Triethylamine → HCID 53930754, Verbindung

HRID 1108414

Reaktionsgleichung

Reaktionsgleichung von HRID 1108414
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][CH:6](N)[CH:7]=[CH2:8])[CH3:2].[C:11]([O:15][CH2:16]C)(=O)[CH:12]=C.[CH2:18]([N:20](CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][O:15][C:11]1[N:20]=[CH:18][C:7]([CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[O:10])=[CH:8][CH:12]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 10057602Ethyl 3-aminopent-4-enoate

Produkt 1

HCID 53930754HCID 53930754, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of the 5-bromo-2-methoxypyridine 18-2 (74.3 g, 0.4 mol), ethyl acrylate (150 mL, 1.4 mol), triethylamine (150 mL, 1.08 mol), palladium acetate (10 g, 0.045 mol) and tri-o-tolylphosphine (20 g, 0.066 mol) in 100 mL acetonitrile was degassed with argon for 10 minutes. The mixture was heated at 90° C. for 12 hr then the volatiles were removed in vacuo. Toluene (300 mL) was added and the mixture concentrated again. Diethyl ether (300 mL) was added and the mixture filtered through a pad of silica gel eluting with 800 mL of diethyl ether. After removal of the diethyl ether, the residue was chromatographed on silica gel eluting with EtOAc/hexane, 1:19 then 1:14 then 1:9, to give 19-3 as a yellow solid.

Aufarbeitung

  1. customthe volatiles were removed in vacuo
  2. additionToluene (300 mL) was added
  3. concentrationthe mixture concentrated again
  4. additionDiethyl ether (300 mL) was added
  5. filtrationthe mixture filtered through a pad of silica gel eluting with 800 mL of diethyl ether
  6. customAfter removal of the diethyl ether
  7. customthe residue was chromatographed on silica gel eluting with EtOAc/hexane, 1:19

Quellen und Nachweise

ORD-Eintrag
ord-1b8eee3e5b8e4e11bf5d7d06989909b3
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066648

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