Ethyl Acetate → 5-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridine

HRID 531430Notes

Reaction equation

HRID 531430 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[I:11]N1C(=O)CCC1=O.C(OCC)(=O)C>CC(C)=O.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 120273N-IodosuccinimideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 242292125-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridineYield 87.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

5-Bromo-1H-pyrrolo[2,3-b]pyridine (5 g, 25 mmol) was dissolved in anhydrous acetone (75 ml) and added N-iodo succinimide (6.18 g, 27.5 mmol) under nitrogen atmosphere and stirred at RT for 2 h. The reaction was monitored by TLC (10% Ethyl acetate in hexane). The reaction mixture was cooled to RT and filtered, washed with cold acetone (50 ml) and dried under vacuum to afford 7.05 g (87% yield) of 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. washwashed with cold acetone (50 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-088b0570349d489b98daa88c4df8e4c2
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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