Pyridine → HCID 11439139, compound

Participants

Reaction Steps

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (47 mg, 0.21 mmol) in dichloromethane (2 mL) was added pyridine (40 μL, 0.50 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-benzo[b]thiophene [20] (30 mg, 0.20 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a dark brown solid (50 mg, 74%), single spot at Rf 0.58 (3:1 hexane:ethyl acetate). mp 108.5-109.0° C., HPLC purity 99% (tR 2.20 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.87 (1H, d, J=7.9 Hz), 7.70 (1H, d, J=8.7 Hz), 7.54-7.51 (2H, m), 7.44 (1H, d, J=5.4 Hz), 7.21 (1H, d, J=5.4 Hz), 7.16 (1H, t, J=7.9 Hz), 6.98 (1H, dd, J=8.7, 2.2 Hz), 6.73 (1H, s, N—H), 2.74 (3H, s). LCMS: 336.07. FAB-MS (MH+, C15H12ClNO2S2): calcd 336.9998, found 337.0004.

Provenance & Evidence