反应详情

温度

0 °C

Trimethylsilylmethylmagnesium chloride, 1.1 M solution in THF (15 mL) was added dropwise to a solution at 0° C. of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde (4.00 g, 11 mmol) in THF (80 mL) and the reaction mixture was stirred for 30 min at 0° C. The reaction mixture was quenched with 1 N aq. HCl and extracted with EtOAc twice, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in THF (100 mL), and cooled to 0° C. in ice bath. The slurry of potassium t-butoxide (2.4 g, 21 mmol) in THF (12 mL) was added slowly. At the end of the addition the reaction mixture was allowed to stir for 30 min at 0° C. At this time 1 N HCl was added and the mixture was extracted with EtOAc and the organic layer was dried over MgSO4. The residue was concentrated in vacuo and purified by silica gel chromatography to afford 2-(2-fluoro-4-vinylphenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine. MS (ESI) m/z: calculated: 372.1; Observed: 373.0 (M++1).

1. customThe reaction mixture was quenched with 1 N aq. HCl
2. extractionextracted with EtOAc twice
3. dry with materialdried over MgSO4
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was dissolved in THF (100 mL)
6. temperaturecooled to 0° C. in ice bath
7. additionAt the end of the addition the reaction mixture
8. stirringto stir for 30 min at 0° C
9. extractionthe mixture was extracted with EtOAc
10. dry with materialthe organic layer was dried over MgSO4
11. concentrationThe residue was concentrated in vacuo
12. custompurified by silica gel chromatography