Methyl Acrylate → Ethyl (2E)-3-(5-formyl-2-pyridinyl)-2-propenoate

HRID 43356

Reaktionsgleichung

Reaktionsgleichung von HRID 43356
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].[C:16]1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(=O)C.[Na+]>CN(C=O)C.[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]>[CH:8]([C:5]1[CH:6]=[CH:7][C:2](/[CH:12]=[CH:11]/[C:10]([O:14][CH2:15][CH3:16])=[O:13])=[N:3][CH:4]=1)=[O:9]

Komponenten

7

Edukt 4

HCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 517045Sodium AcetateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Produkt 1

HCID 86628160Ethyl (2E)-3-(5-formyl-2-pyridinyl)-2-propenoateAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 2-bromo-5-formylpyridine (500 mg, 2.6 mmol), methyl acrylate (0.6 ml, 6.5 mmol), tri-(o-tolyl)phosphine (80 mg, 0.26 mmol), allyl palladium (II) chloride dimer (47 mg, 0.13 mmol) and sodium acetate (1.08 g, 8 mmol) in DMF (10 ml) was heated at 170° C. in a microwave reactor for 0.75 h. The reaction mixture was filtered through Celite® then diluted with DCM and water. The organic phase was dried, concentrated in vacuo and purified by chromatography to give the title compound as a white solid (50 mg). δH (CDCl3, 250 MHz) 10.14 (1H, s), 9.09 (1H, d), 8.19 (1H, dd), 7.72 (1H, d), 7.57 (1H, d), 7.08 (1H, d), 3.85 (3H, s). MS (ES): MH+ 192.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite®
  2. additionthen diluted with DCM and water
  3. customThe organic phase was dried
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c0809180160c4ca9954d8ce9512a8b6f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536182B2

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