Potassium Phosphate, Tribasic → 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (100 mg, 0.37 mmol), (4-(methylcarbamoyl)phenyl)boronic acid (166 mg, 0.93 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (15 mg, 0.02 mmol) and potassium phosphate (236 mg, 1.11 mmol) was added 1:1 Dimethoxyethane/water (5 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 (acidic) to afford 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)-N-methylbenzamide (32.1 mg, 27% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.21-8.41 (m, 2H), 7.86-7.94 (m, 3H), 7.64 (d, J=9.6 Hz, 1H), 6.74 (d, J=9.6 Hz, 1H), 3.35-3.44 (m, 5H), 2.97 (s, 3H), 1.68-1.77 (m, 2H), 1.46-1.56 (m, 2H), 1.03 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 324.4 [(M+H)+, calcd for C18H22N5O 324.2].

Provenance & Evidence