Cesium carbonate → 3-Fluoro-7-methoxy-4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)quinoline

Participants

Reaction Steps

A sealable tube was charged with Pd2 dba3 (0.20 g, 0.22 mmol), racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (0.18 g, 0.44 mmol), (6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanol (0.100 g, 0.44 mmol), 4-chloro-3-fluoro-7-methoxyquinoline (0.14 g, 0.66 mmol), cesium carbonate (0.29 g, 0.88 mmol), and toluene and sealed. The mixture was heated at 100 C for 12 h. The mixture was allowed to cool to rt and the solid filtered, and rinsed with toluene. The solid was stirred with a mixture of EA, MeOH, CH2Cl2 and filtered. The filtrate was purified via flash chromatography using a MeOH in CH2Cl2 gradient. The resulting solid was triturated with CH2Cl2/Hexanes then purified by prep hplc. The title compound was collected as a white solid. M/Z=402.1 [M+H], calc 401.3994 for C22H16FN5O2.

Provenance & Evidence