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US 10,766,909 B2Granted
Process for preparing halogenated pyridine derivatives
AssigneeBayer CropScience AG
InventorsMarc Mosrin, Ruediger Fischer, Dominik Hager, Laura Hoffmeister, Nina Kausch-Busies, David Wilcke, Matthieu Willot
Life of this patent
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Abstract
The present invention relates to a process for preparing halogenated pyridine derivatives of the formula (II) proceeding from compounds of the formula (I) via intermediates of the formula (IIIa) or (IIIb) where the radicals Q and W are each independently halogen, R2 is halogen or —O-pivaloyl, and Y is halogen, CO2R1 or NO2, where R1 is (C1-C6)-alkyl or (C1-C6)-haloalkyl.
Claims19
A process for preparing a compound of formula (II)
- wherein
- Q and W are each independently halogen, and
- Y is halogen, CO2R1 or NO2, where R1 is (C1-C6)-alkyl or (C1-C6)-haloalkyl,
- wherein, in a first process step a), a compound of formula (I)
- wherein W and Y each have the definitions given above,
- is reacted with an organozinc base of structure (NR3R4)—Zn—R2 or (NR3R4)2—Zn wherein
- R2 is halogen or O-pivaloyl and
- R3 and R4 together form a —(CH2)4—, —(CH2)5— or —(CH2)2O(CH2)2— group, where each of these groups may optionally be substituted by 1, 2, 3 or 4 R5 radicals and R5 is selected from the group consisting of methyl, ethyl, n-propyl and i-propyl,
- to give a compound of formula (IIIa) or formula (IIIb)
- wherein W, Y and R2 each have the definitions given above,
- wherein the step a) is conducted at a temperature between 30° C. and 80° C.,
- and this compound of formula (IIIa) or (IIIb) is reacted in a second process step b) with a compound of the structure Q-X wherein X is halogen and Q has the abovementioned definition to give the compound of formula (II).
9 more elements
A compound of formula (IIIa)
- wherein
- W is fluorine,
- Y is halogen, C(O)2R1 or N(O)2, where R1 is (C1-C6)-alkyl or (C1-C6)-haloalkyl, and
- R2 is halogen or O-pivaloyl.
1 more element
A compound of formula (IIIb)
- wherein
- W is fluorine, and
- Y is halogen, CO2R1 or NO2, where R1 is (C1-C6)-alkyl or (C1-C6)-haloalkyl.
A compound of formula (II)
- wherein
- Q is iodine,
- W is fluorine, and
- Y is Br, C(O)2R1 or N(O)2, where R1 is (C1-C6)-alkyl or (C1-C6)-haloalkyl.
1 more element
Dependencies are inferred from the claim text.