Phosphorus oxybromide → HCID 22503398, compound

HRID 1251123Notes

Reaction equation

HRID 1251123 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)(Br)=O.C(=O)(O)[O-].[Na+].BrC1C=CC(CCCOCC2C=CC=CC=2)=CN=1.BrC1C(CCCOCC2C=CC=CC=2)=CC=CN=1.[CH2:65]([N:67]1[CH2:72][CH2:71][N:70]([C:73]2[C:82]3[C:77](=[CH:78][CH:79]=[CH:80][CH:81]=3)[CH:76]=[C:75](Br)[N:74]=2)[CH2:69][CH2:68]1)[CH3:66]>C(Cl)Cl.O>[CH2:65]([N:67]1[CH2:68][CH2:69][N:70]([C:73]2[C:82]3[C:77](=[CH:78][CH:79]=[CH:80][CH:81]=3)[CH:76]=[C:75]([C:15]3[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][N:14]=3)[N:74]=2)[CH2:71][CH2:72]1)[CH3:66]

Participants

9

Reactant 6

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 20720267HCID 20720267, compoundHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 22503248HCID 22503248, compoundHCID 22503578HCID 22503578, compound

Product 1

HCID 22503398HCID 22503398, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-(3-Benzyloxypropyl)pyridine N-oxide (4.546 g) was dissolved in methylene chloride, phosphorus oxybromide (11.47 g) was added thereto under ice-cooling, and the mixture was stirred for 2 hr. Then, it was further stirred at room temperature for 2 hr. The reaction mixture was poured into warm water, and then it was neutralized by adding sodium bicarbonate thereto. The mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give a mixture of 2-bromo-5-(3-benzyloxypropyl)pyridine and 2-bromo-3-(3-benzyloxypropyl)pyridine (1:1) as a brown oil (2.203 g). The resulting mixture (1.111 g) and 1-(1-ethylpiperazin-4-yl)-3-bromoisoquinoline (662 mg) were treated in the same manner as in Example 167-2, to give the title compound as a yellow oil (326 mg, yield; 33%).

Workup

  1. temperatureunder ice-cooling
  2. stirringThen, it was further stirred at room temperature for 2 hr
  3. additionThe reaction mixture was poured
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe resulting organic layer was washed with water
  6. dry with materialdried (over MgSO4)
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)
  9. customto give

Sources & evidence

ORD record
ord-a924d9af25aa49a1bfd604202807277f
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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