反应详情

Ethyl 1-[(6-bromopyridin-3-yl)methyl]-4-oxo-1,4-dihydrocinnoline-3-carboxylate [(Example 83, Step 1), 748 mg, 1.93 mmol] and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (682 mg, 3.28 mmol, 1.7 equiv) were suspended in tetrahydrofuran (15 mL) and treated with an aqueous solution (1.5 mL) of cesium carbonate (1.26 g, 3.85 mmol, 2 equiv). The mixture was sparged under nitrogen, treated with bis(tri-tert-butylphosphine)palladium(0) (197 mg, 0.385 mmol, 0.2 equiv) and placed in an oil bath preheated to 80° C. for 1 hour. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (75 mL, aqueous saturated) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate), providing the titled compound.

1. customThe mixture was sparged under nitrogen
2. customplaced in an oil bath
3. extractionextracted with ethyl acetate (2×100 mL)
4. dry with materialThe combined organic extracts were dried with sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate)