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

HRID 21197Notes

Reaction equation

HRID 21197 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-100dff266892419abdae4dd1417ca2ae
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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