Methyl iodide → HCID 70665114, compound

Participants

Reaction Steps

To a solution of methyl 3-(o-toluidino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (145 mg, 0.37 mmol) in tetrahydrofuran (30 mL) was added sodium hydride (74.9 mg, 3.12 mmol) at 0° C. with stirring for 30 min, followed by the addition of CH3I (1.5 mL) dropwise. The reaction mixture was stirred overnight at room temperature. The reaction was then quenched with water (50 mL), adjusted to pH 5 with HCl (3N), and extracted with ethyl acetate (3×80 mL). The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the residue, which was purified by Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, water with 0.05% TFA and CH3CN (25% CH3CN up to 67% in 10 min); Detector, UV 220 nm] to afford 2-(4-fluorophenyl)-3-(methyl(o-tolyl)amino)quinoxaline-6-carboxylic acid as a light yellow solid (46.5 mg, 30%).

Provenance & Evidence