Chloroacetyl chloride → 2-Chloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

HRID 731605Notes

Reaction equation

HRID 731605 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Cl:10][CH2:11][C:12](Cl)=[O:13].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[Cl:10][CH2:11][C:12]([C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:13]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 127782172-Chloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A mixture of 7-azaindole (10 g) and chloroacetyl chloride (7.4 mL, 1.1 eq.) are dissolved in carbon disulfide, treated with aluminum chloride (85 g, 7.5 eq.), heated at reflux temperature for 2 h, treated with chloroacetyl chloride (7.4 mL, 1.1 eq.), continued heating at reflux temperature for a further 2 h, cooled to room temperature and decanted to remove the solvent. The sediment is cooled to 0° C., quenched with ice water, treated with sodium carbonate to pH 9 and extracted with EtOAc. The extracts are combined, dried over MgSO4 and concentrated in vacuo to give the title ethanone, 12.5 g (75% yield), identified by HPLC and mass spectral analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 h
  3. temperaturecontinued heating
  4. temperatureat reflux temperature for a further 2 h
  5. customdecanted
  6. customto remove the solvent
  7. temperatureThe sediment is cooled to 0° C.
  8. customquenched with ice water
  9. additiontreated with sodium carbonate to pH 9
  10. extractionextracted with EtOAc
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5117d6c88794407caa9434d51ae92d9a
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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