Potassium Carbonate → 4-Chloro-5-[4-(tert-butyldimethylsiloxy)butoxy]-7-iodoisoindolinone

HRID 21320

Reaction equation

HRID 21320 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+].[C:20]([Si:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31]I)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[Cl:1][C:2]1[C:10]([O:11][CH2:31][CH2:30][CH2:29][CH2:28][O:27][Si:24]([C:20]([CH3:21])([CH3:23])[CH3:22])([CH3:25])[CH3:26])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4250746tert-Butyl(4-iodobutoxy)dimethylsilaneHCID 684892494-Chloro-5-hydroxy-7-iodoisoindolinone

Product 1

HCID 684891864-Chloro-5-[4-(tert-butyldimethylsiloxy)butoxy]-7-iodoisoindolinoneYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Example 429, 4-chloro-5-hydroxy-7-iodoisoindolinone (70.0 mg, 0.226 mmol) was dissolved in DMF (2.1 mL), and the solution was treated with potassium carbonate (93.8 mg, 0.679 mmol) and tert-butyl(4-iodobutoxy)dimethylsilane (0.176 mL, 0.679 mmol), followed by purification by flash column chromatography (chloroform/methanol=99/1, 19/1) to obtain 4-chloro-5-[4-(tert-butyldimethylsiloxy)butoxy]-7-iodoisoindolinone (94.2 mg, yield 84%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=99/1, 19/1)

Sources & evidence

ORD record
ord-b55de8f5f3794a9395126dbed7095092
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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