Azobisisobutyronitrile → 6-(1-Bromoethyl)pyridine-3-carbonitrile

HRID 512508Notes

Reaction equation

HRID 512508 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1)[CH3:2].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl>[Br:11][CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 181776766-Ethylpyridine-3-carbonitrile

Product 1

HCID 867115466-(1-Bromoethyl)pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 6-ethyl-nicotinonitrile (synthesis described in WO2008/71404, 1000 mg, 7.57 mmol), N-bromosuccinimide (1632 mg, 9.08 mmol) and 2,2′-azo-bis(isobutyronitrile) (62 mg, 0.38 mmol) in chloroform (12 mL) is heated at reflux for 7 min. After cooling to room temperature, the reaction mixture is filtered and the volatiles are removed under reduced pressure (260 mbar, 55° C.) to yield the product which was used without further purification. Yield: 1597 mg (quant.); ESI mass spectrum: [M+H]+=211 (Br pattern); Retention time HPLC: 0.92 min (Z018_S04).

Workup

  1. temperatureat reflux for 7 min
  2. filtrationthe reaction mixture is filtered
  3. customthe volatiles are removed under reduced pressure (260 mbar, 55° C.)
  4. customto yield the product which
  5. customwas used without further purification
  6. custom0.92 min (Z018_S04)

Sources & evidence

ORD record
ord-7a52b46d21284c2da15510313b90356c
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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