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

Participants

Reaction Steps

A solution of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.10 g, 0.29 mmol), 1,5-dimethyl-1H-indole-2-boronic acid (0.060 g, 0.32 mmol), 2M Na2CO3 (0.22 mL, 0.44 mmol), and n-PrOH (1.5 mL) is degassed with nitrogen for 10 minutes. Pd(OAc)2 (0.0013 g, 0.0058 mmol), and PPh3 (0.0046 g, 0.017 mmol) are added and the solution is heated at a reflux for two 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 (30%-50% EtOAc gradient) to furnish the title compound (0.010 g, 0.028 mmol, 10%). 1H NMR (CDCl3), δ 0.90 (t, J=7.5 Hz, 6H), 1.75-1.95 (m, 4H), 2.48 (s, 3H), 2.49 (s, 3H), 2.51 (s, 3H), 3.32-3.41 (m, 1H), 3.58 (s, 3H), 6.59 (s, 1H), 6.70 (s, 1H), 7.12 (dd, J=8.4, 1.8 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.47 (s, 1H) ppm. LC/MS (m/z): calcd. for C23H28N4 (M+H)+: 361.6; found: 361.2.

Provenance & Evidence