Phosphorus tribromide → HCID 68880465, compound

HRID 2112395Notes

Reaction equation

HRID 2112395 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].P(Br)(Br)[Br:17]>C(#N)C>[Br:17][CH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 61206961HCID 61206961, compound

Product 1

HCID 68880465HCID 68880465, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.813 g (3.94 mmol) 6-(3-hydroxypropyl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione in 10 ml acetonitrile were added dropwise 0.854 g (3.15 mmol) PBr3 and the mixture was heated to reflux for 2 hours. The mixture was concentrated in vacuo and 6 ml of cold water were added to the residue. The precipitate was filtered, washed with cold water and dried in vacuo to get 0.71 g (71%) of the desired product as a light yellow powder. 1H-NMR (DMSO): 2.10-2.23 (m, 2H), 3.52-3.63 (m, 2H), 3.70-3.82 (m, 2H), 7.72-7.81 (m, 1H), 8.22-8.33 (m, 1H), 8.91-9.00 (m, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe mixture was concentrated in vacuo and 6 ml of cold water
  4. additionwere added to the residue
  5. filtrationThe precipitate was filtered
  6. washwashed with cold water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-167d8a6110ab4e6f8720f0b9ff4ce69d
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

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