Sodium Bicarbonate → 2-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

HRID 734790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734790
C(=O)(O)[O-].[Na+].Br[C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:15]2[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][OH:22])=[C:17]([CH3:25])[CH:16]=2)=[N:11][CH:12]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](OB(O)O)=[CH:29][CH:28]=1>O1CCOCC1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:15]3[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][OH:22])=[C:17]([CH3:25])[CH:16]=3)=[N:11][CH:12]=2)=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 17810664p-Chlorophenylboric acid2×HCID 690586072-[4-(5-Bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol

Produkt 1

HCID 673624362-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

40 mL of 2 N aqueous sodium bicarbonate solution was added to a suspension of 13.20 g (39.74 mmol) of 2-[4-(5-bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol, 9.32 g (59.60 mmol) of 4-chlorophenylboric acid, and 2.30 g (1.99 mmol) of tetrakis(triphenylphosphane)palladium in 400 mL of 1,4-dioxane and the mixture was refluxed for 12 hours. Another 4.66 g of 4-chlorophenylboric acid and 1.14 g of tetrakis(triphenylphosphane)palladium were added and the mixture was refluxed for 8 hours. The reaction mixture was evaporated down in vacuo and the residue was stirred with EtOAc and water. The precipitate was filtered off, washed with diethyl ether, and dried in vacuo. Yield: 10.70 g (74% of theoretical); C22H18ClNO2 (M=363.837); calc.: molpeak (M+H)+: 364/366 (Cl); found: molpeak (M+H)+: 364/366 (Cl); Rf value: 0.47 (silica gel, DCM/EtOAc 2:1).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 12 hours
  2. temperaturethe mixture was refluxed for 8 hours
  3. customThe reaction mixture was evaporated down in vacuo
  4. filtrationThe precipitate was filtered off
  5. washwashed with diethyl ether
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-71883cc4b6dc4e3096aaa7a0c013533f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592358B2

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