Benzeneethanamine, alpha-methyl-, phosphate (1:1) → 1-(4-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

N-(4-(3-bromopyridin-2-yloxy)phenyl)pyridin-2-amine hydrochloride (0.388 g, 1.14 mmol), 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (0.30 g, 1.2 mmol), potassium acetate (0.60 g, 10.2 mmol), and Amphos (0.063 g, 0.090 mmol) were taken up in 12 mL of 3:1 mixture of acetonitrile and water. The mixture was purged with nitrogen and heated to 90° C. for 15 h. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organics was washed with 30 mL of brine and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (10 to 100% EtOAc/hexane, then 5% MeOH in EtOAc) afforded 1-(4-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone as tan solid. MS (ESI, pos. ion) m/z: 387.0 (M+1). IC50 (uM) 0.002698.

Provenance & Evidence