反应详情

Oxone (701 mg, 1.14 mmol) in H2O (12 mL) was added to 5-chloro-N-{1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (Example 5; 355 mg, 0.86 mmol) in MeOH (12 mL) and stirred for 18 hours. The mixture was diluted with EtOAc (100 mL) washed with saturated NaHCO3 (20 mL), dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:THF (3:2) then DCM:MeOH (4:1)) to give 2 yellow solids. Each solid was triturated with refluxing Et2O (25 mL) and the solids filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford 5-chloro-N-{1-[2-(methylsulphinyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (125 mg, 34%) and 5-chloro-N-{1-[2-(methylsulphonyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (95 mg, 25%) as white solids.

1. washwashed with saturated NaHCO3 (20 mL)
2. dry with materialdried (Na2SO4)
3. filtrationfiltered
4. customevaporated
5. customThe residue was purified by column chromatography (DCM to DCM:THF (3:2)
6. customDCM:MeOH (4:1)) to give 2 yellow solids
7. customEach solid was triturated with refluxing Et2O (25 mL)
8. filtrationthe solids filtered
9. washwashed with Et2O (25 mL)