Cesium carbonate → HCID 86650765, compound

Participants

Reaction Steps

To a stirred solution of ((Z)-N-hydroxy-1-(1-methyl-1H-1,2,4-triazol-5-yl)-1-phenylmethanimine (7 g, 34.61 mmol, 1.0 eq.) in 500 ml of MeCN was added Cs2CO3 (12.40 g, 38.07 mmol, 1.1 eq.) followed by Kl (0.575 g, 3.46 mmol, 0.1 eq.) in one portion. The resulting suspension was stirred for 5 mins before addition of 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (10.97 g, 34.61 mmol, 1.0 eq.) in one portion. The reaction was stirred for 4 h at room temperature. The solid was removed by filtration and washed with 250 ml of fresh MeCN. The filtrate was evaporated, and 500 ml of EtOAc were added. The organic layer was washed with H2O and dried over MgSO4 then concentrated. Chromatography of the crude on silica gel gave 2-{6-[({[(1-methyl-1H-1,2,4-triazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione (11.27 g, 74% yield) as a white solid.

Provenance & Evidence