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Cesium carbonate → HCID 66748949, Verbindung

HRID 537076
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 537076
I[C:2]1[N:3]=[C:4]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([NH:27][C:28](=[O:30])[CH3:29])[CH:21]=2)[O:5][C:6]=1[C:7]1[N:11]=[CH:10][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:8]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[S:73]1(=[O:79])(=[O:78])[CH2:77][CH2:76][CH2:75][NH:74]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[O:78]=[S:73]1(=[O:79])[CH2:77][CH2:76][CH2:75][N:74]1[C:2]1[N:3]=[C:4]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([NH:27][C:28](=[O:30])[CH3:29])[CH:21]=2)[O:5][C:6]=1[C:7]1[N:11]=[CH:10][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:19])[CH3:18])[N:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 6421571,3-PropanesultamHCID 66749237HCID 66749237, Verbindung

Produkt 1

HCID 66748949HCID 66748949, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of N-{4-[4-iodo-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (0.33 g, 0.601 mmol) in 1,4-dioxane (4 mL) was added tris(dibenzylideneacetone)dipalladium(0) (0.055 g, 0.060 mmol), Xantphos (0.10 g, 0.18 mmol), isothiazolidine 1,1-dioxide (0.36 g, 3.01 mmol) and cesium carbonate (0.98 g, 3.00 mmol). The mixture was degassed with nitrogen and then subjected to microwave irradiation at 140° C. for 2.5 h. The mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-{4-[4-(1,1-dioxidoisothiazolidin-2-yl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide which was used directly in the next step. LCMS (FA): m/z=534.6 (M+H).

Aufarbeitung

  1. customThe mixture was degassed with nitrogen
  2. customirradiation at 140° C. for 2.5 h
  3. additionThe mixture was diluted with water
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4dffa67bb41646a69903286ef42f3ac4
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08859768B2

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