1,2,4,5-Tetrazine → 4-(2-Fluoro-5-nitrophenyl)-5-trimethylsilanylpyridazine

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Reaction Steps

(2-Fluoro-5-nitrophenylethynyl)trimethylsilane (8.8 g, 37.1 mmol) and 1,4-dioxane were added to a solution of 1,2,4,5-tetrazine (35 ml, 18.6 mmol, 0.53 M in dichloromethane). The dichloromethane was distilled off and the dioxane solution was stirred at reflux for 36 hours. The solvent was removed to leave a brown oil. Purification by chromatography on silica gel eluting with dichloromethane, then with dichloromethane containing 1% methanol, gave 4-(2-fluoro-5-nitrophenyl)-5-trimethylsilanylpyridazine as a brown oil: m/z (ES+) 292 (M++H) and 249 (M+-3CH2).

Provenance & Evidence