Ethyl diazoacetate → ethyl trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazin-4-yl)cyclopropanecarboxylate

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Reaction Steps

A solution of 3-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine (23-3, 530 mg, 2.64 mmol 1.0 eq.) in toluene (35 mL) was refluxed under nitrogen. To the reaction mixture was added ethyl diazoacetate (0.50 mL, 4.75 mmol, 1.8 eq.) dropwise. The mixture was refluxed for 2 hours. The solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (20% acetone in hexanes) to afford ethyl trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazin-4-yl)cyclopropanecarboxylate (23-4) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.95 (d, 1H, J=2.0 Hz), 7.71 (d, 1H, J=2.0 Hz), 4.21 (q, 2H, J=7.2 Hz), 2.93 (s, 3H), 2.56 (m, 1H), 2.43 (s, 3H), 2.16 (m, 1H), 1.82 (m, 1H), 1.51 (m, 1H), 1.30 (t, 3H, J=7.2 Hz).

Provenance & Evidence