1-Butanol → HCID 86696411, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-allyl-3-bromoimidazo[1,2-b]pyridazin-6-amine (365 mg, 1.44 mmol), (4-(allylcarbamoyl)phenyl)boronic acid (615 mg, 3.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (62 mg, 0.085 mmol) was added n-butanol (3 mL) and 2 M aqueous sodium carbonate (2 mL). The resulting mixture was heated at 100° C. for 5 h. The reaction was then diluted with water, extracted with ethyl acetate, and purified by silica gel column (10% methanol in ethyl acetate) followed by preparative HPLC (acetonitrile/aqueous ammonium formate, Sunfire column) to afford N-allyl-4-(6-(allylamino)imidazo[1,2-b]pyridazin-3-yl)benzamide as a white solid: 1H NMR (METHANOL-d4) δ: 8.30-8.33 (d, J=8.4 Hz, 2H), 7.94 (d, J=8.4 Hz, 2H), 7.67 (d, J=9.6 Hz, 1H), 6.78 (d, J=9.6 Hz, 1H), 5.9-6.2 (m, 2H), 5.1-5.4 (m, 4H), 4.00 (m, 4H); LRMS (ESI) m/z 334.2 [(M+H)+, calcd for C19H19N5O 333.4]

Provenance & Evidence