Tetrahydrofuran → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-5-pyridin-2-yl-thiophen-2-yl)-imidazo[1,2-b]pyridazine

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Reaction Conditions

Reaction Steps

To a mixture of 3-(5-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.50 g, 1.27 mmol) and PdCl2(dppf) (0.047 g, 0.064 mmol) is added a 0.5 M solution of 2-pyridylzinc bromide in THF (5.1 mL, 2.55 mmol). The mixture is stirred at 65° C. overnight, diluted with EtOAc (50 mL), washed with 10% citric acid (50 mL), water (40 mL), brine (40 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (20%-40% EtOAc/hexane gradient) furnish the title compound (0.45 g, 1.15 mmol, 89%). 1H NMR (CDCl3), δ 0.88 (t, J=7.5 Hz, 6H), 1.75-1.93 (m, 4H), 2.17 (s, 3H), 2.52 (s, 6H), 3.30-3.39 (m, 1H), 6.67 (s, 1H), 7.12-7.16 (m, 1H), 7.53 (s, 1H), 7.63-7.71 (m, 2H), 8.57 (dt, J=1.3, 4.8 Hz, 1H). LC/MS (m/z): calcd. for C23H26N4S (M+H)+: 391.6; found: 391.2.

Provenance & Evidence