反应详情

温度

90 °C

7-Bromo-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (Example 50, Steps A-B; 0.0815 g, 0.171 mmol) was dissolved in 2 mL of 1:1 (DME:DMF). To this was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.0795 g, 0.257 mmol), Pd(dppf)Cl2 (5 mol %), and 2M aqueous sodium carbonate (256 μL, 0.513 mmol). Nitrogen was bubbled through the solution for 5 minutes and the reaction mixture was then heated to 90° C. for 16 hours. The reaction mixture was then diluted with EtOAc and the precipitate formed was filtered and the filtrate was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified by reverse phase chromatography to provided tert-butyl 4-(3-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)-5,6-dihydropyridine-1-(2H)-carboxylate, which was treated 4M HCl/dioxane to give the title product. MS (APCI), positive scan, m/z=478.2 (M+H).

1. customNitrogen was bubbled through the solution for 5 minutes
2. additionThe reaction mixture was then diluted with EtOAc
3. customthe precipitate formed
4. filtrationwas filtered
5. washthe filtrate was washed with water and brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe crude material was purified by reverse phase chromatography