Sodium Carbonate → HCID 118092639, compound

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled through a mixture of 2-[(5-bromopyridin-2-yl)amino]-2-methylbutanenitrile (327 mg, 1.29 mmol), N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (488 mg, 1.29 mmol), and sodium carbonate (2 M, 1.28 mL, 2.57 mmol) in 2-methyl-THF (6.43 mL) for ˜5 minutes. PdCl2(dppf)-dichloromethane adduct (52.5 mg, 0.064 mmol) was added and the reaction was heated to 100° C. overnight. The cooled reaction mixture was diluted with water and extracted dichloromethane (3×). The organic layer was concentrated under reduced pressure and purified by reverse phase chromatography to yield 2-methyl-2-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]amino}butanenitrile. MS APCI calc'd for C22H22F3N6 [M+H]+ 427. found 427. 1H NMR (500 MHz, CDCl3) δ 8.66 (d, J=5.3, 1H), 8.44 (s, 1H), 7.85-7.68 (m, 1H), 7.31 (t, J=17.9, 2H), 7.14-6.93 (m, 2H), 6.76 (d, J=9.3, 1H), 2.41 (s, 3H), 2.17-2.03 (m, 2H), 1.62 (s, 3H), 0.93 (t, J=7.3, 3H).

Provenance & Evidence