Sodium Carbonate → Ethyl 3-hydroxy-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]cyclopentanecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (211 mg, 0.557 mmol), ethyl 3-(5-bromopyridin-3-yl)-3-hydroxycyclopentanecarboxylate (175 mg, 0.557 mmol), and sodium carbonate (2 M, 557 μl, 1.11 mmol) in 2-methyl THF (2785 μl) was purged with argon for 10 minutes. PdCl2(dppf)-CH2Cl2 adduct (22.7 mg, 0.028 mmol) was added to the reaction mixture and heated to 85° C. overnight. Upon cooling, the reaction was diluted with water and extracted with DCM (3×). The combined organic layers were dried under reduced pressure and purified by silica gel chromatography (ethyl acetate/hexanes) to afford ethyl 3-hydroxy-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]cyclopentanecarboxylate. MS ESI calc'd for C25H26F3N4O3 [M+H]+ 487. found 487.

Provenance & Evidence