Cesium carbonate → 2-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)-5-methyl-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-one

A 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 313d (300 mg, 1.8 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (482 mg, 1.8 mmol), cesium carbonate (1.17 g, 3.6 mmol), and 1,4-dioxane (20 mL). After bubbling nitrogen through the suspension for 10 minutes, xantphos (104 mg, 0.18 mmol) and tris(dibenzylideneacetone)dipalladium(0) (82 mg, 0.090 mmol) were added. The system was subjected to three cycles of vacuum/argon flush and heated at reflux for 5 h. It was then cooled to room temperature and filtered. The solid was washed with dichloromethane (2×30 m). The combined filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (80/1 to 30/1) to afford 313e (390 mg, 61%) as a yellow solid.

1. customA 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
2. customAfter bubbling nitrogen through the suspension for 10 minutes
3. customflush
4. temperatureheated
5. temperatureat reflux for 5 h
6. filtrationfiltered
7. washThe solid was washed with dichloromethane (2×30 m)
8. concentrationThe combined filtrate was concentrated under reduced pressure
9. customThe residue was purified by silica-gel column chromatography
10. washeluting with dichloromethane/methanol (80/1 to 30/1)

ORD 기록

ord-9cf2a744a9814a22adcd885926423f92

출처 데이터셋

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08716274B2