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

HRID 901413Notes

Reaction equation

HRID 901413 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.[Br:15][CH2:16][C:17](Cl)=[O:18]>ClCCl>[Br:15][CH2:16][C:17]([C:14]1[C:8]2[C:9](=[N:10][CH:11]=[C:6]([Br:5])[CH:7]=2)[NH:12][CH:13]=1)=[O:18]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 597000532-Bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

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 30 min, bromoacetyl chloride (0.21 mL, 2.54 mmol) was added and the reaction mixture was stirred for 2 h, before quenching with MeOH at 0° C. The mixture was concentrated in vacuo, the pH was changed to 7 by addition of a saturated solution of aqueous sodium bicarbonate, and the aqueous layer was extracted twice with EtOAc. The organic layer was dried over MgSO4 and filtered through a plug of silica gel. Solvent was evaporated to dryness to give 2-bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone as a light yellow solid (160 mg, quantitative). 1H NMR (500 MHz, DMSO-d6) δ 4.70 (s, 2H), 8.44 (d, J=2.0 Hz, 1H), 8.55 (d, J=2.5 Hz, 1H), 8.68 (d, J=3.5 Hz, 1H), 12.9 (s, 1H). MS: m/z 316 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. custombefore quenching with MeOH at 0° C
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe pH was changed to 7 by addition of a saturated solution of aqueous sodium bicarbonate
  5. extractionthe aqueous layer was extracted twice with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered through a plug of silica gel
  8. customSolvent was evaporated to dryness

Sources & evidence

ORD record
ord-aaf17c7cf9e348828fc44729a207c26c
Source dataset
uspto-grants-2008_04
Patent number
US07361763B2

Reaction notes

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