Potassium Phosphate, Tribasic → (S)-2-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-fluoro-6-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 2-bromo-6-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-fluorobenzaldehyde 102b (100 mg, 0.24 mmol), (S)-1-methyl-3-(5-(2-methyl-4-(oxe-tan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 105f (115 mg, 0.24 mmol), PdCl2(dppf) (22 mg, 0.03 mmol), K3PO4 (102 mg, 0.48 mmol), sodium acetate (39 mg, 0.48 mmol), THF (15 mL), and water (5 mL). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 2 h. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 40:1 dichloromethane/methanol to afford 104a as a yellow solid (82 mg, 49%). MS: [M+H]+ 696.3

Provenance & Evidence