Sodium Carbonate → HCID 10156337, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.05 g, 0.19 mmol), 3-[2-chloro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]pyridine (84 mg, 0.28 mmol) and 2 M Na2CO3 (0.28 ml) in 1,2-dimethoxyethane (2 ml) was degassed for 10 min with a stream of nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.011 g) was added and the mixture was stirred under nitrogen at 80° C. for 12 h. After allowing to cool to ambient temperature, the mixture was diluted with ethyl acetate then partitioned between water (100 ml) and ethyl acetate (100 ml). The organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 3% MeOH/CH2Cl2), to give 75 mg (61%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.42-7.45 (1H, m), 7.71 (1H, d, J 8.6 Hz), 7.86-7.89 (1H, m), 8.08 (1H, dd, J 8.6, 2.5 Hz), 8.14 (1H, d, J 2.5 Hz), 8.64 (1H, s), 8.70 (1H, dd, J 4.9, 2.3 Hz), 8.68 (1H, s), 8.82 (1H, dd, J 2.3, 1.0 Hz); MS (ES+) m/z 376.

Provenance & Evidence