Water → HCID 58086860, compound

HRID 1964975Notes

Reaction equation

HRID 1964975 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.Cl[C:16]([C:18]1[C:19]([CH3:28])=[C:20]([O:24][C:25](=[O:27])[CH3:26])[CH:21]=[CH:22][CH:23]=1)=[O:17].O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]2[C:9]([C:16]([C:18]3[C:19]([CH3:28])=[C:20]([O:24][C:25](=[O:27])[CH3:26])[CH:21]=[CH:22][CH:23]=3)=[O:17])=[CH:10][NH:11][C:12]2=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 7010345(3-(Chlorocarbonyl)-2-methylphenyl)acetateHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 58086860HCID 58086860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To aluminum trichloride (6.14 g, 0.046 mol) in methylene chloride (26 mL) under an atmosphere of nitrogen was added 5-Bromo-7-azaindole (67, 1.05 g, 5.31 mmol) dissolved in methylene dichloride (20.0 mL). The reaction was stirred at room temperature for 65.0 minutes, then acetic acid 3-chlorocarbonyl-2-methyl-phenyl ester (1.25 g, 5.88 mmol) in methylene dichloride (7.0 mL) was added. The reaction was stirred for 2 hours at room temperature, poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give crude compound 84 that was used directly in the next step.

Workup

  1. stirringThe reaction was stirred for 2 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb66f8d0183d4948b0ce16e781fc96fa
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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