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

HRID 1498790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1498790
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:9]=[N:10][CH:11]=[C:12]([CH:14]=[CH2:15])[CH:13]=2)[N:3]=1.[N+](=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N-]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:9]=[N:10][CH:11]=[C:12]([C@@H:14]3[CH2:15][C@H:18]3[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=2)[N:3]=1

Komponenten

4

Edukt 2

HCID 12192Ethyl diazoacetateHCID 867320493-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-5-vinylpyridazine

Produkt 1

HCID 86732050ethyl trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazin-4-yl)cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (20% acetone in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f4d5f3a69e8844ed9d1dceb76eecec5c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200001B2

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