N-Iodosuccinimide → 3-iodo-5-(3,4,5-trimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 333188Notes

Reaction equation

HRID 333188 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[C:15]3[CH:21]=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[I:22]N1C(=O)CCC1=O>CC(C)=O>[I:22][C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:14]=2)[NH:19][CH:20]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 667787825-(3,4,5-trimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 667794073-iodo-5-(3,4,5-trimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridineYield 118.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-(3,4,5-trimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine (510 mg, 1.79 mmol) in acetone (100 ml) was added N-iodosuccinimide (444 mg, 1.97 mmol) under stirring. After 1 hr the mixture was evaporated and purified by silica gel chromatography using 0-2% MeOH:DCM to give the title compound (870 mg, 118%). MS ESI (m/z): 411.1 (M+1)+, calc. 410.

Workup

  1. customAfter 1 hr the mixture was evaporated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3a722f4be67d4faa92b3e1e3534ed6f4
Source dataset
uspto-grants-2014_11
Patent number
US08877772B2

Reaction notes

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