Iodine → 3-Amino-6-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]phtalimide

HRID 21106Notes

Reaction equation

HRID 21106 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].[I:29]I.O>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]3[C:20]([C:21]=2[I:29])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

Participants

6

Reactant 3

HCID 807IodineHCID 962WaterHCID 684928123-Amino-6-[1-(tert-butoxycarbonyl)indol-2-yl]phthalimide

Product 1

HCID 684887473-Amino-6-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]phtalimideYield 82%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

3-Amino-6-[1-(tert-butoxycarbonyl)indol-2-yl]phtalimide (300 mg, 0.795 mmol) was dissolved in ethanol (21 mL), and the solution was added with iodine (242 mg, 0.954 mmol) and silver sulfate (248 mg, 0.795 mmol), followed by stirring at room temperature for 1.3 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by slurry using chloroform to obtain 3-amino-6-[1-(tert-butoxycarbonyl)-3-iodoindol-2-yl]phtalimide (326 mg, yield 82%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by slurry

Sources & evidence

ORD record
ord-3a4194fa02704c5cae6b287a0ac883f5
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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