Potassium Carbonate → HCID 21186226, compound

Participants

Reaction Steps

A mixture of 2-(4-hydroxyphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.472 g), methyl 2-bromopropionate (217mg) and potassium carbonate (166 mg) in acetone (20 ml) was heated under reflux for 15 hours. Volatile material was removed by evaporation and water (25 ml) was added to the residue. The mixture was extracted with ethyl acetate (25 ml) and the extracts were washed with 2M sodium hydroxide solution (10 ml) and water (20 ml). The solution was dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), to give N-(isobutoxycarbonyl)-2-(4-[1-(methoxycarbonyl)ethoxy]phenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.32 g); 1H NMR (DMSO-d6): 0.6 (d, 6 H), 1.5-1.7 (m, 4 H), 2.5 (s, 3 H), 3.7 (s, 3 H), 3.8 (d, 2 H), 4.0 (s, 3 H), 5.1 (q, 1 H), 6.95 (d, 2 H), 7.5 (d, 2 H), 7.7-7.8 (m, 1 H), 8.2 (s, 1 H), 8.85 (d, 1 H), 8.9 (d, 1 H).

Provenance & Evidence