Potassium Carbonate → HCID 68746480, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of palladium (II) acetate (0.163 g, 0.72 mmol, 0.1 equiv.) and 1,1′-bis(di-tert-butylphosphino)ferrocene (0.344 g, 0.72 mmol, 0.1 equiv.) in acetonitrile (27 mL) was added (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 (3.35 g, 7.25 mmol, 1 equiv.) and 6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazole-2-yl)pyridine-3-ylboronic acid Intermediate 9 (2.64 g, 7.32 mmol, 1.01 equiv.) and a solution of potassium carbonate (1.5 g, 10.87 mmol, 1.5 equiv.) in water (9 mL). This was stirred at 80° C. for 2 h. The reaction was cooled to room temperature and diluted with water. The precipitate was washed with water and dried. The compound was purified via silica gel chromatography and concentrated to afford (S)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-7-fluoro-1-(1-hydroxy-3,3-dimethylbutan-2-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Intermediate 76 (1.2 g, 25%). Calcd for C29H30F4N6O5S [M+H]+: 651.2.

Provenance & Evidence