N-Iodosuccinimide → (3-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)(morpholino)methanone

HRID 1820028Notes

Reaction equation

HRID 1820028 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:11]=[C:12]([C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[O:17])[CH:13]=[CH:14][CH:15]=3)[CH:9]=[C:4]2[CH:3]=[CH:2]1.C1C(=O)N([I:31])C(=O)C1>CC(C)=O>[I:31][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([C:10]3[CH:11]=[C:12]([C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[O:17])[CH:13]=[CH:14][CH:15]=3)[CH:9]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 49830767(3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)(morpholino)methanone

Product 1

HCID 59699903(3-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)(morpholino)methanoneYield 77.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)(morpholino)methanone (550 mg, 1.79 mmol) in acetone (10 mL) was added NIS (604 mg, 2.68 mmol) and the mixture was stirred at room temperature for 20 minutes. Acetone was removed by reduced pressure and the crude product was purified by silica gel chromatography to afforded (3-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)(morpholino)methanone (600 mg, 77% yield). MS: m/z 434.2 (M+H+).

Workup

  1. customAcetone was removed by reduced pressure
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d5185923aec44d53af666bce176a8352
Source dataset
uspto-grants-2009_10
Patent number
US07601839B2

Reaction notes

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