Sodium Carbonate → HCID 46913527, compound

Participants

Reaction Conditions

Reaction Steps

N-(5-(7-bromoimidazo[1,2-a]pyridin-3-yl)-2-chloropyridin-3-yl)dimethylaminosulfonamide. To a 100 mL round bottom flask was added N-(5-bromo-2-chloropyridin-3-yl)dimethylaminosulfonamide (0.220 g, 0.699 mmol), Bis(pinacolato)diboron (0.266 g, 1.049 mmol), 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.051 g, 0.070 mmol), potassium acetate (0.069 g, 0.699 mmol) and dioxane (20 mL). The resulting mixture was heated at 95° C. under N2 for 4 h. The reaction mixture was removed from the hot plate followed by the addition of 7-bromo-3-iodoimidazo[1,2-a]pyridine (0.226 g, 0.699 mmol), sodium carbonate (0.874 mL, 1.748 mmol), and 1,1′-bis(diphenylphosphino)ferrocene]dichloride palladium(II) (0.051 g, 0.070 mmol). The resulting mixture was then reheated at 95° C. under N2 for 20 h. The reaction was cooled to rt. The solvent was removed. The residue was partitioned between pH 7-buffer (1M TRIS-HCL) and CHCl3. The organic layer was dried over MgSO4 and concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 40 g SiO2, DCM:EtOAc:MeOH (2M NH3)=80%:17%:3%, Flow=40 mL/min) to afford the desired product as brown foam-like solid (50.0 mg). MS (ESI pos. ion) m/z: 429.8. Calcd exact mass for C14H13BrClN5O2S: 428.9. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.91 (s, 6H) 6.88 (br. s., 1H) 7.04 (d, J=7.89 Hz, 1H) 7.78 (s, 1H) 7.93 (s, 1H) 8.08 (s, 1H) 8.16 (d, J=7.16 Hz, 1H) 8.34 (s, 1H).

Provenance & Evidence