Chloropyrazine → Tert-butyl 2-(2-pyrazinyl)phenylcarbamate

HRID 1816278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816278
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Sn](C)(C)C)([CH3:4])([CH3:3])[CH3:2].Cl[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu+]>[N:21]1[CH:22]=[CH:23][N:24]=[CH:25][C:20]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 2

HCID 73277ChloropyrazineHCID 10155176(2-Trimethylstannanyl-phenyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 22493234Tert-butyl 2-(2-pyrazinyl)phenylcarbamateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 104815Copper(1+)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(2-Trimethylstannyl-phenyl)-carbamic acid tert-butyl ester (Bioorganic & Medicinal Chemistry,1998, 6,811-823) (1.4 g, 3.93 mmol), 2-chloropyrazine (0.5 g, 4.33 mmol, 1,1 eq), tetrakis(triphenylphosphine)palladium (0.18 g, 0.156 mmol), and copper (I) b (0.022 g, 0.156 mmol), in 1,4-dioxane (10 mL) were heated at 110° C. for 75 min. The reaction mixture was allowed to cool at room temperature. The crude product was adsorbed onto silica gel and purified by column chromatography to give 0.65 g of tert-butyl 2-(2-pyrazinyl)phenylcarbamate.

Aufarbeitung

  1. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c02ebc74b17c4ab48afe454acef111af
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884801B1

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