Acetonitrile → 3-(6-tert-Butyl-8-fluoro-1-oxo-1,2-dihydrophthalazin-2-yl)-5-[1-methyl-5-({5-[(2S)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-6-oxo-1,6-dihydro-pyridin-3-yl]pyridine-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A 25 mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 109a (118 mg, 0.29 mmol), 1-methyl-3-({5-[(2S)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-one 105f (140 mg, 0.29 mmol), Pd(dppf)Cl2 (24.8 mg, 0.03 mmol), KOAc (58.9 mg, 0.60 mmol), K3PO4.3H2O (159.8 mg, 0.60 mmol), acetonitrile (6 mL) and water (3 d). After three cycles of vacuum/argon flush, the mixture was heated at 110° C. for 2 h. The reaction mixture was then cooled to room temperature, filtered and the filtrate was evaporated in vacuo. The residue was purified by prep-TLC developing with dichloromethane/methanol (20:1, UV) to afford 109b (95 mg, 36%) as a red solid. MS: [M+H]+ 679

Provenance & Evidence