Methyl iodide → HCID 12150667, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4,6-dichloro-5-(3-isopropyl-4-methoxy-phenoxy)-1H-indole-2-carboxylic acid ethyl ester (50 mg, 0.12 mmol) in N,N-dimethylformamide (1 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 4.3 mg, 0.18 mmol) and the mixture was stirred at 0° C. for 30 minutes. To which at 0° C. was added iodomethane (15 μL, 0.24 mmol). The solution was warmed to room temperature, stirred for 19 hours, quenched with 1M hydrochloric acid (15 mL) and extracted with ethyl acetate (15 mL). The organic extract was washed with 1M hydrochloric acid (4 times 20 mL), brine (20 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative thin layer chromatography (50% CH2Cl2 in hexane) to afford the title compound (46 mg). 1H NMR (400 MHz, CDCl3) δ7.42 (s, 1H), 7.33 (s, 1H), 6.85 (d, 1H), 6.65 (d, 1H), 6.42-6.39 (dd, 1H), 4.05 (s, 3H), 3.91 (s, 3H), 3.91 (s, 3H), 3.74 (s, 3H), 3.27-3.23 (m, 1H), 1.15 (d, 6H).

Provenance & Evidence