Process for the preparation of pyrazole carboxylic acid amides

A process for the preparation of the compound of formula I

• which process comprises
• a) reacting a compound of formula II
• wherein X is chloro or bromo, with an organometallic species in an inert atmosphere to a halobenzyne of formula III
• wherein X is chloro or bromo;
• reacting the halobenzyne of formula III so formed with a fulvene of formula IV
• wherein R1 and R2 are independently hydrogen or C1-C6alkyl;
• to a compound of formula V
• wherein R1 and R2 are independently hydrogen or C1-C6alkyl and X is chloro or bromo;
• b) hydrogenating the compound of formula V in the presence of a suitable metal catalyst to a compound of formula VI
• wherein R1 and R2 are independently hydrogen or C1-C6alkyl and X is chloro or bromo;
• c) ozonising the compound of formula VI to a compound of formula VII
• wherein X is chloro or bromo;
• d) converting the compound of formula VII in the presence of a phosphane and CCl4 or CHCl3 to the compound of formula VIII
• wherein X is chloro or bromo;
• and either
• e1) reacting the compound of formula VIII with NH3 in the presence of a catalyst comprising palladium and at least one ligand to the compound of formula IX
• and f) reacting the compound of formula IX in the presence of a base with the compound of formula X
• to the compound of formula I;
• or
• e2) reacting the compound of formula VIII
• wherein X is chloro or bromo;
• in the presence of a solvent, a base, a copper catalyst and at least one ligand with the compound of formula Xa
• to the compound of formula I.