Potassium Phosphate, Tribasic → 3-(6-aminopyridin-3-yl)-N-butylimidazo[1,2-b]pyridazin-6-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (75 mg, 0.28 mmol), tert-butyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate (107 mg, 0.33 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (10 mg, 0.014 mmol) and potassium phosphate (58 mg, 0.42 mmol) was added 3:1 acetonitrile/water (2 mL). The resulting mixture was heated at 145° C. (microwave) for 1000 s. The reaction was then filtered and concentrated. The residue was finally purified by preparative HPLC (neutral) to afford 3-(6-aminopyridin-3-yl)-N-butylimidazo[1,2-b]pyridazin-6-amine (50.3 mg, 47% yield) as a yellow solid: 1H NMR (METHANOL-d4) δ: 8.72 (d, J=1.8 Hz, 1H), 8.08 (dd, J=8.7, 2.3 Hz, 1H), 7.58 (s, 1H), 7.52 (d, J=9.7 Hz, 1H), 6.58-6.66 (m, 2H), 4.78-4.88 (m, 11H), 3.27-3.33 (m, 3H), 1.62 (d, J=7.1 Hz, 2H), 1.42 (d, J=7.9 Hz, 2H), 0.91-0.97 (m, 3H); LRMS (ESI) m/e 283.4 [(M+H)+, calcd for C15H19N6 283.2].

Provenance & Evidence