Cesium carbonate → HCID 69895797, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromo-3-(5-methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (220 mg) (prepared as in Example 4), 4-pyridylboranic acid (295 mg), Cs2CO3 (1.26 g/l ml H2O), and DME (3 ml) was degassed with a stream of N2 for 0.5 h. Bis(triphenylphosphine)palladium(II) chloride (42 mg) was added and the reaction heated to 100° C. for 5 h. The reaction mixture was cooled, poured into H2O and extracted into CH2Cl2, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica, eluting with 3% MeOH/CH2Cl2, and recrystallised from CH2Cl2/hexane to give the title compound (50 mg, 21%). 1H NMR (360 MHz, CDCl3) δ 8.72 (2H, d, J=4.5 Hz), 8.29 (1H, d, J=1.3 Hz), 7.67 (1H, dd, J=8.0, 1.7 Hz), 7.57–7.53 (4H, m), 7.48–7.39 (4H, m), 4.07 (2H, s), 2.73 (3H, s), m/z (ES+) 392 (M+H)+.

Provenance & Evidence