Process for producing herbicidal pyridazinone compounds
The present invention provides, inter alia, a process for producing a compound of Formula (I): wherein A 1 , R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined herein. The present invention further provides intermediate compounds utilised in said process, and methods for producing said intermediate compounds.
1. A process for producing a compound of Formula (I):
wherein
R 1 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 3 alkoxyC 1 -C 3 alkyl-, C 1 -C 3 alkoxyC 2 -C 3 alkoxyC 1 -C 3 alkyl-, aryl and a 5 or 6-membered heteroaryl, wherein the heteroaryl contains one to three heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein the aryl and heteroaryl component may be optionally substituted;
R 2 is C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl;
A 1 is selected from the group consisting of O, C(O) and (CR 7 R 8 ); and
R 4 , R 6 , R 7 and R 8 are each independently selected from the group consisting of hydrogen and C 1 -C 4 alkyl;
R 3 and R 5 are each independently selected from the group consisting of hydrogen and C 1 -C 4 alkyl or together may form a C 1 -C 3 alkylene chain;
the process comprising reacting a compound of Formula(II)
wherein X is a halogen;
with a compound of Formula (III)
wherein A 1 and R 3 , R 4 , R 5 and R 6 are as defined with regard to Formula (I) above;
in a reaction medium comprising:
(i) a palladium catalyst;
(ii) a suitable phosphine ligand or phosphine ligand salt;
(iii) a suitable base; and
(iv) carbon monoxide;
to give a compound of Formula (I).
2. A process according to claim 1 , wherein R 1 is an optionally substituted heteroaryl.
3. A process according to claim 1 , wherein R 1 is an optionally substituted phenyl.
4. A process according to claim 3 , wherein R 1 is phenyl optionally substituted by one or more substituents selected from the group consisting of halo, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxy, cyano and nitro.
5. A process according to claim 4 , wherein R 1 is 3,4-dimethoxyphenyl.
6. A process according to claim 1 , wherein R 2 is methyl.
7. A process according to claim 1 , wherein X is selected from the group consisting of Br, Cl and I.
8. A process according to claim 1 , wherein X is Br.
9. A process according to claim 1 , wherein A 1 is CR 7 R 8 and R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are hydrogen.
10. A process according to claim 1 , wherein the reaction medium further comprises (v) a solvent.
11. A process according to claim 10 , wherein the solvent is acetonitrile.
12. A compound of Formula (Ila1a)
13. A process for producing a compound of Formula (IIa1a), comprising reacting a compound of Formula (X)
wherein R 9 is selected from the group consisting of Cl, Br and I;
with a compound of Formula (XI)
14. A process according to claim 13 , wherein Compound (X) and Compound (XI) are reacted using a photochemical catalysed procedure.
15. A compound of Formula (X)
wherein R 9 is selected from the group consisting of Cl, Br and I.