[Cl:1][C:2]1[C:7](I)=[CH:6][C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]#[N:16])[N:11]([CH3:17])[N:10]=2)=[C:4]([F:18])[CH:3]=1.[CH3:19][OH:20].[C]=[O:22].C(N([CH2:28][CH3:29])CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:19]([O:22][CH2:28][CH3:29])=[O:20])=[CH:6][C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]#[N:16])[N:11]([CH3:17])[N:10]=2)=[C:4]([F:18])[CH:3]=15.2 g of 3-(4-chloro-2-fluoro-5-iodophenyl)-4-methyl-5-cyano-1-methyl-[1H]-pyrazole (Example H8), 60 ml of methanol, 2.8 g of triethylamine and 0.4 g of bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2) are placed into a 100 ml pressurized container and stirred for 16 hours at a temperature of 100° C. and a carbon monoxide pressure of 10 megapascal (Mpa). The solvent is subsequently evaporated and the crude product which remains is purified over a silica gel column (eluent: ethyl acetate/hexane 1/5). This gives 3.1 g (69.3% of theory) of the desired product.
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