Cesium carbonate → 8-Chloro-3-(2,2,2-trifluoroethoxy)-1,5-naphthyridine

HRID 40367

반응식

HRID 40367 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:25][C:26]([F:29])([F:28])[F:27])(=O)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][CH2:25][C:26]([F:29])([F:28])[F:27])=[CH:7]2

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 1357435768-Chloro-1,5-naphthyridin-3-ol

생성물 1

HCID 576912048-Chloro-3-(2,2,2-trifluoroethoxy)-1,5-naphthyridine수율 56.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

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][email protected] minutes. Calc'd for C10H6ClF3N2O=262.6.

후처리

  1. customVessel sealed
  2. customReaction
  3. customQuench with water
  4. additiondilute with aqueous sodium bicarbonate solution and dichloromethane
  5. customLayers separated
  6. customorganic layer collected
  7. dry with materialdried over sodium sulfate
  8. concentrationThis was concentrated
  9. customto afford yellow oil
  10. customwhich was purified by ISCO silica gel chromatography (20-40% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-4788f5fe80d54912b65763985ef781b7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524900B2

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