Sodium Carbonate → HCID 68747842, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottomed flask ethyl 1-[(2S)-1-{[bis(benzyloxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-bromo-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Intermediate 28, 700 mg, 1.05 mmol), 6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid (Intermediate 9, 565 mg, 1.28 mmol) and aqueous sodium carbonate (125 mg, 1.18 mmol) were combined and suspended in dimethylformamide (10 mL). Argon gas was purged through the above suspension for 15 min. Tetrakis (triphenylphosphine) palladium (122 mg, 0.10 mmol) was added under argon atmosphere and the reaction mixture was heated to 80° C. for 3 h. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered through celite, the filtrate was poured into water to give a solid. The solid was filtered and washed with water then dried to afford 330 mg (50%) of ethyl 1-[(2S)-1-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate.

Provenance & Evidence