反应详情

温度

95 °C

To a solution of 6-bromo-3-(2-trimethysilylethoxymethyl)-3H-imidazo-[4,5-b]-pyridine (1.3 g, 4 mmol) and bis(triphenylphosphine)-palladium (II) chloride in DMF (12 mL) was added tributylvinyl tin (2.14 g, 6.7 mmol). The reaction vessel was evacuated-purged (N2) several times followed by heating to 95° C. for 15 h. After cooling, the crude reaction mixture was filtered through a pad of celite® and eluted with ethyl ether. The ethereal mixture was washed several times with saturated KF, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel using a gradient elution of ethyl acetate/hexanes (10, 20, 30 to 40%) which provided 1.06 g of the title compound (97% yield).

1. customThe reaction vessel was evacuated-purged (N2) several times
2. temperatureAfter cooling
3. customthe crude reaction mixture
4. filtrationwas filtered through a pad of celite®
5. washeluted with ethyl ether
6. washThe ethereal mixture was washed several times with saturated KF, brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude residue was purified by flash chromatography on silica gel using
11. washa gradient elution of ethyl acetate/hexanes (10, 20, 30 to 40%) which