Iodobenzene → HCID 59276430, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine. To a solution of 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (2 g, 9.39 mmol) in 100 mL of dioxane was added iodobenzene (3.83 g, 18.78 mmol), sodium tert-butoxide (1.804 g, 18.78 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (1.086 g, 1.878 mmol) and tris(dibezylideneacetone)palladium (0.903 g, 0.986 mmol) at room temperature under nitrogen. The reaction mixture was heated at 100° C. for 2 h. Upon completion of the reaction, as indicated by LCMS, the reaction mixture was poured into water/brine, and extracted with ethyl acetate several times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by silica gel column chromatography (eluting with 0-80% ethyl acetate in hexanes) to give the title compound as a brown solid (1.3 g, 48% yield). 1H NMR (400 MHz DMSO-d6) δ (ppm) 9.84 (s, 1H), 7.74-7.71 (m, 2H), 7.62-7.60 (m, 1H), 7.52-7.48 (m, 1H), 7.40-7.38 (m, 1H), 7.32-7.28 (m, 2H), 6.92-6.88 (m, 1H); MS (ESI) m/z 290.13 [M+1]+

Provenance & Evidence