Potassium Carbonate → HCID 69621312, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5)-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(1-hydroxy-3,3-dimethylbutan-2-ylamino)acrylate Intermediate 80 (4.47 g, 9.27 mmol, 1 equiv.) in DMF (46 mL) was added potassium carbonate (1.92 g, 13.9 mmol, 1.5 equiv.) was added, and the reaction was stirred at 70° C. for 30 min. The reaction was cooled to 0° C. and quenched with saturated ammonium chloride (5 mL). The reaction was partitioned between water (50 mL) and dichloromethane (50 mL). The aqueous layer was extracted with dichloromethane (2×30 mL), and the organics were concentrated. The compound was purified via silica gel chromatography and concentrated to afford (S)-ethyl 7-fluoro-1-(1-hydroxy-3,3-dimethylbutan-2-yl)-6-iodo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate Intermediate 78 as a solid (3.37 g, 79%). Calcd for C17H26FIN2O4. H1NMR (d6-DMSO) δ 8.69 (s, 1H), 4.24 (m, 3H), 3.98 (m, 2H), 1.28 (t, 3H), 0.95 (s, 9H).

Provenance & Evidence