Sodium Carbonate → N-(2-Chloro-5-(6-(pyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)pyridin-3-yl)dimethylaminosulfonamide

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Reaction Conditions

Reaction Steps

N-(5-(6-bromoimidazo[1,2-a]pyridin-3-yl)-2-chloropyridin-3-yl)dimethylaminosulfonamide. To a 5 mL microwave tube was added N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)dimethylaminosulfonamide (0.200 g, 0.553 mmol), 6-bromo-3-iodoimidazo[1,2-a]pyridine (0.214 g, 0.664 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.020 g, 0.028 mmol), sodium carbonate (0.691 mL, 1.383 mmol), and dioxane (3 mL). The resulting mixture was sealed and underwent microwave heating at 110° C. for 15 min. The solvent was removed. The residue was partitioned between pH 7 buffer (1M TRIS-HCL) and DCM. The aqueous layer was extracted more with DCM (2×10 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 12 g SiO2, hexanes:acetone=80%:20%, Flow=30 mL/min). The solvent was removed in vacuo to afford the desired product as brown solid (180 mg). MS (ESI pos. ion) m/z: 429.7. Calcd exact mass for C14H13BrClN5O2S: 428.9. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.94 (s, 6H) 7.36 (d, J=9.65 Hz, 1H) 7.63 (d, J=9.50 Hz, 1H) 7.79 (s, 1H) 8.09 (s, 1H) 8.34 (s, 1H) 8.42 (s, 1H).

Provenance & Evidence