Dibutyltin oxide → HCID 178466679, Verbindung

HRID 510843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510843
[C:1]([C:4]1[CH:5]=[C:6]([Cl:20])[C:7]([CH3:19])=[C:8]([C:17]#[N:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=[O:3])[CH3:2].[N:21]([Si](C)(C)C)=[N+:22]=[N-:23].C([Sn](CCCC)=O)CCC>C1(C)C=CC=CC=1>[Cl:20][C:6]1[C:7]([CH3:19])=[C:8]([C:17]2[NH:23][N:22]=[N:21][N:18]=2)[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

Komponenten

5

Edukt 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 583684696-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile

Produkt 1

HCID 178466679HCID 178466679, VerbindungAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 6-acetyl-4-chloro-3′-fluoro-3-methylbiphenyl-2-carbonitrile (100 mg, 0.3 mmol), azidotrimethylsilane (0.092 mL, 0.69 mmol), and dibutyloxostannane (13 mg, 0.052 mmol) in toluene (2.9 mL) was heated at reflux overnight. The mixture was evaporated to dryness and purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the desired product (85 mg, 70%). LCMS calculated for C16H13ClFN4O (M+H)+: m/z=331.1. found: 331.0.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe mixture was evaporated to dryness
  4. custompurified on silica gel
  5. washeluting with 0 to 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-ec571eb1cb6548bab1984680df6919c1
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096600B2

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