Método para a fabricação de pirazóis substituídos por por piridil.

摘要

Producing pyridyl-substituted pyrazole compounds (I) comprises: (a) reacting acetylene ketone compounds (II) with pyridyl-hydrazine compounds (III) to obtain 1-pyridyl-substituted dihydro-1H-pyrazole compounds (IV); (b) optionally further reacting without prior isolation under the elimination of water to obtain 1-pyridyl-substituted trihalomethylpyrazole compounds (V); (c) reacting (V) under the addition of e.g. sulfuric acid to give pyrazole carboxylic acid compounds (VI); (d) deprotecting (VI) to obtain hydroxymethylpyrazolic acid compounds (VII); and converting (VII) to (I). Producing pyridyl-substituted pyrazole compounds of formula (I) comprises: (a) reacting acetylene ketone compounds of formula (X 3C-C(=O)-C?=C-CH 2-OR4) (II) with pyridyl-hydrazine compounds of formula (III) to obtain 1-pyridyl-substituted dihydro-1H-pyrazole compounds of formula (IV); (b) optionally further reacting without prior isolation under the elimination of water to obtain 1-pyridyl-substituted trihalomethylpyrazole compounds of formula (V); (c) reacting (V) under the addition of e.g. sulfuric acid to give pyrazole carboxylic acid compounds of formula (VI); (d) deprotecting (VI) to obtain hydroxymethylpyrazolic acid compounds of formula (VII); and converting (VII) to (I). R1 : alkoxy, OH, aryloxy, alkylaryloxy, alkyl, cycloalkyl, halo; R2 : OH, alkoxy, arylalkoxy, alkylthio, Cl, Br, F, I, O-(C=O)alkyl, O-(C=O)O-alkyl, OSO 2alkyl, OSO 2phenyl, OSO 2haloalkyl or OSO 2-aryl; R3 : halo, CN, NO 2, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino or cycloalkylamino; R4 : protecting group e.g. (1-6C)-alkyl, aryl, benzyl, tetrahydropyran, (C=O)-alkyl, (C=O)-Oalkyl or Si(alkyl) 3; and X : halo. Independent claims are included for: (1) 1-pyridyl-substituted dihydro-1H-pyrazole compounds (IV) (where R3 is Cl and R4 is benzyl); (2) 1-pyridyl-substituted trihalomethylpyrazole compounds (V) (where X is halo, preferably Cl, R3 is Cl and R4 is benzyl); and (3) hydroxymethylpyrazolic acid compounds (VII). [Image] [Image].