3-(4,5-Dibromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine → 3-(4-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Participants

Reaction Steps

To a −78° C. solution of 3-(4,5-dibromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.22 g, 0.47 mmol) and THF (3 mL) is added 1.6 M n-BuLi (0.31 mL, 0.49 mmol). After 20 minutes the solution is quenched with water (1 mL), warmed to ambient temperature, diluted with EtOAc (30 mL), washed with brine (30 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (5%-10% EtOAc gradient) furnish the title compound (0.056 g, 0.14 mmol, 31%). 1H NMR (CDCl3) δ 0.87 (t, J=7.5 Hz, 6H), 1.73-1.93 (m, 4H), 2.09 (s, 3H), 2.44 (s, 3H), 2.49 (s, 3H), 3.27-3.36 (m, 1H), 6.68 (s, 1H), 7.44 (s, 1H). LC/MS (m/z): calcd. for C18H22BrN3S (M+H)+: 392.2; found: 392.3.

Provenance & Evidence