Iodine → 7-Iodo-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinone

HRID 21197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21197
N[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[C:14]([O:26][CH3:27])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[I-:28].[K+].II.[N+]([O-])(OC(C)(C)C)=O>C(#N)C.[Cu](I)I>[I:28][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][Si:19]([C:22]([CH3:24])([CH3:23])[CH3:25])([CH3:21])[CH3:20])=[C:14]([O:26][CH3:27])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Komponenten

7

Edukt 4

HCID 807IodineHCID 4875Potassium IodideHCID 164756Nitric acid, 1,1-dimethylethyl esterHCID 68490965HCID 68490965, Verbindung

Produkt 1

HCID 684891037-Iodo-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinoneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 4 of Example 140, 7-amino-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinone (43.0 mg, 0.110 mmol) was dissolved in acetonitrile (6 mL), and the solution was treated with potassium iodide (29.2 mg, 0.176 mmol), copper iodide (33.5 mg, 0.896 mmol), iodine (44.7 mg, 0.896 mmol) and tert-butyl nitrate (0.059 mL, 0.50 mmol), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=5/1) to obtain 7-iodo-4-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)isoindolinone (33.8 mg, yield 62%).

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-100dff266892419abdae4dd1417ca2ae
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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