反应详情

Tetrakis(triphenylphosphine)palladium(0) (0.076 g) was added to a deoxygenated mixture of 4-nitrophenyl 2-chloropyridine-3-sulphonate (0.69 g), 4-isobutylphenylboronic acid (0.47 g), potassium fluoride (0.38 g), toluene (15 ml) and water (2.5 ml) and the mixture was stirred and heated under reflux for 24 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2×80 ml). The organic extracts were washed with saturated sodium chloride solution and then combined and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with dichloromethane/hexane (1:1-1:0 v/v) then dichloromethane/hexane/ethyl acetate (10:9:1 v/v) through a silica gel Mega Bond Elut column followed by recrystallisation from ethyl acetate/hexane to give 4-nitrophenyl 2-(4-isobutylphenyl)pyridine-3-sulphonate (0.50 g), m.p. 123°-124° C.; 1H NMR (d6 -DMSO): 0.9 (d, 6 H), 1.9 (m, 1 H), 2.55 (d, 2 H), 7.2-7.3 (m, 4 H), 7.5 (d, 2 H), 7.7 (dd, 1 H), 8.2 (d, 2 H), 8.4 (dd, 1 H), 9.0 (dd, 1 H); mass spectrum (+ve FAB, NBA/DMSO): 413 (M+H)+.

1. temperatureheated
2. temperatureunder reflux for 24 hours
3. extractionthe mixture was extracted with ethyl acetate (2×80 ml)
4. washThe organic extracts were washed with saturated sodium chloride solution
5. dry with materialdried (MgSO4)
6. customVolatile material was removed by evaporation
7. customthe residue was purified by gradient elution with dichloromethane/hexane (1:1-1:0 v/v)
8. customdichloromethane/hexane/ethyl acetate (10:9:1 v/v) through a silica gel Mega Bond Elut column followed by recrystallisation from ethyl acetate/hexane