1,5-Diazabicyclo(4.3.0)non-5-ene → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.7 g, 3.44 mmol, 1.0 eq.) in 25 ml of MeCN, was added dropwise DBN (0.42 g, 3.44 mmol, 1.0 eq.). The reaction was stirred for 5 mins before addition of 2-bromo-4-(1-bromoethyl)-1,3-thiazole (0.86 g, 3.2 mmol, 0.93 eq.) portionwise. The mixture was stirred for further 5 mins before removal of the cooling bath and continued at ambient temperature. LCMS after 2 h would indicate reaction complete. MeCN was evaporated and the residue was purified by chromatography on silica gel to yield N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (6.9 g, 79% yield, 9:1 mixture of stereoisomers).

Provenance & Evidence