Imidazole → 3-Imidazol-1-yl-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline

Participants

Reaction Conditions

Reaction Steps

To a reaction vial was added 3-bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (71 mg, 0.2 mmol, 1.0 equiv), CuI (7 mg, 0.04 mmol, 0.008 equiv), L-proline (9 mg, 0.08 mmol, 0.4 equiv) and K2CO3 (83 mg, 0.60 mmol, 3.0 equiv). The system was evacuated and filled with nitrogen (3×). A solution of degassed imidazole (27 mg, 0.4 mmol, 2.0 equiv) in DMSO (1 mL) was then added. The reaction was heated at 120° C. for 18 hours. The solvent was removed in vacuo and the residue absorbed onto silica gel and purified by flash chromatography (SiO2, CH2Cl2:CH3OH 100:0-90:10 to return the title compound (15 mg, 22% yield). Analytical data presented in Table 2.

Provenance & Evidence