Toluene → HCID 23226635, compound

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (0.022 g) was added to a deoxygenated mixture of 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl) ethoxymethyl]pyridine-3-sulphonamide (0.405 g), 4-methylthiophenylboronic acid (obtained by the procedure described in Tetrahedron Lett., 1993, 34, 8237) (0.148 g), toluene (4.5 ml), ethanol (2.5 ml) and 2M sodium carbonate solution (7 ml) and the mixture was stirred and heated under reflux for 18 hours. Water was added and the mixture was extracted three times with ethyl acetate. The organic extracts were combined, washed with saturated sodium chloride solution and then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 0-35% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-methylthiophenyl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide (0.415 g) as an oil; 1H NMR (CDCl3): 0.0 (s, 9 H), 0.8 (t, 2 H), 2.5 (s, 3 H), 2.55 (s, 3 H), 3.6 (t, 2 H), 3.9 (s, 3 H), 4.8 (s, 2 H), 7.3-7.5 (m, 3 H), 7.6-7.7 (m, 2 H), 7.8 (s, 1 H), 8.7 (dd, 1 H), 8.8 (dd, 1 H); mass spectrum (+ve ESP): 533 (M+H)+.

Provenance & Evidence