour. Subsequently, benzenesulfonyl chloride (0.77 mL, 6.00 mmol) was added dropwise and the reaction continued for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate (EtOAc). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (25% ethyl acetate/hexane) to afford 4-(benzyloxy)-1-(phenylsulfonyl)-1H-indole (0.820 g, 2.26 mmol, 45% yield) as an off-white solid.1H NMR (399 MHz, chloroform-d) δppm: 7.79-7.89 (2H, m), 7.56-7.64 (1H m), 7.46-7.55 (2H, m), 7.28-7.46 (5H, m), 7.15-7.28 (2H, m), 6.99-7.14 (1H, m), 6.75-6.88 (1H, m), 6.62-6.74 (1H, m), 6.58 (1H, d, J=7.8Hz), 5.13 (2H, s).
