5-Morpholinopyridin-2-amine → 6-chloro-N-(5-morpholinopyridin-2-yl)imidazo[1,2-a]pyridin-8-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromo-6-chloroimidazo[1,2-a]pyridine, HCl (600mg, 2.24 mmol), 5-morpholinopyridin-2-amine (482 mg, 2.69 mmol), BINAP (279 mg, 0.45 mmol), cesium carbonate (1824 mg, 5.60 mmol) in Toluene (12 mL) was sparged with nitrogen while stirring for 10 minutes. palladium(II) acetate (87 mg, 0.39 mmol) was then added and the reaction stirred at 105 °C for overnight. At ths stage LC/MS indicated that formation of the product. After this time, the reaction was cooled to room temperature, diluted with mixture of 1:1 methanol/DCM ( 100 mL) and filtered through celite. The filtrated concentrated under reduced pressure and the resulting residue purified by flash chromatography (silicagel, 0-10% DCM/Methanol, 25 minutes) to afford 6-chloro-N-(5-morpholinopyridin-2-yl)imidazo[1,2-a]pyridin-8-amine (482 mg, 65.3 %) as a solid. LC/MS (2 minute, Acid _CV10.olp method 330 (M + 1), 0.66 minutes. 1H NMR (400 MHz, DMSO- _d_ 6) d ppm 9.16 (s, 1 H) 8.30 - 8.34 (m, 1 H) 8.25 - 8.29 (m, 1 H) 7.98 - 8.03 (m, 1 H) 7.88 - 7.92 (m, 1 H) 7.54 - 7.57(m, 1 H) 7.36 - 7.47 (m, 2 H) 3.72 - 3.79 (m, 4 H) 3.05 - 3.12 (m, 4 H)

Provenance & Evidence