Benzoyl Peroxide → HCID 68442800, compound

HRID 1435874Notes

Reaction equation

HRID 1435874 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=3)[CH:7]=[CH:8][N:9]=2)[N:4]=1.C1C(=O)N([Br:27])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:6]2[CH:7]=[CH:8][N:9]=[C:10]3[C:5]=2[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]3)=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68452792HCID 68452792, compound

Product 1

HCID 68442800HCID 68442800, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2-methoxy-8-(5-methylpyridin-2-yl)[1,5]naphthyridine (1.2 g, 4.78 mmole), in dry CCl4 (150 mL) at RT was added NBS (1.02 g, 5.73 mmole) and benzoylperoxide (0.12 g, 0.48 mmole). After 18 h at reflux, the reaction contents were cooled to RT and filtered through a scintered-glass funnel washing with CHCl3. Concentration under vacuum and purification on silica (EtOAc) afforded the title compound (1.12 g, 71%) as light yellow solid: (EtOAc): LC-MS (ES) m/e 330 (M)+.

Workup

  1. temperatureAfter 18 h at reflux
  2. customthe reaction contents
  3. filtrationfiltered through a scintered-glass funnel
  4. washwashing with CHCl3
  5. concentrationConcentration
  6. customunder vacuum and purification on silica (EtOAc)

Sources & evidence

ORD record
ord-6ca84d0dec5740aeaa225ea2237aa4e7
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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