Nitrogen → HCID 59234644, compound

Participants

Reaction Steps

3-Bromo-1-(4-chlorobutyl)-2(1H)-pyridinone (400 mg, 1.51 mmol and then 627 mg, 4.54 mmol) was added to a solution of (6-methyl-3-pyridinyl)boronic acid (commercial Synchem OHG product list) (311 mg, 2.27 mmol) in dioxane (5K2CO3 ml). The mixture was degassed bubbling with N2 for 10′ and then triphenylphosphine (120 mg, 0.45 mmol) and palladium(II)acetate (34 mg, 0.15 mmol) were added. The reaction mixture was stirred at reflux for 5 h and then at room temperature for 18 hours. Further (6-methyl-3-pyridinyl)boronic acid (Synchem OHG product list) (60 mg, 0.43 mmol), triphenylphosphine (78 mg, 0.3 mmol) and palladium(II)acetate (22 mg, 0.1 mmol) were added and the reaction was stirred for additional 4 hours at 80° C. The reaction was cooled and concentrated by removing the solvent under reduced pressure. Water was added to the crude and the organic layers were extracted with DCM. The organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with a gradient of methanol in DCM (from 0 to 5%) to afford the title compound (280 mg, 67%).

Provenance & Evidence