Dimethylformamide → HCID 69896330, 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 (300 mg) (prepared as in Example 4), zinc cyanide (187 mg), and DMF (5 ml) was degassed with a stream of N2 for 0.5 h. Tetrakis(triphenylphosphine) palladium(0) (20 mg) was added and the reaction heated to 80° C. for 2 days. The reaction mixture was cooled, poured into 10% ammonium hydroxide solution and extracted into EtOAc, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica, eluting with 50% EtOAc/hexane, and recrystallised from EtOAc/hexane to give the title compound (15 mg, 6%). 1H NMR (360 MHz, CDCl3) δ 8.28 (1H, s), 7.69 (1H, dd, J=8.0, 1.4 Hz), 7.54–7.50 (2H, m), 7.48–7.39 (4H, m), 4.05 (2H, s), 2.73 (3H, s), m/z (ES+) 340 (M+H)+.

Provenance & Evidence