Ammonium Chloride → (2-{7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3-thiazol-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3-thiazole-5-carboxylate (242 mg) in tetrahydrofuran (25 mL) was added lithium aluminum hydride (50 mg) at 0° C. After the mixture was stirred at 0° C. for 30 min, ethanol was added dropwise until hydrogen did not generate. A saturated aqueous ammonium chloride solution was added to the mixture and the resulting yellow suspension was filtered through celite. The filtrate was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio) to give yellow crystals. The crystals were recrystallized from ethanol-ethyl acetate to give yellow crystals. The crystals were purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 90/10, volume ratio) to give yellow crystals. The crystals were recrystallized from ethanol-hexane to give the title compound (52 mg, 23%) as yellow crystals. MS 507 (MH+). mp 125-126° C.

Provenance & Evidence