Sodium Carbonate → Tert-butyl 4-(2-chloro-4-((1-(quinolin-2-YL)azetidin-3-YL)oxy)pyrimidin-5-YL)-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Steps

To a solution of 2-(3-((5-bromo-2-chloropyrimidin-4-yl)oxy)azetidin-1-yl)quinoline (see PREPARATION P2.11; 600 mg, 1.5 mmol) in 1,4-dioxane (15 mL) was treated with Na2CO3 (318 mg, 3 mmol) in 3 mL of water as a solution, followed by additional of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (556 mg 1.8 mmol) and Pd(dppf)Cl2 (110 mg, 0.15 mmol). The resulting mixture was heated at refluxing overnight under N2 atmosphere. The solution was filtered through CELITE®, and the filter was concentrated. The residue was purified by flash column chromatography on silica gel (20% to 70% EtOAc in petroleum ether) to give the title product (472 mg, 0.95 mmol, yield: 63%). ESI-MS (M+1): 494 calc. for C26H28ClN5O3 493.

Provenance & Evidence