Benzenesulfonyl chloride → HCID 11581951, compound

Participants

Reaction Steps

To a suspension of 1G (140 mg, 0.55 mmol) in CH3CN (4 mL) at RT was added DIPEA (153 μL, 0.88 mmol), followed by benzenesulfonyl chloride (84 μL, 0.66 mmol). After addition, the reaction was stirred at RT for 30 min. The reaction was diluted with H2O and extracted with EtOAc (20 mL×3). The combined organics were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel (12 g) column chromatography eluting with a gradient of EtOAc (20-100%) in hexane to give the title compound as a white solid (182 mg, 84%). LC/MS (method A): retention time=2.10 min, (M+H)+=394. 1H-NMR (DMSO6, 400 MHz): δ 8.25-8.36 (m, 3H), 7.85-7.90 (m, 2H), 7.52-7.70 (m, 3H), 7.15-7.30 (m, 5H), 6.93 (d, J=4 Hz, 1H), 5.04 (dd, J1=28.6 Hz, J2=16.3 Hz 2H), 4.35-4.46 (m, 1H), 2.90-3.15 (m, 2H).

Provenance & Evidence