Methyl iodide → HCID 70664846, compound

Participants

Reaction Steps

To a solution of methyl 3-(cyclohexylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200 mg, 0.53 mmol) in tetrahydrofuran (30 mL) was added sodium hydride (105.5 mg, 4.40 mmol) and CH3I (299.9 mg, 2.11 mmol), and the reaction was allowed to proceed with stirring overnight at room temperature. The reaction was then quenched by the addition of water (50 mL), adjusted pH to 5 with HCl (3N). The resulting solution was extracted with ethyl acetate (3×80 mL) and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the crude product. The crude product was re-crystallized from ethyl acetate:petroleum ether (1:5) to afford 3-(cyclohexyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid (100 mg, 48%) as a light yellow solid.

Provenance & Evidence