反应详情

温度

90 °C

1-Bromo-2-t-butylbenzenesulfonamide (22.4 g, 77 mmol) (Step A) and 4-methylphenyltrimethylstannane (39.35 g, 154 mmol 2eq.) were dissolved in 221 mL of dry dimethylformamide and the resulting solution treated with 2.71 g (38.6 mmol, 0.5eq) of bis(triphenylphosphine)palladium(II) chloride. The mixture was heated at 90° C. for 6 hours. The mixture was filtered through Celite and the filter cake was washed with ether. The combined organics were washed twice with water. The aqueous washings were combined and extracted with ether. The combined organics were washed with saturated aqueous sodium chloride then dried over magnesium sulfate, filtered and concentrated to dryness to yield the product which solidified on standing. Purification by preparative HPLC on silica, eluting with 10% ethyl acetate/hexane, gave 13.63 g (44.98 mmol, 58%) of the product as a yellow powder. 1H NMR (200 MHz, CDCl3): δ 1.09 (s, 9H), 2.50 (s, 3H), 3.64 (br s, 1H), 7.3-7.7 (m,7H), 8.13 (dd; 2, 8 Hz; 1H). FAB-MS: calculated for C17H21NO2S 303; found 304 (M+H, 3%).

1. filtrationThe mixture was filtered through Celite
2. washthe filter cake was washed with ether
3. washThe combined organics were washed twice with water
4. extractionextracted with ether
5. washThe combined organics were washed with saturated aqueous sodium chloride
6. dry with materialthen dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated to dryness
9. customto yield the product which
10. customPurification by preparative HPLC on silica
11. washeluting with 10% ethyl acetate/hexane