Water → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(1-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-imidazo[1,2-b]pyridazine

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Reaction Steps

A solution of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine 1-methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (example Rupp-30) (0.23 g, 0.89 mmol), 2M Na2CO3 (0.72 mL, 1.45 mmol), and 7:3:2 DME:Water: EtOH (5 mL) is degassed with nitrogen for 15 minutes. Pd(PPh3)4 (0.051 g, 0.044 mmol) is added and the solution is heated at a reflux for three days. The solution is diluted with CH2Cl2 (50 mL), washed with 10% Na2CO3 (30 mL), water (30 mL), brine (30 mL), dried over MgSO4, filtered and concentrated. The material is purified by ISCO (15%-30% EtOAc gradient) to furnish the title compound (0.12 g, 0.35 mmol, 48%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.78-1.95 (m, 4H), 2.50 (s, 3H), 2.53 (s, 3H), 3.32-3.40 (m, 1H), 3.74 (s, 3H), 6.64 (s, 1H), 6.72 (s, 1H), 7.11 (dd, J=8.3, 4.8 Hz, 1H), 7.96 (dd, J=8.3, 1.3 Hz, 1H), 8.40 (dd, J=4.8, 1.3 Hz, 1H) ppm. LC/MS (m/z): calcd. for C21H25N5 (M+H)+: 348.3. found: 348.2.

Provenance & Evidence