Nitrogen → HCID 77106758, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-Morpholin-4-yl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanone (129 mg, 0.39 mmol) and 5-bromo-3-(1-isopropyl-1H-[1,2,3]triazol-4-yl)-pyridin-2-ylamine (100 mg, 0.35 mmol) in 1,4-dioxane (6.0 mL)/water (4.0 mL) was added Cs2CO3 (284 mg, 0.87 mmol) at room temperature. N2 was purged through the reaction mixture for 10 min. Pd(PPh3)4 (20 mg, 0.017 mmol) was added and through the reaction mixture N2 was purged for 10 min and stirred at 100° C. for 16 h. The reaction mixture was cooled to RT, diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure. Crude compound was purified by column chromatography using 100-200 mesh silica gel and eluted with 2-3% MeOH in DCM to afford 40 mg (yield: 27.7%) of the title compound as brown semisolid. Product was converted to its HCl salt by using 2M HCl in ether to afford 42 mg of an off-white solid.

Provenance & Evidence