N-bromobutanimide → HCID 22627433, compound

HRID 278092Notes

Reaction equation

HRID 278092 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.COC(C)(C)CC(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 21987547HCID 21987547, compoundHCID 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. temperature(20 mg) and refluxed 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-5e97b41888c6418a8601fea5685b8980
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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