Potassium Carbonate → HCID 87918846, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5)-ethyl 6-bromo-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydro-1,7-naphthyridine-3-carboxylate Intermediate 94 (511.5 mg, 1.2 mmol, 1 equiv.) in acetonitrile (3 mL) and DMF (1 mL) was added iodopropane (0.234 mL, 2.4 mmol, 2 equiv.) followed by potassium carbonate (663 mg, 4.8 mmol, 4 equiv.). The reaction was stirred at 60° C. for 2 days. The reaction was cooled to 23° C. and concentrated. The residue was re-suspended and partitioned between ethyl acetate (10 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL), and the organics were dried and concentrated to afford (S)-ethyl 6-bromo-4-oxo-1-((1-propylpyrrolidin-3-yl)methyl)-1,4-dihydro-1,7-naphthyridine-3-carboxylate (211 mg, 38%). Calcd for C19H24BrN3O3 [M+H]+: 424.0.

Provenance & Evidence