Potassium Phosphate, Tribasic → 3-(4-(aminomethyl)phenyl)-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine (57.6 mg, 0.21 mmol), (4-carbamoylphenyl)boronic acid (87.4 mg, 0.53 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (7.7 mg, 0.011 mmol) and potassium phosphate (134 mg, 0.63 mmol) was added 1:1 Dimethoxyethane/water (0.75 mL). The resulting mixture was heated at 160° C. (microwave) for 6 min. The reaction was then filtered and diluted with a mixture of 1:1:1 methanol/water/acetonitrile, and then filtered again. The filtration was finally purified by preparative HPLC (neutral) to afford 3-(4-(aminomethyl)phenyl)-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine (9 mg, 14% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.29 (d, J=8.6 Hz, 2H), 7.98 (d, J=8.6 Hz, 2H), 7.89 (s, 1H), 7.66 (d, J=9.6 Hz, 1H), 6.79 (d, J=9.9 Hz, 1H), 3.69 (t, J=5.6 Hz, 2H), 3.59 (t, J=5.4 Hz, 2H), 3.42 (s, 3H); LRMS (ESI) m/e 312.2 [(M+H)+, calcd for C16H18N5O2 312.2].

Provenance & Evidence