Potassium Carbonate → HCID 44540075, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of palladium (II) acetate (23.52 mg, 0.10 mmol, 0.1 equiv.) and 1,1′-bis(di-t-butylphosphino)ferrocene (49.7 mg, 0.10 mmol, 0.1 equiv.) in acetonitrile (3 mL) was added (S)-ethyl 1-(1-hydroxy-3-phenylpropan-2-yl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 51, 500 mg, 1.05 mmol), followed by 6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazole-2-yl)pyridine-3-ylboronic acid (Intermediate 17, 381 mg, 1.06 mmol) and a solution of potassium carbonate (217 mg, 1.57 mmol) in water (1 mL). The reaction mixture was stirred at 60° C. for 2 h, cooled to room temperature, and diluted with water (2 mL). The reaction mixture was partitioned between water (10 mL) and ethyl acetate (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL), and the organics were dried over sodium sulfate and concentrated to provide (S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-3-phenylpropan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate as a grey solid (619 mg, 89%).

Provenance & Evidence