1H-Pyrrolo(2,3-b)pyridine → 2-(2,3-Difluoro-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone

HRID 269478Notes

Reaction equation

HRID 269478 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl>[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:22][C:23]([C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:24]

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 6451240Aluminum(III) ChlorideHCID 25110985(2,3-Difluorophenyl)acetyl chloride

Product 1

HCID 692078882-(2,3-Difluoro-phenyl)-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanoneYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 7-azaindole (1 g, 8.5 mmol) and AlCl3 (1.2 g, 9.0 mmol) in methlene chloride at 0° C. was added (2,3-difluorophenyl)-acetyl chloride [prepared by treating (2,3-difluoro-phenyl)-acetic acid (1.5 mg, 8.72 mmol) with oxalyl chloride (0.90 mL)] in methlene chloride. After stirring at room temperature for 2 hours, the solution was poured into ice water and extracted with methlene chloride, dried (Na2SO4), and concentrated to give 300 mg (13% yield) of title compound used without purification. LCMS Rt=3.00 minutes, MH+ 273.1, M− 271.1.

Workup

  1. extractionextracted with methlene chloride
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5ed0173ba89f407a903578dedc6ec0a3
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

Loading…