Sodium Carbonate → HCID 118092560, compound

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 (6.5 g, 17.1 mmol), 5-bromopyridine-2-carboxylic acid (3.92 g, 19.4 mmol), aqueous sodium carbonate (2M, 17.1 mL, 34.3 mmol) in dioxanes (57.1 mL) was flushed and purged with Ar(g) (3×). PdCl2(dppf)-dichloromethane adduct (646 mg, 0.791 mmol) was then added to the reaction mixture and heated at 130° C. for 10 hours. Upon cooling, the reaction mixture was filtered through a CELITE pad and washed with dioxane. The crude reaction mixture was concentrated under reduced pressure and diluted with 90% MeCN and 10% 2M HCl (aq). The crude solid was isolated by filtration and was recrystallized from dichloromethane to yield 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carboxylic acid as an off-white powder. MS APC calc'd for C18H14F3N4O2 [M+H]+ 375. found 375. 1H NMR (500 MHz, DMSO-d6) δ 10.32 (s, 1H), 8.95 (s, 1H), 8.84 (d, J=5.4, 1H), 8.18 (d, J=9.6, 1H), 8.12 (d, J=9.3, 1H), 8.05 (s, 1H), 7.28 (s, 2H), 2.38 (s, 3H).

Provenance & Evidence