Water → acetic acid 3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2-methyl-phenyl ester

HRID 1261127Notes

Reaction equation

HRID 1261127 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 58086860acetic acid 3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2-methyl-phenyl ester

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-6798c96269444e7fb0910f36ab756518
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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