Potassium Carbonate → 4-Chloro-5-[3-methyl-3-(triethylsiloxy)butoxy]-7-iodoisoindolinone

HRID 21322

Reaktionsgleichung

Reaktionsgleichung von HRID 21322
[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][C:23]([CH3:33])([O:25][Si:26]([CH2:31][CH3:32])([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:24]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[C:10]([O:11][CH2:21][CH2:22][C:23]([CH3:33])([O:25][Si:26]([CH2:27][CH3:28])([CH2:31][CH3:32])[CH2:29][CH3:30])[CH3:24])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11208288(4-Bromo-2-methyl-2-butoxy)triethylsilaneHCID 684892494-Chloro-5-hydroxy-7-iodoisoindolinone

Produkt 1

HCID 684902934-Chloro-5-[3-methyl-3-(triethylsiloxy)butoxy]-7-iodoisoindolinoneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a similar manner to Step 1 of Example 429, 4-chloro-5-hydroxy-7-iodoisoindolinone (70.8 mg, 0.229 mmol) was dissolved in DMF (2.1 mL), and the solution was treated with potassium carbonate (94.8 mg, 0.686 mmol), tetrabutylammonium iodide (8.5 mg, 0.023 mmol) and (4-bromo-2-methyl-2-butoxy)triethylsilane (193 mg, 0.686 mmol), followed by purification by flash column chromatography (chloroform/methanol=99/1) to obtain 4-chloro-5-[3-methyl-3-(triethylsiloxy)butoxy]-7-iodoisoindolinone (40.7 mg, yield 35%).

Aufarbeitung

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=99/1)

Quellen und Nachweise

ORD-Eintrag
ord-5a7c56d56b3b4a7793e205a9f0ed7e46
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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