反应详情

A vial was charged with (R)-2′-bromo-7′-(neopentyloxy)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (55.6 mg, 0.133 mmol), tetrakis(triphenylphosphine)palladium (0) (15.40 mg, 0.013 mmol), 2-(tributylstannyl)pyrazine (148 mg, 0.400 mmol), and dioxane (0.7 mL). The vial was sealed under a blanket of Ar gas and placed in a 100° C. oil for 16 h. The mixture was then cooled and filtered through celite. The filtrate was evaporated, and the residue was purified by chromatography on a 12-g Redi-Sep column, eluting with 0-10% MeOH/DCM to give a brown oil. This oil was dissolved in MeOH and filtered through a 2 micron filter, then purified further by reverse-phase HPLC (10-90% CH3CN/H2O with 0.1% TFA). The product containing fractions were combined in saturated aqueous sodium bicarbonate solution with the aid of MeOH. The mixture was extracted with DCM (2×), and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated to give (S)-2′-(neopentyloxy)-7′-(pyrazin-2-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as a white solid. MS m/z=417.2 [M+H]+. Calc'd for C24H25N4O3: 417.19.

1. customThe vial was sealed under a blanket of Ar gas
2. customplaced in a 100° C.
3. customfor 16 h
4. temperatureThe mixture was then cooled
5. filtrationfiltered through celite
6. customThe filtrate was evaporated
7. customthe residue was purified by chromatography on a 12-g Redi-Sep column
8. washeluting with 0-10% MeOH/DCM
9. customto give a brown oil
10. filtrationfiltered through a 2 micron
11. filtrationfilter
12. custompurified further by reverse-phase HPLC (10-90% CH3CN/H2O with 0.1% TFA)
13. additionThe product containing fractions
14. extractionThe mixture was extracted with DCM (2×)
15. dry with materialthe combined organic extracts were dried over sodium sulfate
16. filtrationfiltered
17. customevaporated