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Cesium fluoride → 5-(2-Chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ol

HRID 335093
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 335093
Br[C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)[O:25]1.C1(P(C2CCCC2)C2CCCC2)CCCC1.[F-].[Cs+]>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:15][C:4]1[CH:3]=[C:2]([OH:25])[CH:7]=[N:6][C:5]=1[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH3:14])[N:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 25953Cesium fluorideHCID 2733548Bis(pinacolato)diboraneHCID 4463278Phosphine, tricyclopentyl-HCID 24764526N-(5-bromo-3-(2-chlorophenylthio)pyridin-2-yl)-4-methylthiazol-2-amine

Produkt 1

HCID 247645195-(2-Chlorophenylthio)-6-(4-methylthiazol-2-ylamino)pyridin-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysator
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A degassed mixture of N-(5-bromo-3-(2-chlorophenylthio)pyridin-2-yl)-4-methylthiazol-2-amine (1.10 g, 2.66 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.35 g, 5.32 mmol), Pd(OAc)2 (60 mg, 0.27 mmol), tricyclopentylphosphine (93 mg. 0.40 mmol) and cesium fluoride (3.64 g, 23.9 mmol) in acetonitrile is heated at 90° C. for 5 hours. The reaction mixture is cooled and partitioned between ether and water. The crude product is dissolved in THF. N-morpholine N-oxide (1.40 g, 12.0 mmol) is added and the reaction mixture is heated at reflux for 12 hours. The reaction mixture is cooled and partitioned between ether and water: The organic layer is washed with water and brine, dried and concentrated. The residue is purified by silica gel chromatography, eluting with 10-20% EtOAc in hexanes to afford the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. custompartitioned between ether and water
  3. dissolutionThe crude product is dissolved in THF
  4. temperaturethe reaction mixture is heated
  5. temperatureat reflux for 12 hours
  6. temperatureThe reaction mixture is cooled
  7. custompartitioned between ether and water
  8. washThe organic layer is washed with water and brine
  9. customdried
  10. concentrationconcentrated
  11. customThe residue is purified by silica gel chromatography
  12. washeluting with 10-20% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b35f712f56d0415f809078ec32764091
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883828B2

Notizen zur Reaktion

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