Tert-butyl 8-chloro-3-phenyl[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate → Tert-butyl 8-(5-methylpyridin-2-yl)-3-phenyl[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of tert-butyl 8-chloro-3-phenyl[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate (0.22 g, 0.67 mmol) and bis(tri-tert-butylphosphine)palladium(0) (17.1 mg, 33 μmol) in dioxane (2 mL) was added 5-methyl-2-pyridylzinc bromide (0.5 M in THF; 4.0 mL, 2.0 mmol). The mixture was heated 75° C. After 181, the mixture was cooled to ambient temperature and concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate) gave the title compound (69 mg): LC-MS [M+1]=387.1.

Provenance & Evidence