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Cesium carbonate → Tert-butyl (3-fluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-phenyl)-carbamate

HRID 13290
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 13290
Cl[C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN1CCCC1=O.[F:25][C:26]1[CH:27]=[C:28]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH:29]=[CH:30][C:31]=1[OH:32]>C(OCC)(=O)C>[F:25][C:26]1[CH:27]=[C:28]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH:29]=[CH:30][C:31]=1[O:32][C:2]1[CH:7]=[N:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 11708410tert-Butyl (3-Fluoro-4-hydroxyphenyl)carbamateHCID 231452295-chloro-2-(methylsulfonyl)Pyridine

Produkt 1

HCID 86619205Tert-butyl (3-fluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-phenyl)-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857
Ethyl Acetate
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4.00 g of 5-chloro-2-methanesulfonyl-pyridine and 8.80 g of cesium carbonate were added to an N-methylpyrrolidinone (50 ml) solution of 4.74 g of tert-butyl (3-fluoro-4-hydroxy-phenyl)-carbamate obtained in (step 1), and the reaction liquid was stirred at 100° C. for 2 hours. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1) to obtain the entitled compound.

Aufarbeitung

  1. customobtained in (step 1)
  2. customthe reaction liquid
  3. customThe reaction liquid
  4. washwashed with water and saturated saline in order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1)
  8. customto obtain the entitled compound

Quellen und Nachweise

ORD-Eintrag
ord-f25b9b9defd24663b180c955f8b5d0f7
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728025B2

Notizen zur Reaktion

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