反应详情

To a slurry of 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methyl)azetidin-3-ol (0.100 g, 0.2 mmol) in 1 mL DCM under nitrogen at 0° C. was added (diethylamino)sulfur trifluoride (0.05 ml, 0.3 mmol). Upon consumption of starting material, the reaction was quenched with ice and 1 N NaOH. The reaction mixture was partitioned between water and DCM. The aqueous layer was extracted with DCM 3, and the combined cloudy organics were treated with a small amount of MeOH to give a solution, were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by RPHPLC, gradient, TFA/ACN in TFA/H2O provided material that was taken up in DCM and washed with saturated aq. NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo to give 2-(2-fluoro-4-((3-fluoroazetidin-1-yl)methyl)-phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine as a solid. MS (ESI) m/z: Calculated: 433.1; Observed: 434.1 (M++1).

1. customUpon consumption of starting material
2. customthe reaction was quenched with ice and 1 N NaOH
3. customThe reaction mixture was partitioned between water and DCM
4. extractionThe aqueous layer was extracted with DCM 3
5. additionthe combined cloudy organics were treated with a small amount of MeOH
6. customto give a solution
7. dry with materialwere dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification by RPHPLC, gradient, TFA/ACN in TFA/H2O provided material that
11. washwashed with saturated aq. NaHCO3
12. dry with materialdried over sodium sulfate
13. filtrationfiltered
14. concentrationconcentrated in vacuo