Azobisisobutyronitrile → HCID 90404280, compound

HRID 1505659Notes

Reaction equation

HRID 1505659 reaction equation
[C:1]([C:3]1[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:5]2[C:10]([CH:11]=1)=[C:9]([O:12][CH3:13])[C:8]([CH3:14])=[CH:7][CH:6]=2)#[N:2].[Br:22]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:14][C:8]1[C:9]([O:12][CH3:13])=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:3]([C:1]#[N:2])=[CH:11]2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 90404947HCID 90404947, compound

Product 1

HCID 90404280HCID 90404280, compoundYield 119%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 561 mg of tert-butyl 2-cyano-4-methoxy-5-methyl-1H-indole-1-carboxylate (1.96 mmol) in carbon tetrachloride (9 mL) was added 349 mg of N-bromosuccinimide (1.96 mmol) and 64 mg of AIBN (0.39 mmol). The mixture was refluxed for 1 h, then cooled and concentrated and filtered through short silica gel plug using hexane-ethyl acetate 10:1 to give 852 mg of crude tert-butyl 5-(bromomethyl)-2-cyano-4-methoxy-1H-indole-1-carboxylate that was used in the next step without further purification.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. filtrationfiltered through short silica gel plug

Sources & evidence

ORD record
ord-061259343eb343d6840f12f313fa78e6
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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