Methyl 5-bromo-2-chloronicotinate → HCID 68008409, Verbindung

HRID 533145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533145
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:13]([B-](F)(F)F)=[CH2:14].[K+]>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Br:1])[CH:3]=[N:4][C:5]=1[CH:13]=[CH2:14]

Komponenten

5

Edukt 2

HCID 2763343Methyl 5-bromo-2-chloronicotinateHCID 23679353Potassium vinyltrifluoroborate

Produkt 1

HCID 68008409HCID 68008409, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl 5-bromo-2-chloronicotinate (500 mg, 2.0 mmol) was dissolved in EtOH (20 mL) with potassium vinyltrifluoroborate (269 mg, 2.0 mmol), TEA (0.28 mL, 2.0 mmol), and [1,1′-Bis (diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (29 mg, 0.04 mmol). The reaction was heated at 80° C. for 1 h, filtered through a Celite pad. The filtrate was concentrated, partitioned between EtOAc (50 mL) and H2O (50 mL). The organic layer was separated, dried over MgSO4 and concentrated. Purification over silica gel using automated flash chromatography (EtOAc/hexanes 0-20%) affords the compound, methyl-5-bromo-2-vinylnicotinate, as a white solid (484 mg, 76%). LC-MS (M+H)=242.1.

Aufarbeitung

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between EtOAc (50 mL) and H2O (50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification over silica gel using automated flash chromatography (EtOAc/hexanes 0-20%)

Quellen und Nachweise

ORD-Eintrag
ord-fddfa0fbe793432fa1738d92589172dc
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853237B2

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