1-Methylpiperazine → HCID 49838144, compound

Participants

Reaction Conditions

Reaction Steps

To an oven dried tube was added (8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-(4-methoxy-phenyl)-amine (50.0 mg, 0.157 mmol), 1-methyl-piperazine (21.0 L, 0.189), palladium acetate (7.0 mg, 0.031 mmol), dicyclohexyl-(2′,4′,6′-triisopropyl-biphenyl-2-yl)-phosphane (15.0 mg, 0.0315 mmol, X-Phos), potassium phosphate (83.0 mg, 0.391 mmol) and 1,4-dioxane (3 mL) and kept under an atmosphere of nitrogen. The tube was evacuated and backflushed with nitrogen three times. The tube was sealed and heated at 100° C. for 18 hours. The mixture was cooled to room temperature and diluted with dichloromethane (10 mL). The suspension was filtered and the filtrate was evaporated. The residue was purified via chromatography using amine modified silica gel column (4.7 g) and 5%→100% ethyl acetate:hexane solvent gradient. The title compound was isolated as a tan foam (0.025 g, 47%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.04 (dd, J=6.5, 1.0 Hz, 1H), 7.51-7.46 (m, 2H), 6.93-6.88 (m, 2H), 6.74 (dd, J=7.8, 1.0 Hz, 1H), 6.58 (s, 1H), 3.80 (s, 3H), 3.55-3.45 (m, 4H), 2.71-2.65 (m, 4H), 2.39 (s, 3H). MS=339 (MH)+.

Provenance & Evidence