Benzoyl chloride → (5-bromo-1H-pyrrolo[2,3-b]pyridine-3-yl)-phenyl-methanone

HRID 901408Notes

Reaction equation

HRID 901408 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.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[Br:5][C:6]1[CH:7]=[C:8]2[C:14]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:22])=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 11301059(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-yl)-phenyl-methanoneYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of AlCl3 (338 mg, 2.54 mmol) in dichloromethane (10 mL) was added 5-bromo-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.507 mmol). After stirring for 45 min, benzoyl chloride (0.3 mL, 2.54 mmol) was added and the reaction mixture was stirred for 3 h, before quenching with MeOH at 0° C. The mixture was concentrated in vacuum, the pH was changed to 4 by addition of 1N aqueous NaOH, and the aqueous layer was extracted twice with EtOAc. The organic layer was dried over MgSO4, filtered and adsorbed on silica gel. Purification on silica gel with a gradient of EtOAc/hexanes afforded (5-bromo-1H-pyrrolo[2,3-b]pyridine-3-yl)-phenyl-methanone as a white solid (61 mg, 40% yield).

Workup

  1. stirringthe reaction mixture was stirred for 3 h
  2. custombefore quenching with MeOH at 0° C
  3. concentrationThe mixture was concentrated in vacuum
  4. additionthe pH was changed to 4 by addition of 1N aqueous NaOH
  5. extractionthe aqueous layer was extracted twice with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customPurification on silica gel with a gradient of EtOAc/hexanes

Sources & evidence

ORD record
ord-db4582f2b8474f6d954bd1e1ae16d4a8
Source dataset
uspto-grants-2008_04
Patent number
US07361763B2

Reaction notes

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