Methyl 2-acetamidoacrylate → 2-Acetylamino-3-(2-[1,3]dioxan-2-yl-3-fluoro-phenyl)-acrylic acid methyl ester

HRID 2245284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245284
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[C:3]=1[CH:9]1[O:14][CH2:13][CH2:12][CH2:11][O:10]1.[CH3:15][O:16][C:17](=[O:24])[C:18]([NH:20][C:21](=[O:23])[CH3:22])=[CH2:19].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:15][O:16][C:17](=[O:24])[C:18]([NH:20][C:21](=[O:23])[CH3:22])=[CH:19][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH:9]1[O:14][CH2:13][CH2:12][CH2:11][O:10]1

Komponenten

7

Edukt 3

HCID 98644Methyl 2-acetamidoacrylateHCID 516892Sodium BicarbonateHCID 685501032-(2-Fluoro-6-iodo-phenyl)-[1,3]dioxane

Produkt 1

HCID 685501862-Acetylamino-3-(2-[1,3]dioxan-2-yl-3-fluoro-phenyl)-acrylic acid methyl esterAusbeute 12,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A DMF (10 ml) solution of 2-(2-fluoro-6-iodo-phenyl)-[1,3]dioxane (1.85 g, 6 mmol), 2-acetylamino-acrylic acid methyl ester (906 mg, 6.33 mmol), sodium bicarbonate (1.26 g, 15 mmol), tetrabutyl ammonium chloride (1.35 g, 4.86 mmol) and palladium (II) acetate (52 mg, 0.23 mmol) is heated at 90° C. for 1.8 hours. The reaction mixture is poured onto water and the aqueous phase is extracted with ethylacetate. The organic layer is washed with brine and dried over MgSO4 and evaporated. The crude product is purified by chromatography (CH2Cl2/MeOH, 95/5) to afford the desired compound (240 mg). MS (ES+): m/e=346.3, (MNa+)

Aufarbeitung

  1. additionThe reaction mixture is poured onto water
  2. extractionthe aqueous phase is extracted with ethylacetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product is purified by chromatography (CH2Cl2/MeOH, 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-381a067d5259455dae0a8904179e7689
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683075B2

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