Iodine → 4-Chloro-7-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]isoindolinone

HRID 21108

Reaction equation

HRID 21108 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:27].[I:28]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[C:13]3[C:18]([C:19]=2[I:28])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:27]

Participants

5

Reactant 2

HCID 807IodineHCID 684875944-Chloro-7-(1-(tert-butoxycarbonyl)indol-2-yl)isoindolinone

Product 1

HCID 684922044-Chloro-7-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]isoindolinoneYield 36%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

In a similar manner to Step 1 of Example 161, 4-chloro-7-(1-(tert-butoxycarbonyl)-indol-2-yl)isoindolinone (374 mg, 0.980 mmol) was dissolved in ethanol (26 mL), and the solution was treated with iodine (299 mg, 1.18 mmol) and silver sulfate (306 mg, 0.980 mmol), followed by purification by slurry using hexane and diisopropylether to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]isoindolinone (179 mg, yield 36%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-e091ca1a6fd64562984b79a3781fd88c
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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