反应详情

To a slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-benzylthiazolo[5,4-b]pyridine (2.28 g, 5.6 mmol) in 40 mL DMF under argon was added lithium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (7.0 mL, 7.0 mmol). A very deep blue solution resulted. After 2 min, allyl iodide (0.77 mL, 8.4 mmol) was added via syringe and the reaction became brown. After 5 min, sat'd aq. NH4Cl was added and the reaction partitioned between water and EA. The organic was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was sonicated in MTBE, filtered, and dried to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylbut-3-enyl)thiazolo[5,4-b]pyridine as a yellow solid. MS (ESI) m/z: Calculated: 446.2; Observed: 447.1 (M++1).

1. customA very deep blue solution resulted
2. waitAfter 5 min
3. additionwas added
4. customthe reaction partitioned between water and EA
5. washThe organic was washed with water, brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting material was sonicated in MTBE
10. filtrationfiltered
11. customdried