Dimethylformamide → HCID 54112325, compound

HRID 1678134Notes

Reaction equation

HRID 1678134 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7](C)[CH:8]=[O:9].[C:11]1([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH2:19][C:18]2=O)C=CC=CC=1.[OH-].[NH4+]>O.ClCCl.N1C=CC=CC=1>[CH3:11][N:17]([CH:18]=[C:19]1[C:20]2[C:6](=[N:22][CH:23]=[CH:24][CH:25]=2)[NH:7][C:8]1=[O:9])[CH3:21]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 149872061-Phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 54112325HCID 54112325, compoundYield 47.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Phosphorous oxychloride (693 μL, 7.47 mmol) is added slowly to a stirred solution of dimethylformamide (714 μL) and dichloromethane (714 μL) cooled to 0-5° C. After 10 min, a solution of the above 1-phenyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (350 mg, 1.66 mmol), pyridine (357 μL) and dichloromethane (1.43 mL) is added and the reaction is stirred at room temperature for 24 hr. The reaction mixture is poured into water, the pH adjusted to 8 with ammonium hydroxide and extracted with dichloromethane (2×). The combined extract is dried, filtered and concentrated. The residue is purified by chromatography eluting with dichlormethane-2% methanol. Product containing fractions are combined and concentrated to afford 3-dimethylaminomethylene-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (211 mg, 47.9% yield).

Workup

  1. extractionextracted with dichloromethane (2×)
  2. extractionThe combined extract
  3. customis dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography
  7. washeluting with dichlormethane-2% methanol
  8. additionProduct containing fractions
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-df616151b4a6439eb20dc84a62eb1dc7
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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