Mental-catalyzed process for preparation of substituted pyrazolecarboxamides

1. A process for preparing carboxamides of the formula (I)

in which

R 1 is hydrogen, halogen, —C(R′) 3 where R′ is hydrogen, fluorine or O—C 1-4 -alkyl;

R 2 is —CH(Me)—CH 2 —CH(Me) 2 , —CH 2 —CH 2 -t-But, or

A is formula (A1)

in which

R 3 is hydrogen, cyano, halogen, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, aminocarbonyl, aminocarbonyl-C 1 -C 4 -alkyl, or C 1 -C 4 haloalkylthio having from 1 to 5 halogen atoms;

R 4 is halogen;

R 5 is hydrogen, C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkylthio-C 1 -C 4 -alkyl wherein C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl has, in each case, from 1 to 5 halogen atoms, or phenyl;

comprising reacting a carboxamide of the formula (II)

with a haloalkylbenzene of the formula (III)

in which X is halogen

in a metal-catalyzed reaction wherein metal catalyst is selected from the group consisting of palladium and copper catalysts.

2. The process as claimed in claim 1 , wherein the carboxamide of formula (VI)

is converted to a carboxamide of the formula (VIII)

wherein

Z is methyl, and

Y is fluorine.

3. The process as claimed in any one of claims 1 and 2 , characterized in that at least one copper catalyst is used in the presence of a ligand, wherein said ligand is selected from the group consisting of N,N′-dimethyl-1,2-cyclohexanediamine, N,N′-dimethylethylenediamine, ethylenediamine, N-methylethylenediamine, N-butylethylenediamine, N,N,N′-trimethylethylenediamine, 1,10-phenanthroline, ethylenediaminetetraacetic acid, tetra-n-butylammonium fluoride, and tris(3,6-trioxaheptyl)amine (TDA-1).

4. The process as claimed in claim 3 , wherein said ligand is a diamine.

5. The process as claimed in claim 3 using a base.

6. The process as claimed in claim 4 using a base.

7. The process as claimed in any one of claims 1 and 2 using a base.