Sodium Iodide → HCID 58365165, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-((4-methylpiperidin-4-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (74 mg, 0.16 mmol) in acetonitrile (1.7 mL) was added sodium iodide (26 mg, 0.17 mmol) and 1-bromo-2-methoxyethane (16 uL, 0.17 mmol). The reaction mixture was warmed to 50° C. for 18 hours. The mixture was allowed to cool and then 1-bromo-2-methoxyethane (65 uL, 0.69 mmol) and N,N-diisopropylethylamine (29 uL, 0.16 mmol) were added and the mixture was heated at 50° C. for an additional 4 hours. The cooled reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (10 mL), water (20 mL), and methylene chloride (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 1-20% methanol in dichloromethane) to afford the title compound as an oil, which was used in the next step without any further purification (36 mg, 43%).

Provenance & Evidence