3-(Tributylstannyl)pyridine → HCID 69895842, 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 (100 mg) (as prepared in Example 4), 3-(tri-n-butylstannyl)pyridine (442 mg) and DMF (5 ml) was degassed with a stream of N2 for 0.5 h. Bis(triphenylphosphine)palladium(II) chloride (5 mg) was added and the reaction heated to 100° C. for 2 h. The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica, eluting with 2.5% MeOH/CH2Cl2 to give the title compound (75 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 8.66 (1H, t, J=3.3 Hz), 8.23 (1H, d, J=1.4 Hz), 7.95–7.92 (1H, m), 7.63 (1H, dd, J=8.0, 1.7 Hz), 7.57–7.54 (2H, m), 7.49–7.38 (5H, m), 4.07 (2H, s), 3.97 (2H, s), 2.73 (3H, s), m/z (ES+) 392 (M+H)+.

Provenance & Evidence