反应详情

To a solution methyl-3-bromo-5-iodobenzoate (10.0 g, 29.3 mmol) and 5-methyl-2-pyridylzinc bromide (0.5 M in THF; 64.5 mL, 32.3 mmol) in tetrahydrofuran (84 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.70 g, 1.47 mmol). The reaction mixture was stirred at ambient temperature. After 6 h, saturated aqueous sodium bicarbonate was added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with sodium potassium tartrate tetrahydrate (2×), brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/ethyl acetate) gave the title compound. MS 306.0 (M).

1. extractionThe mixture was extracted with ethyl acetate (3×)
2. washThe combined organic extracts were washed with sodium potassium tartrate tetrahydrate (2×), brine
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/ethyl acetate)