反应详情

温度

70 °C

To a stirred suspension of (1R,2R,6S)-6-amino-2-[tert-butyl(dimethyl)silyl]oxy-2-methyl-cyclohexanol, 50e, (0.16 g, 0.62 mmol) in THF (8 mL) in a microwave sealed tube vessel was added 5-chloro-3-(5-fluoro-4-(methylsulfinyl)pyrimidin-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine, 1a, (0.29 g, 0.63 mmol) followed by N-ethyl-N-isopropyl-propan-2-amine (0.13 mL, 0.74 mmol). The resulting reaction mixture was capped and warmed to 70° C., stirred for 14 h. The reaction mixture was cooled to ambient temperature, added water (2 mL), concentrated under reduced pressure to remove THF. The crude product was diluted with ethyl acetate (25 mL), insoluble material (sulfone 1a) was removed by filtration. The organic layer was separated, washed with brine (2×5 mL), dried over Na2SO4, filter and concentrated under reduced pressure. The crude product was purified by silica-gel plug using 10-30% ethyl acetate in hexanes as eluant to afford 350 mg of (1R,2R,6S)-2-[tert-butyl(dimethyl)silyl]oxy-6-[[2-methyl[5-chloro-1-(p-tolylsulfonyl)-pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyridin-4-yl]amino]cyclohexanol (50f).

1. customsealed tube vessel
2. customThe resulting reaction mixture
3. customwas capped
4. temperatureThe reaction mixture was cooled to ambient temperature
5. concentrationconcentrated under reduced pressure
6. customto remove THF
7. additionThe crude product was diluted with ethyl acetate (25 mL), insoluble material (sulfone 1a)
8. customwas removed by filtration
9. customThe organic layer was separated
10. washwashed with brine (2×5 mL)
11. dry with materialdried over Na2SO4
12. filtrationfilter
13. concentrationconcentrated under reduced pressure
14. customThe crude product was purified by silica-gel plug