Cesium carbonate → N-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

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Reaction Steps

To a stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (1.47 g, 7.25 mmol, 1.0 eq.) in 25 ml of MeCN was added Cs2CO3 (2.59 g, 7.97 mmol, 1.1 eq.) followed by KI (0.120 g, 0.725 mmol, 0.1 eq.) in one portion. The resulting suspension was stirred for 5 mins before addition of 2-bromo-4-(bromomethyl)-5-methyl-1,3-thiazole (1.96 g, 7.25 mmol, 1 eq.) in one portion. The reaction was stirred for 24 hrs at room temperature. The solvent was evaporated and the residue was dissolved in EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give N-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (2.92 g, 97% yield, 93:7 mixture of stereoisomers) as a white solid.

Provenance & Evidence