Sodium Carbonate → HCID 178515654, Verbindung

HRID 384131

Reaktionsgleichung

Reaktionsgleichung von HRID 384131
Cl[C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][N:20]=[C:19]([OH:22])[CH:18]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(COC)OC>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[O:21][N:20]=[C:19]([OH:22])[CH:18]=4)=[CH:13][CH:12]=3)[CH:5]=[CH:4][CH:3]=2)=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 178515655HCID 178515655, Verbindung

Produkt 1

HCID 178515654HCID 178515654, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22508344DME dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 5-(4-(2-(6-chloropyridin-2-yl)ethoxy)phenyl)isoxazol-3-ol (46.5 mg) in dimethoxyethane ethylene glycol dimethyl ether (3 ml), 18 mg of tetrakis triphenylphosphine palladium, 31 mg of 4-fluorophenylboronic acid and 0.2 ml of 2M aqueous sodium carbonate solution were added, and the reaction solution was stirred at 90° C. for 2 hours. The reaction solution was cooled, then diluted with a saturated saline solution, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid). The solvent of the resultant fraction was diluted with ethyl acetate, washed with saturated sodium bicarbonate water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., methanol/chloroform (1:9)) to afford the title compound as a brown solid.

Aufarbeitung

  1. temperatureThe reaction solution was cooled
  2. additiondiluted with a saturated saline solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid)
  8. additionThe solvent of the resultant fraction was diluted with ethyl acetate
  9. washwashed with saturated sodium bicarbonate water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationThe solvent was distilled off under reduced pressure
  12. customthe residue obtained
  13. customwas purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., methanol/chloroform (1:9))

Quellen und Nachweise

ORD-Eintrag
ord-d0326201dd334b81a4ca02e7f930a220
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367708B2

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