反应详情

温度

95 °C

A mixture of 1.356 g (3.60 mmol) of 5-bromo-3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine, 3.445 g, (16.80 mmol) of 3-pyridineboronic acid pinacol ester and 0.457 g (0.560 mmol) of 1,1′bis(diphenylphosphino)ferrocenepalladium (II) chloride and 7.2 ml of 1.0 M of Cesium Carbonate in water in 60 ml of Acetonitrile was degassed an heated in a sealed glass vial at 95° C. for 2 hours. The mixture was filtered through Celite and the filtrate concentrated in vacuum. The residue was redissolved in dichloromethane, the organic layer washed with water, brine, dried over MgSO4 and concentrated. The crude residue was purified on a 80 g silica gel column eluting with 3-4% of methanol in dichloromethane. Pooled fractions were concentrated. The residue was triturated with 7 ml of cold methanol and filtered to give 3-(6-Fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine. Yield 1.147 g (85%). ESI MS m/z=376.1 (M+1)

1. customwas degassed
2. filtrationThe mixture was filtered through Celite
3. concentrationthe filtrate concentrated in vacuum
4. dissolutionThe residue was redissolved in dichloromethane
5. washthe organic layer washed with water, brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe crude residue was purified on a 80 g silica gel column
9. washeluting with 3-4% of methanol in dichloromethane
10. concentrationPooled fractions were concentrated
11. customThe residue was triturated with 7 ml of cold methanol
12. filtrationfiltered