Process for the preparation of polyfluoroalkylated quinolines

Patent metadata

Field	Value
Publication number	US-10266494-B2
Application number	US-201716070561-A
Country	US
Kind code	B2
Filing date	Jan 13, 2017
Priority date	Jan 21, 2016
Publication date	Apr 23, 2019
Grant date	Apr 23, 2019

Abstract

The invention relates to a novel process for preparing polyfluoroalkylated quinolines from ketimines in the presence of fluoroalkylamino reagents.

First claim

The invention claimed is:

1. Process for preparing a quinoline derivative of formula (I)

in which
R 1 is C 1-5 -haloalkyl, aryl,
R 2 is C 1-5 -haloalkyl, C 2-6 -haloalkylhaloalkoxy
and
R 3 , R 4 , R 5 are each independently selected from H, C 1-5 -alkyl, halogen, C 1-5 -haloalkoxy, C 1-6 -alkoxy, aryl, C 1-4 -dialkylamino, C 1-6 -thioalkyl, thioaryl
or R 4 R 5 together form an annulated phenyl
wherein one or more ketimines of formula (II)

in which the radicals are as defined above,
are reacted with one or more fluoroalkylamino reagents of formula (III)

in which
X is F or Cl,
R 6 and R 7 are each independently selected from C 1-6 -alkyl, C 3-8 -cycloalkyl in the presence of Lewis Acid.

2. Process according to claim 1 , wherein
R 1 is CH 2 F, CF 2 H, CF 3 , C 2 F 5 ,
R 2 is CF 2 H, CF 3 , CFHCl, CF 3 CFH, CFHOCF 3 ,
R 3 , R 4 , R 5 are each independently selected from H, halogen, CF 3 O, N(CH 3 ) 2 , phenyl, C 1-6 -thioalkyl, C 6-10 -thioaryl, C 1-6 -alkoxy, aryl, C 1-4 -dialkylamino
or R 4 R 5 together form an annulated phenyl,
X is F,
R 6 , R 7 are each independently selected from CH 3 , C 2 H 5 .

3. Process according to claim 1 , wherein
R 1 is CF 2 H, CF 3 ,
R 2 is CF 2 H, CFHCl, CF 3 CFH, R 3 is H, F, CF 3 , CF 3 O, N(CH 3 ) 2 ,
R 4 is H, F, Cl, OCH 3 , OCF 3 , N(CH 3 ) 2 , CF 3
or R 4 R 5 together form an annulated phenyl,
R 5 is H, OCH 3 , F, OCF 3 , CH 3 , phenyl, thiophenyl,
X is F,
R 6 , R 7 are each independently selected from CH 3 .

4. Process according to claim 1 , in which the Lewis Acid is BF 3 .

5. Process according to claim 1 , in which one or more fluoroalkylamino reagents (III) are first reacted with BF 3 or AlCl 3 and then a compound of formula (II) is added in substance or dissolved in a solvent.

Assignees

• Bayer Cropscience Ag
• Centre Nat Rech Scient

Inventors

• Pazenok Sergii
• Vors Jean-Pierre
• Leroux Frédéric R
• Aribi Fallia
• Schmitt Etienne
• Panossian Armen

Classifications

• C07D215/18 Primary

  Halogen atoms or nitro radicals · CPC title

• C07D221/10

  Aza-phenanthrenes · CPC title

• C07D215/36

  Sulfur atoms (C07D215/24 takes precedence) · CPC title

• C07D215/26

  Alcohols; Ethers thereof · CPC title

• C07D215/20

  Oxygen atoms · CPC title