1-Methylimidazole → 8-(1-ethyl-propyl)-2,6-dimethyl-3-[3-methyl-5-(1-methyl-1H-imidazol-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazine

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Reaction Steps

3-(5-Bromo-3-methyl-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo-[1,2-b]pyridazine (0.98 g, 2.51 mmol) and 1-methyl-1H-imidazole (0.2 mL), Pd(OAc)2 (34 mg, 0.15 mmol), PPh3 (79 mg, 0.299 mmol), Cs2CO3 (1.95 g, 6.0 mmol) in DMF (50 mL) is stirred under N2 at 130-140° C. overnight. The reaction mixture is cooled, diluted with EtOAc (300 mL), washed with H2O (3×100 mL); dried (Na2SO4); filtered and concentrated. Purification of the resulting crude material by chromatography yields the title compound (0.51 g, 1.29 mmol, 51%). 1H NMR (CDCl3): δ 0.89 (t, J=7.5 Hz, 6H), 1.77-1.92 (m, 4H), 2.17 (s, 3H), 2.51 (s, 3H), 2.54 (s, 3H), 3.30-3.40 (m, 1H), 3.81 (s, 3H), 6.69 (s, 1H), 7.02 (s, 1H), 7.24 (s, 1H), 7.52 (s, 1H). ES-MS (m/z): calcd for C22H27N5S (M+H)+: 394.6; found: 394.3.

Provenance & Evidence