反应详情

A mixture of N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide (0.252 g) 4-methylbenzeneboronic acid (0.068 g), tetrakis(triphenylphosphine)palladium(0) (0.0115 g), toluene (2.5 ml), ethanol (1.25 ml) and 2M sodium carbonate solution (3.75 ml) was stirred vigorously and heated under reflux for 2 hours under an atmosphere of argon. Water (10 ml) was added and the mixture was extracted with ethyl acetate (2×10 ml). The combined extracts were washed with saturated sodium chloride solution (25 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:4 v/v), to give N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide (0.182 g); 1H NMR (DMSO-d6): 0.6 (d,6H), 1.55-1.75 (m,1H), 2.35 (s,3H), 2.5 (s,3H), 3.85 (d,2H), 3.95 (s,3H), 7.15-7.25 (m,4H), 7.35-7.45 (m,1H), 7.7-7.8 (m,2H), 8.15 (s,1H), 8.45-8.55 (m,1H); mass spectrum (+ve FAB, methanol/NBA): 470 (M+H)+.

1. temperatureheated
2. temperatureunder reflux for 2 hours under an atmosphere of argon
3. extractionthe mixture was extracted with ethyl acetate (2×10 ml)
4. washThe combined extracts were washed with saturated sodium chloride solution (25 ml)
5. dry with materialdried (MgSO4)
6. customVolatile material was removed by evaporation
7. customthe residue was purified by flash chromatography
8. washeluting with ethyl acetate/hexane (1:4 v/v)