6-Amino-3-chloropyridazine → 3-Amino-4-bromo-6-chloropyridazine

Participants

Reaction Steps

To a solution of 6-chloropyridazin-3-amine (1.0 equiv) in MeOH (1M) at room temperature was added sodium bicarbonate (2.0 equiv.) and the resulting suspension was stirred at room temperature for 30 min before the dropwise addition of bromine (1.0 equiv.). The reaction mixture was stirred for 20 h. Upon concentration under vacuo, the crude residue was purified via silica gel column chromatography eluting with 100% heptanes to 80% ethyl acetate:heptanes to yield 4-bromo-6-chloropyridazin-3-amine in 50% yield. LCMS (m/z) (M+H)=207.8/209.8, Rt=0.47 min. 1H NMR (400 MHz, <cdcl3>) δ ppm 5.31-5.63 (m, 2H) 7.46-7.61 (m, 1H).

Provenance & Evidence