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Cesium carbonate → Ethyl 4-(5-(dimethylcarbamoyl)pyrazin-2-yloxy)-2-methylbenzofuran-6-carboxylate

HRID 1253610
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1253610
[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1.Cl[C:18]1[N:19]=[CH:20][C:21]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[N:22][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:27][N:26]([CH3:28])[C:24]([C:21]1[N:22]=[CH:23][C:18]([O:1][C:2]2[C:7]3[CH:8]=[C:9]([CH3:11])[O:10][C:6]=3[CH:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=2)=[N:19][CH:20]=1)=[O:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 11514065Ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylateHCID 590004705-chloro-N,N-dimethylpyrazine-2-carboxamide

Produkt 1

HCID 59483311Ethyl 4-(5-(dimethylcarbamoyl)pyrazin-2-yloxy)-2-methylbenzofuran-6-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

The flask was charged with ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate (I-1c: 6.07 g, 27.6 mmol), 5-chloro-N,N-dimethylpyrazine-2-carboxamide (SM-1: 5.06 g, 27.3 mmol), cesium carbonate (9.78 g, 30 mmol). The solids were dissolved in dimethylformamide (60 mL). The reaction was heated to 90° C. for 3 hours. After the reaction was cooled down to ambient temperature, dimethylformamide was removed in vacuo. The crude reaction mixture was partitioned between ethyl acetate (100 ml) and water (30 mL). The aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layer was washed with water, brine, dried over sodium sulfate, and concentrated. The crude product was purified by column chromatography (silica gel, 30 to 80% gradient of ethyl acetate in heptane) to give desired ethyl 4-(5-(dimethylcarbamoyl)pyrazin-2-yloxy)-2-methylbenzofuran-6-carboxylate (I-1d) as a light brown solid (8.3 g, 95%).

Aufarbeitung

  1. temperatureAfter the reaction was cooled down to ambient temperature
  2. customdimethylformamide was removed in vacuo
  3. customThe crude reaction mixture
  4. customwas partitioned between ethyl acetate (100 ml) and water (30 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
  6. washThe combined organic layer was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (silica gel, 30 to 80% gradient of ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-5dd5f2a82c4a4f5c9a3db41769d2b177
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08455496B2

Notizen zur Reaktion

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