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US 2014/0371468 A1Published application
Process for the Preparation of 1-H-pyrrolidine-2,4-dione Derivatives
AssigneeBayer CropScience AG
InventorsReiner FISCHER, Thomas HIMMLER
Life of this patent
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Abstract
The present invention relates to a novel process for the preparation of 1-H-pyrrolidine-2,4-dione derivatives and to novel intermediates and to a process for their preparation.
Claims9
A process for preparing compounds of formula (I)
- in which
- W is hydrogen, halogen, alkyl, alkenyl, alkynyl, optionally substituted cyclocalkyl, alkoxy, haloalkyl or haloalkoxy,
- X is hydrogen, halogen, alkyl, alkenyl, alkynyl, optionally substituted cycloalkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
- Y and Z, independently of one another, are hydrogen, alkyl, alkenyl, alkynyl, halogen, cyano, optionally substituted cycloalkyl, alkoxy, haloalkyl, haloalkoxy or in each case optionally substituted aryl or hetaryl,
- A is hydrogen, is in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl, in which optionally at least one ring atom is replaced by a heteroatom, or aryl, arylalkyl or hetaryl each of which is optionally substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano or nitro,
- B is hydrogen, alkyl or alkoxyalkyl, or
- A and B, together with the carbon atom to which they are bonded are a saturated or unsaturated unsubstituted or substituted cycle optionally containing at least one heteroatom,
- G is hydrogen (a) or is one of the groups
- in which
- E is a metal ion or an ammonium ion,
- L is oxygen or sulphur,
- M is oxygen or sulphur,
- R1 is alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl each of which is optionally substituted by halogen or cyano, or is cycloalkyl or heterocyclyl each of which is optionally substituted by halogen, alkyl or alkoxy, or is in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
- R2 is alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl each of which is optionally substituted by halogen or cyano, or is in each case optionally substituted cycloalkyl, phenyl or benzyl,
- said process comprising:
- reacting a compound of formula (X)
- in which
- A and B have the meanings given above,
- G is the groups a), b), c) and E given above,
- V is hydrogen or
- V is COOR8,
- where R8 is alkyl
- with a compound of the formula (XI)
- in which
- W, X, Y and Z have the meanings given above, with the exception that the halogen can now only be fluorine and chlorine, X may also additionally be hydrogen and
- Q is triflate, bromine or iodine,
- in the presence of a base, a palladium catalyst and a phosphine ligand of the formula (XII′)
- in which the radicals
- R′, R″ and R′″ independently of one another are C1-C12-alkyl, C5-C10-cycloalkyl, C6-C10-aryl, optionally mono- or polysubstituted by C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, C1-C6-dialkylamino or phenyl optionally mono- or polysubstituted by C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino or C1-C6-dialkylamino,
- in a diluent.
27 more elements
A Compound of formula (X)
- in which
- A, B and the carbon atom to which they are bonded are preferably saturated C5-C6-cycloalkyl in which one ring member is replaced by oxygen or sulphur and which is optionally mono- or disubstituted by C1-C6-alkyl or C1-C6-alkoxy or
- A, B and the carbon atom to which they are bonded are preferably C3-C6-cycloalkyl in which optionally one ring member is replaced by nitrogen and which is mono- or disubstituted, independently of one another, by C1-C8-alkyl, C1-C8-alkoxy, halogen, C3-C8-alkenyloxy, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C2-alkoxy, C3-C10-cycloalkyl, C1-C8-haloalkyl, C2-C6-haloalkoxy or C1-C6-alkoxy-C1-C4-alkoxy, where the aforementioned radicals (with the exception of halogen and C1-C8-haloalkyl) are also suitable as N substituents and C1-C8-alkyl is only permitted in the event of a disubstitution, or
- A, B and the carbon atom to which they are bonded are C5-C6-cycloalkyl which is substituted by an alkylenediyl group or by an alkylenedioxyl group or by an alkylenedithioyl group which optionally contains one or two non-directly adjacent oxygen and/or sulphur atoms and which is optionally substituted by C1-C4-alkyl, and which, with the carbon atom to which it is bonded, forms a further five- to eight-membered ring,
- G is hydrogen (a) or is one of the groups
- in which
- E is a metal ion or an ammonium ion
- R1 is C1-C8-alkyl, C2-C8-alkenyl, C1-C4-alkoxy-C1-C2-alkyl, C1-C4-alkylthio-C1-C2-alkyl each of which is optionally mono- to trisubstituted by fluorine or chlorine, or C3-C6-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C1-C2-alkyl or C1-C2-alkoxy, in which optionally one or two non-directly adjacent ring members are replaced by oxygen,
- is phenyl optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkyl or C1-C2-haloalkoxy,
- R2 is C1-C8-alkyl, C2-C8-alkenyl or C1-C4-alkoxy-C2-C4-alkyl each of which is optionally mono- to trisubstituted by fluorine,
- is C3-C6-cycloalkyl optionally monosubstituted by C1-C2-alkyl or C1-C2-alkoxy or
- is phenyl or benzyl each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, C1-C3-alkoxy, trifluoromethyl or trifluoromethoxy,
- V is hydrogen (X-1) or COOR8 (X-2),
- in which R8 is C1-C8-alkyl.
11 more elements
Dependencies are inferred from the claim text.