Synthesis
General procedure for the synthesis of p-bromomethylbenzenesulfonamide from 4-bromomethylbenzenesulfonyl chloride:
4.1 Synthesis of acetylsulfonamide (SZ2TA1): ammonia was passed into a solution of compound 1 (1 g, 3.7 mmol) in dichloromethane (DCM, 100 mL) at 0°C for 10 min. Subsequently, brine (20 mL) was added for quenching. The organic phase was separated, dried over anhydrous sodium sulfate, and concentrated. Purification by fast chromatography (eluent ratio: hexane:EtOAc = 2:1) afforded product 17 (900 mg, 96.8% yield).
1H-NMR (250 MHz, acetone-d6) δ: 7.91 (d, J = 10.0 Hz, 2H), 7.67 (d, J = 10.0 Hz, 2H), 6.63 (bs, 2H), 4.74 (s, 2H) ppm.
References
[1] ChemMedChem, 2011, vol. 6, # 5, p. 816 - 825
[2] Journal of the American Chemical Society, 2008, vol. 130, # 42, p. 13820 - 13821
[3] Patent: WO2012/21486, 2012, A2. Location in patent: Page/Page column 113; 114
[4] Patent: WO2012/21486, 2012, A2. Location in patent: Page/Page column 96; 97
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 5, p. 462 - 467
