Iodine → 7-Iodo-4-(3-tert-butyldimethylsilyloxyphenyl)isoindolinone

HRID 21203Notes

Reaction equation

HRID 21203 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[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][CH:15]=[C:14]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[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 684909767-Amino-4-(3-tert-butyldimethylsilyloxyphenyl)isoindolinone

Product 1

HCID 684891857-Iodo-4-(3-tert-butyldimethylsilyloxyphenyl)isoindolinoneYield 52.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a similar manner to Step 4 of Example 140, 7-amino-4-(3-tert-butyldimethylsilyloxyphenyl)isoindolinone (115 mg, 0.324 mmol) was dissolved in acetonitrile (8.0 mL), and the solution was treated with potassium iodide (73.8 mg, 0.441 mmol), copper iodide (84.8 mg, 0.441 mmol), iodine (113 mg, 0.441 mmol) and tert-butyl nitrate (0.071 mL, 0.551 mmol), followed by purification by flash column chromatography (chloroform) to obtain 7-iodo-4-(3-tert-butyldimethylsilyloxyphenyl)isoindolinone (78.6 mg, yield 52%).

Workup

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

Sources & evidence

ORD record
ord-baf5a46fc2234c6eaa9ceb4f2c57f770
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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