N-Iodosuccinimide → 2-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole

HRID 1043656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043656
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[S:11][C:10]3=[N:12][CH:13]=[CH:14][N:9]3[N:8]=2)=[CH:4][CH:3]=1.[I:17]N1C(=O)CCC1=O>CN(C)C=O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[S:11][C:10]3=[N:12][CH:13]=[C:14]([I:17])[N:9]3[N:8]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 673361162-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole

Produkt 1

HCID 673357762-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazoleAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole (0.6 g, 2.55 mmol) was dissolved in N,N-dimethylformamide (10 mL) and N-iodosuccinimide (0.63 g, 2.81 mmol) was added in one portion. The reaction mixture was stirred at room temperature overnight in the absence of light. The yellow suspension was filtered and rinsed with diethylether (2×2 mL) to give 2-(4-fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (0.65 g, 71%). The filtrate was evaporated and the residue was triturated with diethylether (6 mL) and filtered. This solid was purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0:10 to 1:9) to give 2-(4-fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (0.15 g, 16% yield).

Aufarbeitung

  1. filtrationThe yellow suspension was filtered
  2. washrinsed with diethylether (2×2 mL)

Quellen und Nachweise

ORD-Eintrag
ord-cdcd5fb59e744bbaadba6bad0d80bda9
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563550B2

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