Cesium carbonate → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-{2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl}imidazo[1,2-b]pyridazine

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Reaction Conditions

Reaction Steps

A mixture containing 2,6-dimethyl-imidazo[1,2-b]pyridazine (0.44 g, 2.99 mmol), 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.03 g, 2.99 mmol), 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 (0.37 g, 1.02 mmol, 34%). 1H NMR (CDCl3): δ 0.92 (t, J=7.1 Hz, 6H), 1.80-1.95 (m, 4H), 2.43 (s, 3H), 2.44 (s, 3H), 2.46 (s, 3H), 2.50 (s, 3H), 3.35-3.43 (m, 1H), 6.69 (s, 1H), 6.92 (d, J=9.2 Hz, 1H), 7.82 (d, J=1H) ppm. ES-MS (m/z): calcd for C21H26N6 (M+H)+: 363.5. found: 363.3.

Provenance & Evidence