Chlorotrimethylsilane → 1-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole

Temperatur

-78 °C

To a solution of 4,5-dibromo-1-ethyl-2-naphthalen-1-yl-1H-imidazole (6.55 g, 17.2 mmol) in anhydrous THF (150 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 11.8 ml, 19 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, and TMSCl (2.05 g, 19 mmol, 1.1 eq.) is added. The resulting solution is stirred at −78° C. After 1 hr, n-BuLi in hexane (1.6 M, 11.8 ml, 19 mmol, 1.1 eq.) is added dropwise. The resulting mixture is stirred at −78° C. for 1 hr, and N-fluorobenzenesulfonimide (5.99 g, 19 mmol, 1.1 eq.) is added. The resulting solution is stirred at −78° C. for 2 hr, warmed to rt slowly, and then stirred at rt overnight. Water (50 ml) is added to quench the reaction, and THF is evaporated. The residue is extracted with EtOAc (75 ml×2) and the combined organic layers are washed with water and brine, dried and concentrated to give crude 1-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole as a yellow oil. LCMS 313 (M+1).

1. stirringThe resulting solution is stirred at −78° C
2. waitAfter 1 hr
3. stirringThe resulting mixture is stirred at −78° C. for 1 hr
4. stirringThe resulting solution is stirred at −78° C. for 2 hr
5. temperaturewarmed to rt slowly
6. stirringstirred at rt overnight
7. customto quench
8. customthe reaction, and THF
9. customis evaporated
10. extractionThe residue is extracted with EtOAc (75 ml×2)
11. washthe combined organic layers are washed with water and brine
12. customdried
13. concentrationconcentrated

ORD-Eintrag

ord-063302fd527f4632a4a26455de7386ac

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07728009B1