Triethylamine → HCID 86666319, Verbindung

HRID 1026337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026337
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C@@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:5][C:4]=1[F:21])#[CH:2].Br[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][N:24]=1.C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:30]([O:29][C:26]1[CH:27]=[CH:28][C:23]([C:2]#[C:1][C:3]2[CH:20]=[CH:19][C:6]([O:7][CH2:8][C@@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])=[CH:5][C:4]=2[F:21])=[N:24][CH:25]=1)[CH3:31]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 234368922-Bromo-5-ethoxypyridineHCID 86666318HCID 86666318, Verbindung

Produkt 1

HCID 86666319HCID 86666319, VerbindungAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under nitrogen, a mixture of tert-butyl [(1S)-2-(4-ethynyl-3-fluorophenoxy)-1-methylethyl]carbamate (9.36 g), 2-bromo-5-ethoxypyridine (5.86 g), bis(triphenylphosphine)palladium(II) dichloride (2.04 g), cuprous iodide (0.552 g), triethylamine (6.06 mL), and toluene (20 mL) was stirred at 100° C. overnight. The precipitate was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (7.00 g) as a yellow solid.

Aufarbeitung

  1. filtrationThe precipitate was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5ef7bfbf3d8e401e8230b7731f82e000
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729102B2

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