Cesium carbonate → N-(4-(4-methylpiperazin-1-yl)phenyl)-5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(4-chlorophenyl)-5-(4-(morpholinomethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (300 mg, 0.7 mmol), 1-methylpiperazine (356 mg, 3.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (65 mg, 0.07 mmol), cesium carbonate (456 mg, 1.4 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (410 mg, 0.07 mmol) in 1,4-dioxane (2 mL) was irradiated by microwave heating to 160° C. for 20 min. The reaction mixture was diluted with EtOAc (300 mL), and filtered though celite. The filtrate was concentrated to give a black residue, which was purified by preparative thin layer chromatography (10% methanol in dichloromethane) to afford product (38.9 mg 11% yield). 1H NMR (400 MHz, CDCl3), δ: 7.96 (d, J=8 Hz, 2H), 7.52-7.42 (m, 6H), 6.92-6.87 (m, 3H), 6.68 (m, 1H), 3.79-3.72 (m, 4H), 3.59 (s, 2H), 3.18-3.12 (m, 4H), 2.6-2.55 (m 4H), 2.55-2.48 (m, 4H), 2.33 (s, 3H). LCMS (ESI) m/z: 484.1.

Provenance & Evidence