CEP 33779

747413-17-8

1257704-13-4

1257704-57-6

GENERAL STEPS: To an oven-dried reaction tube was added palladium acetate (10 mg), 2,2'-bis(dicyclohexylphosphino)biphenyl (30 mg), 8-[4-(methylsulfonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine (75 mg), 1-(3-bromophenyl)-4-methylpiperazine (80 mg), cesium carbonate (270 mg) and 1 ,4-dioxane (5 mL). The reaction tube was evacuated and backflushed three times with nitrogen and then sealed. The reaction mixture was heated at 80°C for 72 hours. After completion of the reaction, the mixture was cooled to room temperature. The cooled mixture was diluted with dichloromethane (10 mL), filtered through a diatomaceous earth plug and rinsed with dichloromethane. The filtrate was concentrated by evaporation and purified by column chromatography (using an ISCO automated purification system, an amine-modified silica gel column, and an eluent of 5% to 100% ethyl acetate in hexane solution). The target compound N-[3-(4-methyl-1-piperazinyl)phenyl]-8-[4-(methylsulfonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-amine (Compound A) was obtained as a yellow solid (70 mg). Melting point: 232-234 °C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.49 (d, J = 7.2 Hz, 1H), 8.25 (d, J = 7.5 Hz, 2H), 8.08 (d, J = 7.9 Hz, 2H), 7.65 (d, J = 7.7 Hz, 1H), 7.38 (s, 1H), 7.27- 7.20 (m, 1H), 7.04-6.95 (m, 2H), 6.84 (s, 1H), 6.60 (d, J = 8.0 Hz, 1H), 3.30-3.25 (m, 4H), 3.10 (s, 3H), 2.63-2.58 (m, 4H), 2.38 (s, 3H). MS: MS = 463 (MH)+.