1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178419306, Verbindung

HRID 2246616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246616
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:18]2[CH2:22][CH2:21][O:20][CH2:19]2)=[N:9][NH:10]C(OC(C)(C)C)=O)=[C:4](F)[CH:3]=1.N12CCCN=C1CCCCC2>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:8]([CH:18]3[CH2:22][CH2:21][O:20][CH2:19]3)=[N:9][NH:10]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 724574151,1-Dimethylethyl 2-[(4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methylidene]hydrazinecarboxylate2×

Produkt 1

HCID 178419306HCID 178419306, VerbindungAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 1,1-dimethylethyl 2-[(4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methylidene]hydrazinecarboxylate (Intermediate 8, 1.1 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (424 μL) in tetrahydrofuran (12 mL) in a sealed vial was heated in a microwave oven at 150° C. for 30 min. The reaction mixture was partitioned between ethyl acetate (15 mL) and water (15 mL) and the organic layer was dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified by chromatography on a silica column, eluting with a cyclohexane:ethyl acetate gradient, to give the title compound as a colourless glass (405 mg).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate (15 mL) and water (15 mL)
  2. customthe organic layer was dried
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by chromatography on a silica column
  5. washeluting with a cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-034bdf1948b0458a8404be38db15ffde
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687532B2

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