Trimethylsilyl iodide → 5-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide

HRID 1053155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053155
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([CH:18]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([O:16]C)[CH:11]=1)=[O:8].[Si](I)(C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([CH:18]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=1)=[O:8]

Komponenten

4

Edukt 2

HCID 85247Trimethylsilyl iodideHCID 867284685-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide

Produkt 1

HCID 867284695-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamideAusbeute 26,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 5-chloro-2-fluoro-N-(2-methoxy-4-pyridyl)benzamide (3.8 g, 13.50 mmol) in acetonitrile (126.3 mL) was added TMSI (7.7 mL, 54.00 mmol). The reaction was stirred at 50° C. overnight. The acetonitrile was evaporated and the crude re-dissolved in ethyl acetate. The organics were washed with water, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography using a gradient of ethyl acetate in hexanes (0-100%) and then methanol in dichloromethane (0-20%) yielded 5-chloro-2-fluoro-N-(2-oxo-1H-pyridin-4-yl)benzamide (950 mg, 26%) as a white solid. ESI-MS m/z calc. 266.03. found 267.1 (M+1)+; Retention time: 1.24 minutes (3 minutes run).

Aufarbeitung

  1. customThe acetonitrile was evaporated
  2. dissolutionthe crude re-dissolved in ethyl acetate
  3. washThe organics were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f1ecf1195e48462189d9e1c445ffe586
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393235B2

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