tert-Butyl acrylate → HCID 71089237, Verbindung

HRID 1907696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907696
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=2)=[N:6][CH:7]=1.[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH:19]=[CH2:20].CCN(C(C)C)C(C)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2](/[CH:20]=[CH:19]/[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:3][CH:4]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Komponenten

6

Edukt 3

HCID 15458tert-Butyl acrylateHCID 81531DiisopropylethylamineHCID 139797415-Bromo-2-(3,4-dimethoxyphenyl)pyridine

Produkt 1

HCID 71089237HCID 71089237, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a degassed solution of bromide 37 (0.47 g, 1.6 mmol), tert-butyl acrylate 38 (1.12 mL, 7.7 mmol), POT (0.34 g, 1.1 mmol) and Hunig's base (1.11 mL, 6.4 mmol) in DMF (8 mL) was added tris(dibenzylideneacetone)dipalladium (0) (0.124 g, 0.16 mmol). The solution was placed in a preheated oil bath at 120° C., stirred for 18 h and concentrated. Flash chromatography purification of the residue (eluent: 3:1 hexane:AcOEt) afforded title compound 39 (0.45 g, 83% yield).

Aufarbeitung

  1. customThe solution was placed in a preheated oil bath at 120° C.
  2. concentrationconcentrated
  3. customFlash chromatography purification of the residue (eluent: 3:1 hexane:AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-1ca91cccfd9c4f6c8d6b576871167ee0
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598168B2

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