Hydrochloric Acid → HCID 67118722, compound

Participants

Reaction Steps

To a solution of ethyl (2-{7-(1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (490 mg) in tetrahydrofuran (10 mL) was added 1M methylmagnesium bromide tetrahydrofuran solution (7.6 mL) at 0° C. After the mixture was stirred at room temperature for 1.5 h, 1M methylmagnesium bromide tetrahydrofuran solution (3.4 mL) was added to the mixture again at room temperature. The mixture was stirred at room temperature for 2 h. Furthermore, 1M methylmagnesium bromide tetrahydrofuran solution (3.4 mL) was added to the mixture at room temperature and the mixture was stirred at room temperature for 30 min. The mixture was acidified with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=3/97 to 60/40, volume ratio) to give a yellow oil. The oil was crystallized from ethyl acetate-diethyl ether-hexane to give pale yellow crystals. The crystals were recrystallized from ethyl acetate-diisopropyl ether to give the title compound (50 mg, 10%) as pale yellow crystals. MS 503 (MH+).

Provenance & Evidence