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US 2014/0005388 A1Published application
Method for producing n-sulfonyl-substituted oxindoles
AssigneeBayer Intellectual Property GmbH
InventorsGunter Karig, Mark James Ford, Konrad Siegel, Stefan Schnatterer
Life of this patent
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Abstract
Process for the selective N-sulfonylation of oxindoles, in particular process for the N-sulfonylation of 3-triazinyloxindoles, and also N-sulfonyl-substituted 3-triazinyloxindoles and the use of N-sulfonyl-substituted oxindoles and of N-sulfonyl-substituted 3-triazinyloxindoles as intermediates for the synthesis of fine chemicals and of active ingredients in the field of pharmacy and agriculture, and also the use of these compounds as active ingredients in the field of agriculture.
Claims18
A process for preparing an N-sulfonyl-substituted oxindole of formula (3) which comprises a 6-ring heteroaryl substituent (Q) in the 3 position,
- in which
- R1a to R1d, independently of one another, are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, and also from
- (C1-C6)-alkyl, where the alkyl radical is branched or unbranched and is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl,
- (C3-C7)-cycloalkyl, where the cycloalkyl radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C3-C7)-cycloalkyl or (C1-C4)-alkoxy,
- (C1-C6)-alkoxy, where the alkoxy radical is branched or unbranched and is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl,
- (C3-C7)-cycloalkoxy, where the cycloalkoxy radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C1-C4)-alkoxy,
- (C1-C6)-alkylthio, where the alkylthio radical is branched or unbranched and is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C1-C4)-alkoxy,
- (C3-C7)-cycloalkylthio, where the cycloalkylthio radical is unsubstituted or is substituted by at least one substituents selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C1-C4)-alkoxy, and phenyl or 1-naphthyl or 2-naphthyl or a five- or six-membered heteroaromatic ring comprising from 1 to 2 heteroatoms, where said heteroatoms are selected, independently of one another, from the group consisting of O or N and where the aryl or heteroaryl radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, bromine, iodine, (C1-C4)-alkyl, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl or (C1-C4)-alkylthio, and
- R2 is
- (C1-C6)-alkyl, where the alkyl radical is unsubstituted or is completely or partially substituted with fluorine, or
- (C3-C7)-cycloalkyl, where the cycloalkyl radical is unsubstituted or is completely or partially substituted with fluorine,
- R3 is
- hydrogen or
- (C1-C6)-alkyl, where the alkyl radical is branched or unbranched and is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl,
- (C1-C6)-alkylthio, where the alkylthio radical is unsubstituted or is substituted by at least one substituents selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C1-C4)-alkoxy,
- and
- Q is
- a six-membered heteroaromatic ring comprising from 1 to 3 nitrogen atoms, where the heteroaromatic ring is unsubstituted or is substituted by at least one substituent selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl or (C3-C7)-cycloalkoxy or (C1-C4)-alkylthio,
- said process comprising reacting an oxindole compound of formula (1)
- in which
- R1a to R1d, and R3 and Q are as defined in formula (3),
- in a solvent with a sulfonyl compound (2)
- in which
- R2 is as defined in formula (3), and
- X, as leaving group, is
- fluorine, chlorine, bromine, 1-imidazolyl, 1H-benzotriazolyloxy, 1H-benzotriazolyl or
- O—SO2-R7, where R7 is defined as R2 and R2 and R7 are identical or different, or N(R8)SO2R9, where R8 is carbonyl and R9 is unsubstituted or substituted phenyl, and R8 and R9 are bonded with one another or are not bonded,
- where said reaction is carried out in the presence of
- an imidazole base substituted in the 1 position, or
- a base mixture which comprises at least one imidazole base substituted in the 1 position.
27 more elements
An N-sulfonyl-substituted 3-triazinyloxindole of formula (3-1)
- And/or a salt thereof (3-1a)
- in which, in each case,
- R1a to R1d, independently of one another, are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, and also of
- (C1-C6)-alkyl, where the alkyl radical is branched or unbranched and is unsubstituted or is substituted by at least one or more substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl,
- (C3-C7)-cycloalkyl, where the cycloalkyl radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C3-C7)-cycloalkyl or (C1-C4)-alkoxy,
- (C1-C6)-alkoxy, where the alkoxy radical is branched or unbranched and is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl,
- (C3-C7)-cycloalkoxy, where the cycloalkoxy radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C1-C4)-alkoxy,
- (C1-C6)-alkylthio, where the alkylthio radical is branched or unbranched and is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C1-C4)-alkoxy,
- (C3-C7)-cycloalkylthio, where the cycloalkylthio radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C1-C4)-alkoxy, and
- phenyl or 1-naphthyl or 2-naphthyl or a five- or six-membered heteroaromatic ring comprising from 1 to 2 heteroatoms, where said heteroatoms, independently of one another, are selected from the group consisting of O or N, and where the aryl or heteroaryl radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, bromine, iodine, (C1-C4)-alkyl, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl or (C1-C4)-alkylthio, and
- R2 is
- methyl, where the methyl is completely or partially substituted with fluorine, or (C3-C7)-cycloalkyl, where the cycloalkyl radical is completely or partially substituted with fluorine,
- R3 is
- hydrogen, or
- (C1-C6)-alkyl, where the alkyl radical is branched or unbranched and is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl,
- (C1-C6)-alkylthio, where the alkylthio radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkyl or (C1-C4)-alkoxy,
- R4 and R5, independently of one another, are in each case
- hydrogen,
- (C1-C6)-alkyl, where the alkyl radical is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl,
- (C1-C6)-alkoxy, where the alkoxy radical is branched or unbranched and is unsubstituted or is substituted by at least one substituent selected from the group consisting of fluorine, chlorine, (C1-C4)-alkoxy or (C3-C7)-cycloalkyl,
- where, in the salt of formula (3-1a), M is Li, Na, K, Cs, Ba, Mg, Ca, Zn or N(Rc)4, where Rc═H or C1-C6 alkyl, and where the number of counterions M+ is determined by a particular charge, such that an overall neutral compound of the formula (3-1a) is formed.
18 more elements
Dependencies are inferred from the claim text.