Methanol → HCID 67118480, compound

Participants

Reaction Steps

To an ice-cooled and stirred solution of ethyl {2-[6-fluoro-7-(2-methoxyethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (200 mg) in tetrahydrofuran (8 mL)-methanol (6 mL) was added lithium borohydride (40 mg), and the mixture was stirred at room temperature for 2.5 h, followed by an addition of lithium borohydride (40 mg). After the mixture was stirred at room temperature for 2 h, lithium borohydride (40 mg) was further added thereto. After stirring at room temperature for 2 h, the reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography (ethyl acetate:hexane=60:40 to 100:0, volume ratio) to give colorless crystals, which were recrystallized from tetrahydrofuran-ethyl acetate-hexane to give the title compound (76 mg, 41%) as colorless crystals. MS 510 (MH+). mp 160-161° C.

Provenance & Evidence