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

Participants

Reaction Conditions

Reaction Steps

To mixture of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (12.0 g, 34.96 mmol) and PdCl2(dppf) (1.28 g, 1.75 mmol) is added a 0.5 M solution of 3-methyl-2-thienylzinc bromide in THF (100 mL, 50.0 mmol). The mixture is stirred at 65° C. overnight, diluted with EtOAc (500 mL), washed with 10% citric acid (500 mL), water (400 mL), brine (400 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (10%-20% EtOAc/hexane gradient) furnish the title compound (8.83 g, 28.17 mmol, 81%). 1H NMR (CDCl3), δ 0.92 (t, J=7.4 Hz, 6H), 1.78-1.95 (m, 4H), 2.18 (s, 3H), 2.50 (s, 3H), 2.54 (s, 3H), 3.33-3.43 (m, 1H), 6.69 (s, 1H), 7.06 (d, J=4.9 Hz, 1H), 7.46 (d, J=4.9 Hz, 1H). LC/MS (m/z): calcd. for C18H23N3S (M+H)+: 314.6; found: 314.2.

Provenance & Evidence