Methyl iodide → HCID 45254979, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of compound 48 (6.6 g, 12 mmol) in N,N-dimethylformamide (200 mL) was cooled to 0° C. Sodium hydride (1.0 g, 25 mmol) was added, resulting in bright orange slush. The reaction mixture was stirred for 1 hr at 0° C. before adding methyl iodide (890 mL, 14 mmol). After 3 hours, the reaction was quenched with methanol (100 mL) and the solids were collected by filtration to afford benzyl 4-(3-methyl-2-oxo-8-quinolin-3-yl-2,3-dihydro-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)piperidine-1-carboxylate (compound 49) (5.0 g, 73%).

Provenance & Evidence