Potassium Carbonate → HCID 59415994, compound

Participants

Reaction Conditions

Reaction Steps

Palladium (II) acetate (0.027 g, 0.12 mmol) and 1,1′-bis(di-t-butylphosphino)ferrocene (0.058 g, 0.12 mmol) were dissolved in 1 ml of acetonitrile. Ethyl 1-(cis-2-hydroxycyclohexyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 121, 0.539 g, 1.22 mmol) and 6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-ylboronic acid (Intermediate 17, 0.444 g, 1.23 mmol) were added along with an additional 2 ml of acetonitrile. Potassium carbonate (0.253 g, 1.83 mmol) was dissolved in water (1.333 mL) then added to the mixture. The reaction was stirred at 100° C. for 30 min, then cooled to room temperature and quenched with water (2 ml). The precipitate was filtered off and washed with water, ethyl acetate and hexanes, then dried in a vacuum oven at 50° C. for 18 h to give 0.606 g (78%) of ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(cis-2-hydroxycyclohexyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate as a light brown solid.

Provenance & Evidence