反应详情

To a solution of 2,2,2-trifluoro-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo-[5,4-b]pyridine-2-yl)phenyl)ethanol (1.15 g, 2.6 mmol) in 25 mL DCM under nitrogen was added Dess-Martin Periodinane (2.0 g, 4.7 mmol) in one portion. The reaction mixture was allowed to stir for 3 h. The reaction mixture was quenched with sat'd aq. Sodium thiosulfate (2 mL) and 25 mL sat'd aq. Sodium bicarbonate and allowed to stir rapidly for 30 min. The organic layer was separated and the aq. Layer was extracted with DCM, combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give a yellow foam. The material was treated with DCM and passed through a Redi-Sep® pre-packed silica gel column (40 g) using 0-60% EtOAc/hexane. The product-containing fractions were concentrated to afford 2,2,2-trifluoro-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)phenyl)ethanone as a yellowish foam. The foam was treated with hexanes and concentrated in vacuo a few times to give a nice light yellow solid. MS (ESI) m/z: calculated: 442.1; Observed: 461.0 (M++H2O+1).

1. customThe reaction mixture was quenched with sat'd aq. Sodium thiosulfate (2 mL) and 25 mL
2. stirringto stir rapidly for 30 min
3. customThe organic layer was separated
4. extractionthe aq. Layer was extracted with DCM
5. dry with materialcombined organics were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a yellow foam
9. concentrationThe product-containing fractions were concentrated