Pyridine → HCID 60004122, Verbindung

HRID 2183458

Reaktionsgleichung

Reaktionsgleichung von HRID 2183458
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[OH:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[N:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>[Cu](I)I.C(N(CC)CC)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:18][C:19]2[CH:24]=[N:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridineHCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

Produkt 1

HCID 60004122HCID 60004122, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A mixture of (S)-[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (10 g, 33.3 mol), 5-hydroxy-2-methylpyridine (4 g, 36.7 mol), copper iodide (6.3 g, 33.3 mol), potassium carbonate (9.2 g, 66.7 mol) and pyridine (33 mL) in sealed tube was heated at 145° C. for six days. The reaction was cooled down to room temperature and filtered, the filtrate was washed with H2O and extracted with CH2Cl2 three times, and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 30:20:1/Hexane:EtOAc:triethylamine to give the title product (3.8 g, 33% yield) as sticky yellow oil.

Aufarbeitung

  1. temperatureThe reaction was cooled down to room temperature
  2. filtrationfiltered
  3. washthe filtrate was washed with H2O
  4. extractionextracted with CH2Cl2 three times
  5. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 30:20:1/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-0bf77f5291be4eca96399512bad071f4
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900210B2

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