Phosphorus oxybromide → HCID 9908871, compound

HRID 2268858Notes

Reaction equation

HRID 2268858 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12](=O)[NH:11][N:10]=1.P(Br)(Br)([Br:25])=O>C(#N)C>[Br:25][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[C:9]([CH2:8][C:7]2[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=2[Cl:22])=[N:10][N:11]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 224827114-(3,5-Dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-one

Product 1

HCID 9908871HCID 9908871, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-(3,5-dichloro-pyridin-4-ylmethyl)-7-methoxy-2H-phthalazin-1-one (10 g, 25.5 mmoles), prepared as described in example 38, in acetonitrile (300 ml), was added with POBr3 (22 g, 76.5 mmoles) and the mixture was refluxed. After 1 night under reflux and another to stand, the solution was concentrated, taken up in water, cooled in ice and alkalinised with concentrated NaOH. There was extracted three times with CH2Cl2 and the organic phases were discoloured with charcoal, anhydrified and concentrated. The crude was purified by flash chromatography (eluent: petrolatum/ethyl acetate 8:2, then 6:4) to give 8.4 g of the title compound (yield: 82%).

Workup

  1. customprepared
  2. temperaturethe mixture was refluxed
  3. temperatureAfter 1 night under reflux
  4. concentrationthe solution was concentrated
  5. temperaturecooled in ice
  6. extractionThere was extracted three times with CH2Cl2
  7. concentrationconcentrated
  8. customThe crude was purified by flash chromatography (eluent

Sources & evidence

ORD record
ord-1e76733a6c504c0cb9736758ba89236f
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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