Nitrogen → HCID 89501016, Verbindung

HRID 63820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63820
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[C:4](I)[CH:3]=1.N#N.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19]>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[C:4](/[CH:19]=[CH:18]/[C:17]([O:21][CH3:22])=[O:20])[CH:3]=1

Komponenten

6

Edukt 3

HCID 947NitrogenHCID 7294Methyl AcrylateHCID 89501076HCID 89501076, Verbindung

Produkt 1

HCID 89501016HCID 89501016, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of Intermediate 5B (100 g, 324.4 mmol) in ACN (1000 mL) was degassed with N2. TEA (64 mL) and methyl acrylate (60 mL) were added and the reaction was further degassed. Pd(OAc)2 (8 g, 11.8 mmol) was added and the reaction was heated to 85° C. for 18 h. The reaction was concentrated and the residue was diluted with H2O. The aqueous layer was extracted with EtOAc and the combined organics were washed with brine. Purification by silica gel chromatography gave 25 g Intermediate 5C. MS (ESI) m/z: 283.0 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. additionthe residue was diluted with H2O
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organics were washed with brine
  5. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fd09aa0ac2784d3f90edebe4b7ed06e9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447110B2

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