Sodium borohydride → HCID 12150687, compound

Participants

Reaction Steps

To a solution of 5-[3-(4-Fluoro-benzoyl)-4-hydroxy-phenoxy]-4,6-dimethyl-1H-indole-2-carboxylic acid ethyl ester (20 mg, 0.045 mmol) in ethanol (1 mL) at room temperature was added sodium borohydride (3.4 mg, 0.089 mmol), and the resulting solution was stirred at room temperature for 1 hour. The reaction was quenched with 1M HCl.(10 mL), diluted with ethyl acetate (10 mL). The ethyl acetate layer was separated, washed with 1M HCl (2 times 10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative thin layer chromatography (4% methanol in methylene chloride) to afford the title compound (17.5 mg) as a solid. 1H NMR (400 MHz, CDCl3) δ8.76 (s, 1H), 7.31-7.23 (m, 2H), 7.17 (s, 1H), 7.05 (s, 1H), 6.98 (t, 2H), 6.72 (d, 1H), 6.50 (dd, 1H), 6.36 (d, 1H), 5.84 (s, 1H), 4.40-4.34 (q, 2H), 2.25 (s, 3H), 2.14 (s, 3H), 1.38 (t, 3H). MS (APCI−) Calc:449.2, Found: 448.3 (M−1).

Provenance & Evidence