Chloroacetyl chloride → 1-{5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl}-2-chloroethan-1-one

HRID 85079Notes

Reaction equation

HRID 85079 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1.[Cl:15][CH2:16][C:17](Cl)=[O:18]>ClCCl>[Br:5][C:6]1[CH:7]=[C:8]2[C:14]([C:17](=[O:18])[CH2:16][Cl:15])=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 866916611-{5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl}-2-chloroethan-1-oneYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of AlCl3 (3.38 g, 25.38 mmol) in dichloromethane (100 mL) was added 5-Bromo-1H-pyrrolo[2,3-b]pyridine (1 g, 5.07 mmol). After stirring for 30 min, chloroacetyl chloride (2.84 g, 25.38 mmol) was added and the reaction mixture was stirred for 2 hours at room temperature. On completion, solvents were evaporated and quenched with aq. NaHCO3 solution at 0° C. Resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and filtered through a plug of silica gel. Solvent was evaporated to dryness to give 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-chloro-ethanone (1.3 g, 93% yield).

Workup

  1. stirringthe reaction mixture was stirred for 2 hours at room temperature
  2. customOn completion, solvents were evaporated
  3. customquenched with aq. NaHCO3 solution at 0° C
  4. customResulting mixture
  5. extractionwas extracted with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered through a plug of silica gel
  8. customSolvent was evaporated to dryness

Sources & evidence

ORD record
ord-a325c144295b4ec4a459997d424859ba
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

Loading…