Sodium Carbonate → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-4-pyridin-3-yl-thiophen-2-yl)-imidazo[1,2-b]pyridazine

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A solution of 3-(4-bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.25 g, 0.64 mmol), pyridine-3-boronic acid (0.086 g, 0.70 mmol), 2 M Na2CO3 (0.48 mL, 0.96 mmol) and, n-PrOH (3 mL), is degassed with nitrogen for 10 minutes. Pd(OAc)2 (2.7 mg, 0.0013 mmol) and PPh3 (0.010 g, 0.038 mmol) are added and the solution is heated at 90° C. overnight. The solution is diluted with EtOAc (30 mL), washed with 10% Na2CO3 (30 mL), water (30 mL), brine (30 mL), dried over MgSO4, filtered, and concentrated. The residue is purified by ISCO (20-40% EtOAc gradient) furnish the title compound (0.051 g, 0.13 mmol, 20%). 1H NMR (CDCl3) δ 0.88 (t, J=7.5 Hz, 6H), 1.74-1.92 (m, 4H), 2.09 (s, 3H), 2.50 (s, 3H), 2.52 (s, 3H), 3.29-3.40 (m, 1H), 6.69 (s, 1H), 7.33-7.43 (m, 1H), 7.47 (s, 1H), 7.80 (d, J=7.9 Hz, 1H), 8.61 (bs, 1H), 8.78 (bs, 1H). LC/MS (m/z): calcd. for C23H26N4S (M+H)+: 391.2; found: 391.4.

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