Sodium Carbonate → (R)-N-{dicyclopropyl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]methyl}-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (300 mg, 0.791 mmol), PdCl2(dppf)-dichloromethane adduct (32.3 mg, 0.040 mmol), and sodium carbonate (2 M, 0.791 mL, 1.58 mmol) were added to a solution of (R)—N-[(5-bromopyridin-2-yl)(dicyclopropyl)methyl]-2-methylpropane-2-sulfinamide (344 mg, 0.926 mmol) in 2-methyl-THF (2.60 mL) and flushed and purged with Ar(g). The reaction mixture was irradiated in a microwave reactor for 5 minutes at 170° C. Upon cooling, the reaction mixture was diluting with saturated aqueous NaHCO3 (10.0 mL) and extracted with ethyl acetate (20.0 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated under reduced pressure. The residue was purified by silica gel chromatography (0.5-3% methanol in dichloromethane) to yield (R)—N-{dicyclopropyl[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]methyl}-2-methylpropane-2-sulfinamide. MS APCI calc'd for C28H33F3N5OS [M+H]+ 544. found 544.

Provenance & Evidence