Aluminum(III) Chloride → 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(2,3-difluoro-phenyl)-ethanone

HRID 269502Notes

Reaction equation

HRID 269502 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10](Cl)=[O:11].[Br:13][C:14]1[CH:15]=[C:16]2[CH:22]=[CH:21][NH:20][C:17]2=[N:18][CH:19]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[C:16]2[C:22]([C:10](=[O:11])[CH2:9][C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])=[CH:21][NH:20][C:17]2=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 25110985(2,3-Difluorophenyl)acetyl chloride

Product 1

HCID 598322721-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(2,3-difluoro-phenyl)-ethanoneYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,3-Difluorophenylacetyl chloride(58.1 mmol) in CH2Cl2 (150 ml)was added to a suspension of 5-bromo-1H-pyrrolo[2,3-b]pyridine (8.0 g, 40.6 mmol) and AlCl3 (46 g, 345 mmol) in CH2Cl2 (100 ml) at 0° C. After the addition, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hrs. The reaction was cooled with ice-bath and methanol (100 ml) was added to the reaction mixture while maintaining the temperature below 30° C. The reaction mixture was evaporated and the residue was suspended in water. The solid was collected by vacuum filtration, washed with water and hexane to give the title compound (14.03 g) in 98% yield.

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. temperatureThe reaction was cooled with ice-bath
  4. additionmethanol (100 ml) was added to the reaction mixture
  5. temperaturewhile maintaining the temperature below 30° C
  6. customThe reaction mixture was evaporated
  7. filtrationThe solid was collected by vacuum filtration
  8. washwashed with water and hexane

Sources & evidence

ORD record
ord-69dd17d9e2724ff79096b64984e8a2a4
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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