Potassium Phosphate, Tribasic → 4-Fluoro-2-(1-methyl-5-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-6-(1-oxo-6,7,8,9-tetrahydropyridazino[4,5-b]indolizin-2(1H)-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 127f (125.0 mg, 0.32 mmol), 1-methyl-3-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-5-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 113f (155.0 mg, 0.32 mmol), sodium acetate (53.0 mg, 0.64 mmol), K3PO4 (135.7.0 mg, 0.64 mmol), PdCl2(dppf) (50.0 mg, 0.06 mmol), acetonitrile (25 mL), and water (1 mL). The system was subjected to 3 cycles of vacuum/argon flush and heated at 100° C. for 3 hours. It was then evaporated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 30:1 methylene chloride/methanol to afforded 127g compound (108 mg, 51%) as a brown solid. MS: [M+H]+ 665.4.

Provenance & Evidence