1,2-Dimethoxyethane → 5-(6-Butylamino-imidazo[1,2-b]pyridazin-3-yl)-indan-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (400 mg, 1.5 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (770 mg, 3.0 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (240 mg, 0.30 mmol), potassium phosphate (1.0 g, 4.5 mmol), DME (6 mL) and H2O (2 mL) was heated in a sealed vessel at 80° C. for 12 h. The reaction was cooled to RT, then the organic layer was separated and concentrated under reduced pressure to afford an oil that was purified by flash chromatography (SiO2) to afford 5-(6-butylamino-imidazo[1,2-b]pyridazin-3-yl)-indan-1-one (410 mg, 85%) as a pink solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.52 (s, 1H), 8.22 (d, J=8.1 Hz, 1H), 8.07 (s, 1H), 7.78 (s, 1H), 7.65 (d, J=8.1 Hz, 1H), 7.17 (t, J=5.4 Hz, 1H), 6.75 (d, J=9.6 Hz, 1H), 3.22-3.42 (m, 3H), 3.05-3.18 (m, 2H), 2.58-2.71 (m, 2H), 1.58-1.73 (m, 2H), 1.34-1.51 (m, 2H), 0.89-1.00 (m, 3H); LCMS (ESI) m/e 321.2 [(M+H)+, calcd for C19H21N4O 321.2].

Provenance & Evidence