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1. WO2009003590 - A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH HETEROARYL TOSYLATES AND HETEROARYL BENZENESULFONATES

Publication Number WO/2009/003590
Publication Date 08.01.2009
International Application No. PCT/EP2008/004928
International Filing Date 19.06.2008
Chapter 2 Demand Filed 25.04.2009
IPC
C07D 213/127 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02having three double bonds between ring members or between ring members and non-ring members
04having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
06containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
127Preparation from compounds containing pyridine rings
C07D 213/26 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02having three double bonds between ring members or between ring members and non-ring members
04having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
24with substituted hydrocarbon radicals attached to ring carbon atoms
26Radicals substituted by halogen atoms or nitro radicals
C07D 213/30 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02having three double bonds between ring members or between ring members and non-ring members
04having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
24with substituted hydrocarbon radicals attached to ring carbon atoms
28Radicals substituted by singly-bound oxygen or sulfur atoms
30Oxygen atoms
C07D 215/12 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
215Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
12with substituted hydrocarbon radicals attached to ring carbon atoms
C07D 215/14 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
215Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
12with substituted hydrocarbon radicals attached to ring carbon atoms
14Radicals substituted by oxygen atoms
C07D 231/12 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
231Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
02not condensed with other rings
10having two or three double bonds between ring members or between ring members and non-ring members
12with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
CPC
C07D 213/127
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02having three double bonds between ring members or between ring members and non-ring members
04having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
06containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
127Preparation from compounds containing pyridine rings
C07D 213/26
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02having three double bonds between ring members or between ring members and non-ring members
04having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
24with substituted hydrocarbon radicals attached to ring carbon atoms
26Radicals substituted by halogen atoms or nitro radicals
C07D 213/30
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
213Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02having three double bonds between ring members or between ring members and non-ring members
04having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
24with substituted hydrocarbon radicals attached to ring carbon atoms
28Radicals substituted by singly-bound oxygen or sulfur atoms
30Oxygen atoms
C07D 215/12
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
215Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
12with substituted hydrocarbon radicals attached to ring carbon atoms
C07D 215/14
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
215Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
12with substituted hydrocarbon radicals attached to ring carbon atoms
14Radicals substituted by oxygen atoms
C07D 231/12
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
231Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
02not condensed with other rings
10having two or three double bonds between ring members or between ring members and non-ring members
12with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Applicants
  • SANOFI-AVENTIS [FR]/[FR] (AllExceptUS)
  • R'KYEK, Omar [MA]/[MA] (UsOnly)
  • NAZARÈ, Marc [DE]/[DE] (UsOnly)
  • LINDENSCHMIDT, Andreas [DE]/[DE] (UsOnly)
  • ALONSO, Jorge [ES]/[DE] (UsOnly)
  • URMANN, Matthias [DE]/[DE] (UsOnly)
  • HALLAND, Nis [DK]/[DE] (UsOnly)
Inventors
  • R'KYEK, Omar
  • NAZARÈ, Marc
  • LINDENSCHMIDT, Andreas
  • ALONSO, Jorge
  • URMANN, Matthias
  • HALLAND, Nis
Agents
  • THEN, Johann
Priority Data
07290839.503.07.2007EP
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH HETEROARYL TOSYLATES AND HETEROARYL BENZENESULFONATES
(FR) PROCÉDÉ DE COUPLAGE CATALYSÉ PAR LE PALLADIUM D'ALCYNES TERMINALES AVEC DES HÉTÉROARYL TOSYLATES ET DES HÉTÉROARYL BENZÈNESULFONATES
Abstract
(EN)
The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), (I) wherein D, J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process of heteroaryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional heteroaryl-1 -alkynes of the formula I useful for the production of pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.
(FR)
La présente invention concerne un procédé de synthse régiosélective de composés représentés par la formule (I), dans laquelle D, J et W ont les significations indiquées dans les revendications. La présente invention concerne un procédé, efficace et général, de couplage catalysé par le palladium, d'hétéroaryl tosylates avec des alcynes terminales afin d'obtenir une large variété d'hétéroaryl-1-alcynes substituées, multifonctionnelles, représentées par la formule I, utiles pour la production de médicaments, d'agents de diagnostic, de cristaux liquides, de polymères, d'herbicides, de fongicides, de nématicides, de parasiticides, d'insecticides, d'acaricides et d'arthropodicides.
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