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

HRID 21322

Reaction equation

HRID 21322 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-5a7c56d56b3b4a7793e205a9f0ed7e46
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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