反应详情

A vial was charged with 2′-bromo-7′-methoxyspiro[1,3-oxazole-4,9′-xanthen]-2-amine (90.0 mg, 249 μmol), 5-chloropicolinamide (59 mg, 374 μmol), cesium carbonate (244 mg, 748 μmol), copper(I) iodide (47 mg, 249 μmol), dioxane (2 mL), and N1,N2-dimethylethane-1,2-diamine (27 μl, 249 μmol). The vial was sealed under a blanket of Ar (g) and placed in a 110° C. oil bath for 5 days. The reaction mixture was then poured into a mixture of ammonium chloride solution (10 mL) and DCM (10 mL). The layers were separated, and the aqueous layer was extracted with DCM (2×5 mL). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was dissolved in DMSO and filtered, and the filtrate was purified by reverse-phase HPLC (10-90% CH3CN/H2O with 0.1% TFA). The fractions containing the desired product were poured into saturated sodium bicarbonate solution and extracted with DCM (3×). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated to give N-((4R)-2-amino-7′-methoxyspiro[1,3-oxazole-4,9′-xanthen]-2′-yl)-5-chloro-2-pyridinecarboxamide as a white solid. MS m/z=437.2 [M+H]+. Calc'd for C22H18ClN4O4: 437.1.

1. customplaced in a 110° C.
2. customfor 5 days
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with DCM (2×5 mL)
5. dry with materialThe combined organic extracts were dried over sodium sulfate
6. filtrationfiltered
7. customevaporated
8. dissolutionThe residue was dissolved in DMSO
9. filtrationfiltered
10. customthe filtrate was purified by reverse-phase HPLC (10-90% CH3CN/H2O with 0.1% TFA)
11. additionThe fractions containing the desired product
12. additionwere poured into saturated sodium bicarbonate solution
13. extractionextracted with DCM (3×)
14. dry with materialThe combined organic extracts were dried over sodium sulfate
15. filtrationfiltered
16. customevaporated