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

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Reaction Conditions

Reaction Steps

To a dry 10 ml round bottom flask with reflux condenser containing 8-(1-ethyl-propyl)-6-methyl-2-trifluoromethyl-imidazo[1,2-b]pyridazine (300 mg, 1.11 mmol), 2-bromo-3-methyl-thiophene (216 mg, 1.22 mmol), and Cs2CO3 (760 mg, 2.33 mmol) is added NMP (1.7 ml). The mixture is degassed with bubbling N2 for 15 min and Pd2(dba)3 (50.8 mg, 0.055 mmol) and PPh3 (58.2 mg, 0.222 mmol) are added. The reaction mixture is stirred at 130° C. overnight. The mixture is cooled to rt, diluted with H2O; and extracted with EtOAc (3×20 ml). The organic layers are dried (Na2SO4), filtered and purified by HPLC to give title compound (32 mg, 0.087 mmol, 8%). 1H-NMR (CDCl3), δ 0.93 (t, J=7.2 Hz, 6H), 1.91 (m, 4H), 2.15 (s, 3H), 2.58 (s, 3H), 3.36 (m, 1H), 6.91 (s, 1H), 7.08 (d, J=5.3 Hz, 1H), 7.55 (d, J=5.5 Hz, 1H) ppm. ES-MS (m/z): calcd for C19H20F3N3S (M+H)+: 367.44; found: 368.1.

Provenance & Evidence