Ethyl Acetate → 4'-(2-carboxy-2-methylpropyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-biphenylsulphonamide

Participants

Reaction Steps

A solution of sodium carbonate (2.86 g) in water (4 ml) was added to a soultion of 2-iodo- N-(isobutoxycarbonyl)- N-(3-methoxy-5-methylpyrazin-2-yl)benzenesulphonamide (6.2 g), (2-carboxy-2-methylpropyl)benzeneboronic acid (3.0 g) and tetrakis(triphenylphosphine)palladium(O) (235 mg) in toluene (30 ml) and ethanol (20 ml). The mixture was stirred vigorously and heated under reflux for 18 hours under an atmosphere of argon. Water (100 ml) and ethyl acetate (100 ml) were added and the organic layer was separated. The organic phase was extracted with saturated sodium bicarbonate solution (50 ml) and the aqueous phases were combined. The solution was acidifed with 6M hydrochloric acid and extracted with ethyl acetate (3×50 ml). The extracts were washed with water (50 ml) and saturated sodium chloride solution (50 ml) and then dried (MgSO4). Volatile material was removed by evaporation and the residue was triturated with etherexane (1:1 v/v) to give 4'-(2-carboxy-2-methylpropyl)- N-(isobutoxycarbonyl)- N-(3-methoxy-5 -methylpyrazin-2-yl)-2-biphenylsulphonamide (2.25 g); 1H NMR (d6 -DMSO): 0.6 (d, 6H), 1.1 (s, 6H), 1.5-1.7 (m, 1H), 2.52 (s, 3H), 2.85 (s, 2H), 3.8 (d, 2H), 3.95 (s, 3H), 7.15 (d, 2H), 7.25 (d, 2H), 7.3-7.4 (m, 1H), 7.7-7.8 (m, 2H), 8.15 (s, 1H), 8.5-8.6 (m, 1H), 12.3 (s, 1H).

Provenance & Evidence