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

Participants

Reaction Conditions

Reaction Steps

To a flask containing 5-bromo-2-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-thiophene-3-carbonitrile (0.25 g, 0.62 mmol) and PdCl2(dppf) (0.024 g, 0.033 mmol) is added a solution of 0.5 M 6-methyl-2-pyridylzinc bromide in THF (2.50 mL, 1.24 mmol). The solution is heated at 65° C. overnight, diluted with EtOAc (30 mL), washed with sat. NH4Cl (2×30 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (15%-25% EtOAc/hexane gradient), furnish the title compound (0.11 g, 0.26 mmol, 39%). 1H NMR (CDCl3) δ 0.87 (t, J=7.5 Hz, 6H), 1.76-1.92 (m, 4H), 2.57 (s, 3H), 2.58 (s, 3H), 2.65 (s, 3H), 3.26-3.35 (m, 1H), 6.75 (s, 1H), 7.09 (d, J=7.5 Hz, 1H), 7.49 (d, J=7.9 Hz, 1H), 7.63 (dd, J=7.9, 7.5 Hz, 1H), 7.74 (s, 1H). LC/MS (m/z): calcd. for C24H25N5S (M+H)+: 416.6; found: 416.2.

Provenance & Evidence