Réaction #84081

ord-db93af6d91654f03b6b7fb5890d4bc56

Équation de réaction

COc1ccc2nc(-c3ccc(C#N)cc3)cc(Cl)c2c1
4-(4-chloro-6-methoxyquinolin-2-yl)benzonitrile
[Cs+].[F-]
CsF
COc1ccc2nc(-c3ccc(C#N)cc3)cc(F)c2c1
desired product
Rendement 31.7%
COc1ccc2nc(-c3ccc(C#N)cc3)cc(F)c2c1
4-(4-fluoro-6-methoxyquinolin-2-yl)benzonitrile
Rendement 31.7%

Solvants

Conditions de réaction

Température
150°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreAn aqueous/EtOAC workup was followed by purification by column chromatography (PE/EA=10/1)

Mode opératoire

A mixture of 4-(4-chloro-6-methoxyquinolin-2-yl)benzonitrile (Seem Example 11, step 1) (1 g, 3.4 mmol), CsF (5.2 g, 34 mmol), and n-Bu4NBr (109 mg, 0.34 mmol) in DMSO (10 mL) was heated to 150° C. for 2 h. An aqueous/EtOAC workup was followed by purification by column chromatography (PE/EA=10/1) to afford desired product (300 mg, 31.7%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09433618B2uspto-grants-2016_09