Water → 5-bromo-1H-pyrrolo[2,3-b]pyridine

HRID 2080011Notes

Reaction equation

HRID 2080011 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][C:5]2=[N:6][CH:7]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 219640795-Bromo-2,3-dihydro-7-azaindole

Product 1

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Bromo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (600 mg, 3.01 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone described in Preparation Example R-4 (753 mg, 3.31 mmol) was dissolved in toluene (15 mL), and the solution was refluxed for 40 minutes under nitrogen atmosphere. The reaction solution was cooled to room temperature, water and ethyl acetate were added thereto, the organic layer was partitioned, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (260 mg, 1.32 mmol, 44%) was obtained as a white solid.

Workup

  1. temperaturethe solution was refluxed for 40 minutes under nitrogen atmosphere
  2. customthe organic layer was partitioned
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-b3ddf08283cf40da83ec17afbeaba1f0
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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