Triphenylphosphine → HCID 18399758, compound

HRID 2184814Notes

Reaction equation

HRID 2184814 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:28]([N:35]1[C:43]2[CH:42]=[CH:41][NH:40][C:39](=O)[C:38]=2[CH:37]=[CH:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCOCC1>[CH2:28]([N:35]1[C:43]2[CH:42]=[CH:41][N:40]=[C:39]([Br:1])[C:38]=2[CH:37]=[CH:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 141143851-Benzyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 18399758HCID 18399758, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

35 g of N-bromosuccinimide are added to a solution of 52 g of triphenylphosphine in 1.5 l of dioxane. After stirring the mixture for 1 hour, 9 g of 1-benzyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one in 200 ml of dioxane are added and the mixture is heated at reflux for 15 hours. After removal of the dioxane under reduced pressure, 100 ml of triethylamine are added to the residue and the whole is then concentrated in vacuo. Chromatography on silica gel (cyclohexane/ethyl acetate: 50/50) enables the expected product to be isolated.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 15 hours
  3. customAfter removal of the dioxane under reduced pressure, 100 ml of triethylamine
  4. additionare added to the residue
  5. concentrationthe whole is then concentrated in vacuo
  6. customto be isolated

Sources & evidence

ORD record
ord-9cdedae125094e93af79e9eda3d6e420
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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