N-bromobutanimide → 4-(3-bromo-1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole

HRID 241623Notes

Reaction equation

HRID 241623 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[C:18]2[C:26]2[C:27]([CH3:32])=[N:28][O:29][C:30]=2[CH3:31])=[CH:13][CH:12]=1>CN(C=O)C>[Br:8][C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:16][CH:15]=2)[C:18]=1[C:26]1[C:27]([CH3:32])=[N:28][O:29][C:30]=1[CH3:31]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 583782004-(1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole

Product 1

HCID 583782244-(3-bromo-1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazoleYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (59 mg, 0.33 mmol) was added to a cooled (0° C.) solution of 4-(1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole (105 mg, 0.33 mmol) in 5 ml of DMF. The temperature was allowed to warm to RT and the mixture was stirred at RT for 30 min. DMF was evaporated. DCM and water were added and the phases were separated. After evaporation of the solvents, the residue was purified by flash chromatography with heptane/EtOAc 9:1 to provide 4-(3-bromo-1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole in 98% yield. ES/MS m/z: 365.14 (M+H), 363.30 (M−H).

Workup

  1. customDMF was evaporated
  2. additionDCM and water were added
  3. customthe phases were separated
  4. customAfter evaporation of the solvents
  5. customthe residue was purified by flash chromatography with heptane/EtOAc 9:1

Sources & evidence

ORD record
ord-b7ae562d125b49d18c43b1e96e1de755
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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