Water → (5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(4-methoxyphenyl)methanone

HRID 1964987Notes

Reaction equation

HRID 1964987 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[N:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]2[C:9]([C:21]([C:20]3[CH:24]=[CH:25][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)=[O:22])=[CH:10][NH:11][C:12]2=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 58086686(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(4-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Aluminum trichloride (2.7 g, 20.0 mmol) and methylene chloride (30 mL) were combined under an atmosphere of nitrogen and 5-bromo-7-azaindole (67, 400.0 mg, 2.30 mmol) in methylene dichloride (20 mL) was added. The reaction was stirred at room temperature for 70 minutes. 4-Methoxybenzoic acid chloride (0.38 g, 2.2 mmol) (prepared from the corresponding carboxylic acid using the protocol described in Example 1, Scheme 13, Step 4) in methylene dichloride (7.0 mL) was added. The reaction was stirred at room temperature for 2 hours, then poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to give the compound (116, 250 mg, 34%).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred at room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give the compound (116, 250 mg, 34%)

Sources & evidence

ORD record
ord-1ae06467944846b9b454bfe45d491af4
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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