Methanol → HCID 58236944, compound

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Reaction Steps

To a mixture of ethyl {2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (500 mg), tetrahydrofuran (20 mL) and methanol (5 mL) was added lithium borohydride (110 mg) at 0° C. The whole was stirred at room temperature for 2 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2 to 9:1, volume ratio) to give a pale yellow amorphous solid. The solid was crystallized from ethyl acetate-diethyl ether to give the title compound (210 mg, 46%) as pale yellow crystals. The crystals were recrystallized from ethyl acetate-diethyl ether to give pale yellow prisms. MS 476 (MH+). mp 172-173° C.

Provenance & Evidence