Acetonitrile → butyl-[3-(1H-indazol-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine

Participants

Reaction Steps

A mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (140 mg, 0.50 mmol), (1H-indazole-5-boronic acid pinacol ester (150 mg, 0.60 mmol), dichloro-bis(triphenylphosphino) palladium (II) (20 mg, 0.025 mmol), potassium carbonate (110 mg, 0.75 mmol), acetonitrile (1.5 mL) and H2O (0.5 mL) was heated in a sealed conical vessel at 160° C. for 1000 s by microwave irradiation. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2 mL). The combined organic layers were concentrated under reduced pressure to afford an oil that was purified by reverse phase HPLC to afford butyl-[3-(1H-indazol-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine (100 mg, 65%) as a white solid: 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.62-8.68 (m, 1H), 8.13-8.20 (m, 2H), 8.02 (dd, J=8.8, 1.5 Hz, 1H), 7.94 (d, J=9.9 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.21 (d, J=9.9 Hz, 1H), 3.43 (t, J=7.2 Hz, 2H), 1.66-1.79 (m, 2H), 1.49 (dq, J=15.1, 7.4 Hz, 2H), 0.99 (t, J=7.5 Hz, 3H); LCMS (ESI) m/e 307.2 [(M+H)+, calcd for C17H19N6 307.2].

Provenance & Evidence