Cesium carbonate → (2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol

HRID 70526

Reaktionsgleichung

Reaktionsgleichung von HRID 70526
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:36][C:37]1[CH:38]=[CH:39][C:40](/[C:45](/I)=[CH:46]/[CH2:47][OH:48])=[N:41][C:42]=1[O:43][CH3:44]>O1CCOCC1.C(OCC)(=O)C.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>[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[C:45](/[C:40]2[CH:39]=[CH:38][C:37]([Cl:36])=[C:42]([O:43][CH3:44])[N:41]=2)=[CH:46]\[CH2:47][OH:48])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 521585Tris(furan-2-yl)phosphaneHCID 27343204-tert-Butylphenylboronic acidHCID 58452855(2Z)-3-(5-Chloro-6-methoxypyridin-2-yl)-3-iodoprop-2-en-1-ol

Produkt 1

HCID 58452849(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-olAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

4-tert-Butylphenylboronic acid (3.5 g), tris(dibenzylideneacetone)dipalladium(0) (183 mg), tri(2-furyl)phosphine (280 mg) and cesium carbonate (1.98 g) were added to a solution of (2Z)-3-(5-chloro-6-methoxypyridin-2-yl)-3-iodoprop-2-en-1-ol (881 mg) in 1,4-dioxane (20 mL)-water (10 mL) in a nitrogen atmosphere, and the mixture was stirred at an external temperature of 65° C. for 1.5 hours. The reaction solution was left to cool, diluted with ethyl acetate and filtered. The filtrate was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→1:1) to give the title compound as a light yellow powder (912 mg, 91%).

Aufarbeitung

  1. waitThe reaction solution was left
  2. temperatureto cool
  3. filtrationfiltered
  4. washThe filtrate was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-08a57a96d9184121a1cb0aadff6dac11
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

Verknüpfte Notizen

Wird geladen…