反应详情

6-bromo-3-iodopyrazolo[1,5-a]pyrimidine (1 eq) was mixed with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(2,2,2-trifluoro-1-pyridin-2-ylethyl)thiophene-2-carboxamide (1 eq, step B). Dioxane (10 mL) and 1M Na2CO3 (2 eq) were added. The mixture was evacuated and flushed with nitrogen under stirring, then Pd(Ph3P)4 (0.05 eq) was added in a flow of nitrogen. The temperature was brought to 90° C. The reaction mixture was stirred at this temperature overnight and concentrated. The residue was poured into a 5-fold excess of water. The mixture was extracted with chloroform. The organic layer was washed with brine, dried with MgSO4, and concentrated. The residue was purified by column chromatography (dichloromethane-methanol, 100:1) to give 4-(6-bromopyrazolo[1,5-a]pyrimidin-3-yl)-N-(2,2,2-trifluoro-1-pyridin-2-ylethyl)thiophene-2-carboxamide.

1. customThe mixture was evacuated
2. customflushed with nitrogen
3. customwas brought to 90° C
4. stirringThe reaction mixture was stirred at this temperature overnight
5. concentrationconcentrated
6. additionThe residue was poured into a 5-fold excess of water
7. extractionThe mixture was extracted with chloroform
8. washThe organic layer was washed with brine
9. dry with materialdried with MgSO4
10. concentrationconcentrated
11. customThe residue was purified by column chromatography (dichloromethane-methanol, 100:1)