Sodium Carbonate → HCID 10133067, compound

Participants

Reaction Conditions

Reaction Steps

7-[3-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.2 g, 0.53 mmol) was added to 1,2-dimethoxyethane (2 ml), 2-bromo-5-fluoropyridine (94 mg, 0.53 mmol) and 2 N Na2CO3 (0.53 ml). The mixture was degassed with a stream of nitrogen for 10 min before tetrakis(triphenylphosphine)palladium(0) (31 mg, 0.027 mmol) was added and the mixture heated at 80° C. for 6 h. The mixture was cooled to ambient temperature before partitioning between water (15 ml) and ethyl acetate (15 ml). The organic extracts were then washed with NaOH (15 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography (silica gel, 3% MeOH/CH2Cl2) then triturated with diethyl ether to give 53 mg (28%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.51-7.56 (1H, m), 7.67 (1H, t, J 7.7 Hz), 7.83 (1H, dd, J 9.2, 4.1 Hz), 8.03 (1H, dq, J 7.7, 1.0 Hz), 8.14 (1H, dq, J 7.7, 1.0 Hz), 8.60 (1H, d, J 3.1 Hz), 8.70 (1H, s), 8.72 (1H, t, J 1.6 Hz), 8.84 (1H, s); MS (ES+) m/z 360 [M+H]+.

Provenance & Evidence