反应详情

温度

115 °C

To a solution of 3-Bromo-4-cyclopropylmethoxy-pyridine (Example 42a, 4.1 g, 18.0 mmol) in a mixture of toluene (55 ml) and water (6.5 ml) was added potassium cyclopropyltrifluoroborate (CAN 1065010-87-8, 2.79 g, 18.9 mmol), palladium(II) acetate (80.7 mg, 360 μmol), butyldi-1-adamantylphosphine (CAN 321921-71-5, 193 mg, 539 μmol) and cesium carbonate (14.6 g, 44.9 mmol). The reaction mixture was stirred at 115° C. for 16 h, cooled down to room temperature and filtered through a pad of celite. The filtrate was poured into a separatory funnel, diluted with ethylacetate and extracted with water. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness. The crude was purified by flash chromatography on silica eluting with a heptane/(solution 3% triethylamine in ethylacetate) gradient to yield the title compound (2.67 gr, 78.5%) as a yellow oil. MS (ESI, m/z): 190.3 (M+H+).

1. temperaturecooled down to room temperature
2. filtrationfiltered through a pad of celite
3. additionThe filtrate was poured into a separatory funnel
4. additiondiluted with ethylacetate
5. extractionextracted with water
6. customThe organic phase was collected
7. dry with materialdried over sodium sulfate
8. customevaporated down to dryness
9. customThe crude was purified by flash chromatography on silica eluting with a heptane/(solution 3% triethylamine in ethylacetate) gradient