Acetyl chloride → 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

HRID 1625999Notes

Reaction equation

HRID 1625999 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1.[C:15](Cl)(=[O:17])[CH3:16]>ClCCl>[Br:5][C:6]1[CH:7]=[C:8]2[C:14]([C:15](=[O:17])[CH3:16])=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 596999141-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum trichloride (846 mg) was added to a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (250 mg) in dichloromethane (5 ml) at room temperature over 10 minutes. Subsequently, acetyl chloride (135 μl) was added and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into ice-cold water and separated by adding dichloromethane. The resulting organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with methanol-chloroform) to give the title compound (186 mg).

Workup

  1. additionThe reaction solution was poured into ice-cold water
  2. customseparated
  3. additionby adding dichloromethane
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developed with methanol-chloroform)

Sources & evidence

ORD record
ord-dfb41c31d324476ca83ad3e7883e5a81
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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