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

HRID 40367

反応式

HRID 40367 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4788f5fe80d54912b65763985ef781b7
出典データセット
uspto-grants-2013_09
特許番号
US08524900B2

関連ノート

読み込み中…