Nitrogen → 3-(1,5-dimethyl-1H-indol-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

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Reaction Conditions

Reaction Steps

A solution of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.30 g, 0.87 mmol), 7-isopropyl-1,2-dimethyl-1H-indole (0.33 g, 1.76 mmol), Cs2CO3 (0.57 g, 1.75 mmol), and DMF (5 mL), is degassed with N2 for 20 minutes. Pd2(dba)3 (0.040 g, 0.044 mmol is added and the solution is heated at 130° C. overnight. The solution is diluted EtOAc (30 mL) washed with water (2×30 mL), brine (30 mL) dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (20%-30% EtOAc gradient) to furnish the title compound (0.017 g, 0.042 mmol, 4.8%). 1H NMR (CDCl3), δ 1.14-1.46 (m, 6H), 1.76-1.95 (m, 4H), 2.30 (s, 3H), 2.42 (s, 3H), 2.45 (s, 3H), 3.38-3.48 (m, 1H), 3.86-3.97 (m, 1H), 4.04 (s, 3H), 6.64 (s, 1H), 6.99-7. LC/MS (m/z): calcd. for C26H34N4 (M+H)+: 403.3. found: 403.4.

Provenance & Evidence