Reaktion #80646
ord-95775d212b1a4e538d645c2f826c107f
Reaktionsgleichung
Edukte
Reagenzien
Reaktionsbedingungen
Aufarbeitung
- 1workup.STIRRINGthe reaction mixture was stirred at -78° C. for 1 hour
- 2Temperaturthe reaction mixture was warmed to room temperature
- 3workup.STIRRINGwas stirred overnight
- 4SonstigeThe reaction was quenched with 50 mL of 1N HCl
- 5Extraktionthe aqueous phase was extracted with ethyl acetate (3×60 mL)
- 6WaschenThe combined organic layers were washed with brine
- 7Trocknendried over MgSO4
- 8Filtrationfiltered
- 9Einengenconcentrated
- 10SonstigeThe crude mixture was purified by chromatography on silica gel (ethyl acetate/hexane, 65:35)
Vorschrift
To a solution of diisopropylamine (0.7 mL, 0.005 mol) in 9 mL of dry THF was added butyllithium (BuLi) (2.83 mL of 1.62M solution in hexane, 4.6 mmol) at 0° C. The solution was stirred at this temperature for 5 minutes and cooled to -78° C. with a dry ice/isopropanol bath. A solution of 2-methyl-3-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (Example 46) (1.46 g, 3.8 mmol) in 12 mL of dry THF was added over 10 minutes and the reaction mixture was stirred at -78° C. for 1 hour. (Iodomethyl)trimethylsilane (1.23 g, 57 mmol) was added dropwise and the reaction mixture was warmed to room temperature and was stirred overnight. The reaction was quenched with 50 mL of 1N HCl and the aqueous phase was extracted with ethyl acetate (3×60 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by chromatography on silica gel (ethyl acetate/hexane, 65:35) to give 1.30 g of 2-methyl-3-[1-[4-[[2-(trimethylsilyl) ethyl]sulfonyl]phenyl]-4-(trifluoromethyl) -1H-imidazol-2-yl]pyridine as a white solid (74%): mp(DSC) 155°-157° C. Anal. Calc'd. for C21H24F3N3O2SSi: C, 53.94; H, 5.17; N, 8.99; S, 6.86. Found: C, 53.77; H, 4.94; N, 8.75; 6.98.