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Cesium carbonate → Ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate

HRID 537034
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 537034
[Br:1][C:2]1[O:3][C:4](Br)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:28]([NH:27][C:23]1[CH:22]=[C:21]([C:4]2[O:3][C:2]([Br:1])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=2)[CH:26]=[CH:25][N:24]=1)(=[O:30])[CH3:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 49760417N-(4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamideHCID 53216927Ethyl 2,5-dibromofuran-3-carboxylate

Produkt 1

HCID 66748312Ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoateAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 962WaterLösungsmittel2×
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2,5-dibromo-3-furoate (0.21 g, 0.722 mmol) in 1,4-dioxane (2.2 mL) and water (0.50 mL) were added tetrakis(triphenylphosphine) palladium(0) (0.08 g, 0.07 mmol), N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (0.19 g, 0.72 mmol) and cesium carbonate (0.71 g, 2.2 mmol). The reaction mixture was subjected to microwave irradiation at 95° C. for 15 min. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give ethyl 5-[2-(acetylamino)pyridin-4-yl]-2-bromo-3-furoate (0.035 g, 14%) as a white solid. LCMS (FA): m/z=339.1 (M+H).

Aufarbeitung

  1. customirradiation at 95° C. for 15 min
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-15b71ea8d78444dea49ff0abc2951521
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08859768B2

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