Azobisisobutyronitrile → HCID 22648068, compound

HRID 394170Notes

Reaction equation

HRID 394170 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:20])[N:9]2[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[N:3]=1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]2[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=2[F:28])[N:3]=1

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 22647989HCID 22647989, compound

Product 1

HCID 22648068HCID 22648068, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a refluxing solution of 7-bromo-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-1,6-naphthyridin-2(1H)-one (0.747 g) and AIBN (0.03 g) in 30 mL of CCl4 was added recrystallized N-bromosuccinimide (0.302 g). The reaction was stirred at reflux for 1 h, then removed from the heat. DBU (0.23 mL) was added and the mixture was stirred at rt for 15 min. The reaction mixture was washed with 100 mL of saturated sodium bicarbonate and back extracted with 50 mL of dichloromethane. The combined organics were washed with 100 mL of brine, dried with sodium sulfate, and concentrated to give the desired product. Mass spectrum m/z (ESI) 481.3 (M+1).

Workup

  1. customrecrystallized N-bromosuccinimide (0.302 g)
  2. temperatureat reflux for 1 h
  3. customremoved from the heat
  4. additionDBU (0.23 mL) was added
  5. stirringthe mixture was stirred at rt for 15 min
  6. washThe reaction mixture was washed with 100 mL of saturated sodium bicarbonate
  7. extractionback extracted with 50 mL of dichloromethane
  8. washThe combined organics were washed with 100 mL of brine
  9. dry with materialdried with sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d7e669cfbe944e7bab77bada42a5f0de
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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