Process for preparing halogenated pyridine derivatives
US-10875858-B2 · Dec 29, 2020 · US
US11479565B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11479565-B2 |
| Application number | US-201917283270-A |
| Country | US |
| Kind code | B2 |
| Filing date | Oct 9, 2019 |
| Priority date | Oct 11, 2018 |
| Publication date | Oct 25, 2022 |
| Grant date | Oct 25, 2022 |
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The present invention relates to a process for preparing substituted imidazole derivatives of the formula (II) from compounds of the formula (I) via intermediates of the formula (IVa) or (IVb) in which the structural elements shown in the formulae (I), (II), (IVa) and (IVb) have the meanings given in the description. Furthermore, the invention relates to the intermediates of the formulae (IVa) and (IVb).
Opening claim text (preview).
The invention claimed is: 1. A process for preparing a compound of formula (II) in which Q represents a structural element where the symbol # indicates the bond to the rest of the molecule and Q 1 represents N or CR 6 , Q 2 represents N or CR 6 , Q 3 represents C, Q 4 represents O, S, N, or NR 7 , Q 5 represents C, Q 6 represents N and Q 7 represents CH, where R 6 represents hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-cyanoalkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkoxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkenyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-haloalkenyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-cyanoalkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-alkynyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkyl-(C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulfinyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulfonyl-(C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkylcarbonyl-(C 1 -C 4 )-alkyl and R 7 represents (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-cyanoalkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkoxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkenyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-haloalkenyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-cyanoalkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-alkynyloxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkyl-(C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulfinyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulfonyl-(C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkylcarbonyl-(C 1 -C 4 )-alkyl, A represents hydrogen, cyano, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-haloalkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkoxyimino, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-haloalkylsulfinyl, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 4 )-haloalkylsulfonyl, (C 1 -C 4 )-alkylsulfonyloxy, (C 1 -C 4 )-alkylcarbonyl, (C 1 -C 4 )-haloalkylcarbonyl, aminocarbonyl, (C 1 -C 4 )-alkylaminocarbonyl, di-(C 1 -C 4 )-alkylaminocarbonyl, (C 1 -C 4 )-alkylsulfonylamino, (C 1 -C 4 )-alkylamino, di-(C 1 -C 4 )-alkylamino, aminosulfonyl, (C 1 -C 4 )-alkylaminosulfonyl or di-(C 1 -C 4 )-alkylaminosulfonyl, or A represents —O—CF 2 —O— and, together with Q 1 and the carbon atom to which it is attached, forms a five-membered ring where Q 1 represents carbon, W represents halogen or S(O) n R 8 , where R 8 represents (C 1 -C 6 )-alkyl, (C 1 -C 6 )-cyanoalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl or (C 3 -C 8 )-cycloalkyl and n represents 0, 1 or 2, V represents (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-cyanoalkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkoxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkenyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-cyanoalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-alkynyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkynyloxy-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-cyanoalkynyl, (C 3 -C 8 )-cycloalkyl, (C 3 -C 8 )-cycloalkyl-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-alkyl-(C 3 -C 8 )-cycloalkyl, halo-(C 3 -C 8 )-cycloalkyl, cyano-(C 3 -C 8 )-cycloalkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylcarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl or (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-alkyl and Y represents halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-haloalkylsulfinyl, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 4 )-haloalkylsulfonyl, SCN, (C 1 -C 4 )-alkylcarbonyl, (C 1 -C 4 )-haloalkylcarbonyl, (C 1 -C 4 )-alkoxycarbonyl, (C 1 -C 4 )-haloalkoxycarbonyl, (C 1 -C 4 )-alkylaminocarbonyl, di-(C 1 -C 4 )-alkylaminocarbonyl, (C 1 -C 4 )-haloalkylaminocarbonyl, (C 3 -C 6 )-cycloalkylaminocarbonyl, (C 1 -C 4 )-alkylaminothiocarbonyl, di-(C 1 -C 4 )-alkylaminothiocarbonyl, (C 1 -C 4 )-haloalkylaminothiocarbonyl, (C 3 -C 6 )-cycloalkylaminothiocarbonyl, (C 1 -C 4 )-alkylamino, (C 1 -C 4 )-haloalkylamino, di-(C 1 -C 4 )-alkylamino, (C 3 -C 6 )-cycloalkylamino, (C 1 -C 4 )-alkylsulfonylamino, (C 1 -C 4 )-alkylcarbonylamino, (C 1 -C 4 )-haloalkylcarbonylamino, (C 1 -C 4 )-alkylcarbonyl-(C 1 -C 4 )-alkylamino, (C 1 -C 4 )-haloalkylcarbonyl-(C 1 -C 4 )-alkylamino, (C 3 -C 6 )-cycloalkylcarbonylamino, (C 3 -C 6 )-cycloalkylcarbonyl-(C 1 -C 4 )-alkylamino, (C 1 -C 4 )-alkylthiocarbonylamino, (C 1 -C 4 )-haloalkylthiocarbonylamino, (C 1 -C 4 )-alkylthiocarbonyl-(C 1 -C 4 )-alkylamino, (C 1 -C 4 )-haloalkylthiocarbonyl-(C 1 -C 4 )-alkylamino, (C 3 -C 6 )-cycloalkylthiocarbonylamino, (C 3 -C 6 )-cycloalkylthiocarbonyl-(C 1 -C 4 )-alkylamino, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-cyanoalkenyl, (C 3 -C 6 )-cycloalkyl-(C 2 )-alkenyl, (C 2 -C 4 )-alkynyl or (C 2 -C 4 )-haloalkynyl, or represents (C 3 -C 6 )-cycloalkyl or (C 5 -C 6 )-cycloalkenyl, each of which is optionally mono- or polysubstituted by identical or different substituents, possible substituents being in each case: (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, aminocarbonyl, aminothiocarbonyl, halogen or cyano, or represents aryl or hetaryl, each of which is optionally mono- or polysubstituted by identical or different substituents, where (in the case of hetaryl) optionally at least one carbonyl group may be present and where possible substituents in each case are as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxy, amino, SCN, SF 5 , tri-(C 1 -C 4 )-alkylsilyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkyl-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-haloalkyl-(C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, cyano-(C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-cyanoalkyl, (C 1 -C 4 )-hydroxyalkyl, hydroxycarbonyl-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxycarbonyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 2 -C 4 )-cyanoalkenyl, (C 3 -C 6 )-cycloalkyl-(C 2 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-haloalkynyl, (C 2 -C 4 )-cyanoalkynyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-cyanoalkoxy, (C 1 -C 4 )-alkoxycarbonyl-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkoxyimino, (C 1 -C 4 )-haloalkoxyimino, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylthio-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-haloalkylsulfinyl, (C 1 -C 4 )-a
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