反应详情

温度

70 °C

1.025 g 3-(1-(tert-butyldimethylsilyloxy)vinyl)-2-(pyridin-2-ylethynyl)pyridine was dissolved in 100 mL dimethoxyethane and 126 mg of trifluormethanesulfonic acid silver salt added and stirred 7 h at 70° C. The mixture is diluted with DCM and extracted with saturated NaHCO3 solution (3×). The organic phase was dried (MgSO4) and concentrated in vacuo. The residual mixture was dissolved in 10 mL THF, 1.2 mL of tertbutylammoniumfluoride in THF (1N) was added and the mixture stirred for 2 h at 25° C. The mixture was diluted with DCM and extracted with water (1×) and the organic phase concentrated in vacuo and purified via FCC (100 g SiO2, DCM→DCM 93:7) to yield 165 mg of 7-(pyridin-2-yl)quinolin-5-ol 6.3 as solid. HPLC-MS: Rt=0.78 min (method E), M+H=223.

1. extractionextracted with saturated NaHCO3 solution (3×)
2. dry with materialThe organic phase was dried (MgSO4)
3. concentrationconcentrated in vacuo
4. dissolutionThe residual mixture was dissolved in 10 mL THF
5. addition1.2 mL of tertbutylammoniumfluoride in THF (1N) was added
6. stirringthe mixture stirred for 2 h at 25° C
7. additionThe mixture was diluted with DCM
8. extractionextracted with water (1×)
9. concentrationthe organic phase concentrated in vacuo
10. custompurified via FCC (100 g SiO2, DCM→DCM 93:7)