Dichloromethane → 6-((7-(4-chlorophenyl)-5-methyl-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

In a pressure tube, to a stirring solution of 6-((8-bromo-7-(4-chlorophenyl)-5-methyl-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-2(3H)-yl)methyl)nicotinonitrile (54 mg, 0.11 mmol) in THF (2 mL) at room temperature under argon was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (45 mg, 0.22 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (9 mg, 0.011 mmol) and powdered K3PO4 (60 mg, 0.28 mmol). The resulting suspension was stirred and heated at 100° C. under argon for 7 h. The reaction mixture was filtered through filter paper and the filtrate was concentrated under vacuum to a dark brown solid. The crude product thus obtained was purified by reverse phase preparative HPLC (without TFA) to obtain 31 mg of the title compound as a yellow solid. HPLC/MS: retention time=2.482 min, [M+H]+=453.

Provenance & Evidence