N-bromobutanimide → HCID 22627433, compound

HRID 1108706Notes

Reaction equation

HRID 1108706 reaction equation
[C:1]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:19][CH2:20][CH3:21])(=[O:5])[CH:2]([CH3:4])[CH3:3].[Br:22]N1C(=O)CCC1=O.N(C(C)(CC(OC)(C)C)C#N)=NC(C)(CC(C)(OC)C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:22][CH:19]([C:7]1[NH:8][C:9]2[C:14]([C:6]=1[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[CH:13][CH:12]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:10]=2)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 22627360HCID 22627360, compound

Product 1

HCID 22627433HCID 22627433, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 3-isobutyryl-2-propylindole-6-carboxylate (201 mg) in carbon tetrachloride (7 ml) was added N-bromosuccinimide (187 mg) and 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) (20 mg) and refluxed for 30 minutes. The resulting mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (2:1) to give methyl 2-(1-bromopropyl)-3-isobutyrylindole-6-carboxylate (179 mg).

Workup

  1. temperaturerefluxed for 30 minutes
  2. filtrationThe resulting mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-17a11f3e3d964fb49499bec7e8734e18
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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