Trifluoroacetic acid → N-(6-chloro-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A sealable vial was charged with N-(6-chloro-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (74.0 mg, 220 μmol), 4-pyridylboronic acid (32.4 mg, 264 μmol), sodium carbonate (93.2 mg, 880 μmol), and dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) (122 mg, 220 μmol). The vial was sealed with a septum cap and 1,4-dioxane (2 mL) was added under positive N2 flow followed by water (1 mL). The mixture was sparged with N2 for 10 min and heated at 80° C. for 18 h. The solution was concentrated and the residue was taken up in minimal MeOH/DMSO and purified by preparative HPLC (Gilson GX-281, Middletown, Wis.: 5-90% (0.1% TFA in CH3CN) in H2O over 15 min, Phenomenex, Zorbax 00F-4435-UO 150×30 mm, 5 micron) to afford N-(6-chloro-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (47.0 mg, 74.3% yield) as a trifluoroacetic acid salt. LCMS (ESI positive ionization) m/z: 288.3 (M+1).

Provenance & Evidence