Potassium Carbonate → 4-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-iodoisoindolinone

HRID 21316

Reaction equation

HRID 21316 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]Br)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[C:10]([O:11][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

6

Reactant 3

HCID 11430Potassium CarbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 684892494-Chloro-5-hydroxy-7-iodoisoindolinone

Product 1

HCID 684925174-Chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-iodoisoindolinoneYield 79.7%

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 (100 mg, 0.323 mmol) was dissolved in DMF (3.0 mL), and the solution was treated with potassium carbonate (134 mg, 0.969 mmol), tetrabutylammonium iodide (11.8 mg, 0.032 mmol) and tert-butyl(3-bromopropoxy)dimethylsilane (0.112 mL, 0.485 mmol), followed by purification by flash column chromatography (chloroform/methanol=99/1, 19/1) to obtain 4-chloro-5-[3-(tert-butyldimethylsiloxy)propoxy]-7-iodoisoindolinone (124 mg, yield 79%).

Workup

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

Sources & evidence

ORD record
ord-466c88c3583141a7bc59d2c2395d2f4b
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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