N-bromobutanimide → 2-Bromo-4-(5-bromomethyl-3-phenyl-isoxazol-4-yl)-pyridine

HRID 2120863Notes

Reaction equation

HRID 2120863 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:10][O:11][C:12]=2[CH3:13])[CH:5]=[CH:4][N:3]=1.[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:10][O:11][C:12]=2[CH2:13][Br:20])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 234356652-Bromo-4-(5-methyl-3-phenyl-isoxazol-4-yl)-pyridine

Product 1

HCID 234356442-Bromo-4-(5-bromomethyl-3-phenyl-isoxazol-4-yl)-pyridineYield 57%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of the above Compound 17a (404 mg, 1.28 mmol), N-bromosuccinimide (239 mg, 1.35 mmol) and AIBN (11 mg, 0.064 mmol) in CCl4 (3 mL) was heated to reflux and placed under a 300 W lamp for 18 h. The solution was diluted with CH2Cl2 (15 mL), extracted with H2O (3×10 mL), brine (40 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (SiO2, 15-20% EtOAc-hexanes) provided the title compound (287 mg, 0.728 mmol, 57%).

Workup

  1. temperatureto reflux
  2. extractionextracted with H2O (3×10 mL), brine (40 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1118711176dd4ab99b200912856b062e
Source dataset
uspto-grants-2004_02
Patent number
US06693108B2

Reaction notes

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