Phosphorus oxychloride → HCID 57633205, compound

HRID 2108750Notes

Reaction equation

HRID 2108750 reaction equation
P(Cl)(Cl)([Cl:3])=O.[NH:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15](=O)[CH3:16])=[CH:7]1.C[C:19]([O-:21])=O.[Na+]>CN(C=O)C>[Cl:3]/[C:15](/[C:8]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:6][CH:7]=1)=[CH:16]/[CH:19]=[O:21]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 127782161-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

Product 1

HCID 57633205HCID 57633205, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Phosphorous oxychloride (3.7 mL, 40 mmol) was added dropwise to DMF (6.2 mL, 80 mmol) at 0° C. The reaction mixture was let warm to room temperature and stirred for 15 minutes. 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-ethanone was added in DMF (20 mL) and the reaction heated to 60° C. for 4 hours, cooled to 0° C. and 150 mL of saturated NaOAc solution added. The reaction mixture was heated briefly to 50° C. and then extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to an oil which contains impure product. Upon standing a solid precipitated from the aqueous layer to give 0.9 g of a brown solid, 4.3 mmol, 22% yield.

Workup

  1. temperaturethe reaction heated to 60° C. for 4 hours
  2. temperaturecooled to 0° C.
  3. temperatureThe reaction mixture was heated briefly to 50° C.
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to an oil which
  8. customprecipitated from the aqueous layer

Sources & evidence

ORD record
ord-dc77c7cdf3c64a219b4df0a25f10c27a
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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