반응 #68645

반응 방정식

8-chloro-1,5-naphthyridin-3-ol

cesium carbonate

2,2,2-trifluoroethyl trifluoromethanesulfonate

→

8-chloro-3-(2,2,2-trifluoroethoxy)-1,5-naphthyridine

수율 56.3%

용매

DMF

반응 조건

후처리

1. 1
   기타Vessel sealed
2. 2
   기타Reaction
3. 3
   기타Quench with water
4. 4
   workup.ADDITIONdilute with aqueous sodium bicarbonate solution and dichloromethane
5. 5
   기타Layers separated
6. 6
   기타organic layer collected
7. 7
   건조dried over sodium sulfate
8. 8
   농축This was concentrated
9. 9
   기타to afford yellow oil
10. 10
    기타which was purified by ISCO silica gel chromatography (20-40% EtOAc/Hexanes)

실험 절차

A resealable pressure bottle was charged with 8-chloro-1,5-naphthyridin-3-ol (80 mg, 0.44 mmol), cesium carbonate (433 mg, 1.3 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (360 mg, 1.55 mmol), and DMF (0.9 ml). Vessel sealed and placed in a pre-heated at 50° C. oil bath. Reaction allowed to stir at this temperature for 45 minutes. LC/MS shows complete conversion. Quench with water, dilute with aqueous sodium bicarbonate solution and dichloromethane. Layers separated, organic layer collected and dried over sodium sulfate. This was concentrated to afford yellow oil; which was purified by ISCO silica gel chromatography (20-40% EtOAc/Hexanes) to afford 8-chloro-3-(2,2,2-trifluoroethoxy)-1,5-naphthyridine (65 mg, 56% yield). MS [M+H]=263.0@1.89 minutes. Calc'd for C10H6ClF3N2O=262.6.

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