Iodine → 7-Iodo-4-(4-tert-butyldimethylsilyloxyphenyl)isoindolinone

HRID 21200Notes

Reaction equation

HRID 21200 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])=[CH:14][CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[I-:26].[K+].II.[N+]([O-])(OC(C)(C)C)=O>C(#N)C.[Cu](I)I>[I:26][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])=[CH:14][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 684900227-Amino-4-(4-tert-butyldimethylsilyloxyphenyl)isoindolinone

Product 1

HCID 684894227-Iodo-4-(4-tert-butyldimethylsilyloxyphenyl)isoindolinoneYield 47%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 4 of Example 140, 7-amino-4-(4-tert-butyldimethylsilyloxyphenyl)isoindolinone (179 mg, 0.505 mmol) was dissolved in acetonitrile (12.5 mL), and the solution was treated with potassium iodide (133 mg, 0.808 mmol), copper iodide (152 mg, 0.808 mmol), iodine (203 mg, 0.808 mmol) and tert-butyl nitrate (0.127 mL, 1.06 mmol), followed by purification by flash column chromatography (chloroform) to obtain 7-iodo-4-(4-tert-butyldimethylsilyloxyphenyl)isoindolinone (109 mg, yield 47%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform)

Sources & evidence

ORD record
ord-9c45ea9b5aba425d9edc19e430596f45
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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