反应详情

温度

-78 °C

To a solution of methyl 2-(quinolin-6-yl)propanoate (0.868 g, 4.03 mmol) in THF (1.1M, 3.7 mL) at −78° C. was added LiHMDS (1M in THF) (5.24 ml, 5.24 mmol). The reaction was stirred at −78° C. for ˜15 minutes, then to it was added a solution of N-fluorobenzenesulfonimide (1.40 g, 4.44 mmol) in THF (1.0M, 4.5 mL). The reaction was allowed to warm to −10° C. over 2 h. The reaction was filtered through a plug of Celite, washed with EtOAc and the filtrate was then concentrated in vacuo. The concentrated material was rediluted with EtOAc and washed with saturated NH4Cl solution. The aqueous layer was then extracted with EtOAc, and the organic layers were dried over MgSO4, filtered and concentrated in vacuo. The crude material was dissolved in minimal DCM and purified via MPLC (eluting with isocratic 40% EtOAc:Hexanes to yield methyl 2-fluoro-2-(quinolin-6-yl)propanoate (0.709 g, 75.4% yield) as a yellow oil. To synthesize the corresponding acid, methyl 2-fluoro-2-(quinolin-6-yl)propanoate was saponified in a method similar to that of 2-(quinolin-6-yl)propanoic acid.

1. temperatureto warm to −10° C. over 2 h
2. filtrationThe reaction was filtered through a plug of Celite
3. washwashed with EtOAc
4. concentrationthe filtrate was then concentrated in vacuo
5. additionThe concentrated material was rediluted with EtOAc
6. washwashed with saturated NH4Cl solution
7. extractionThe aqueous layer was then extracted with EtOAc
8. dry with materialthe organic layers were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. dissolutionThe crude material was dissolved in minimal DCM
12. custompurified via MPLC (
13. washeluting with isocratic 40% EtOAc