Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1996-07-22
1998-03-10
Davis, Zinna Northington
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
558286, 558287, 544319, C07D21353, C07C25148
Patent
active
057263434
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/00146.
The present invention relates to a novel process for the preparation of an unsubstituted or ting-substituted 2-methoxyimino-2-arylacetic ester of the formula I ##STR1## wherein one CH group of the aromatic ring group may be replaced by N forming pyridyl and wherein two of the four substitutable valencies of the ring may in adjacent position represent a fused-on, unsubstituted or substituted five- or six-membered ring which may contain one to three identical or different heteroatoms selected from N, S and O, and in which ##STR2## or of the trimeric form IlI ##STR3## which is in equilibrium with it, in the presence of a palladium catalyst, with a methoxyiminoacetic ester of the general formula IV ##STR4## in which R is C.sub.1 -C.sub.12 alkyl and X is a leaving group, or ##STR5## in which R and R.sub.8 are each C.sub.1 -C.sub.12 alkyl in the presence of a Pd catalyst, with a halophenyl compound of the general formula XI ##STR6## which is substituted as desired and in which Y is Br or I and the four valencies in the phenyl ring represent the possible substituents mentioned for the structural formula I.
The term leaving group refers to a nucleofugic radical. Examples are, for instance, halogen (e.g. chlorine, bromine or iodine) or sulfonates --O--SO.sub.2 --C.sub.6 H.sub.4 --CH.sub.3, --O--SO.sub.2 --CF.sub.3, etc.!.
Particular preference is given to compounds of the formula IV, Xa and Xb in which R.dbd.CH.sub.3.
The palladium catalyst can in principle be chosen as desired. Metallic Pd or Pd/C can be used. Preferred examples are the following compounds: Pd.sup.(II) (OAc).sub.2, (.O slashed..sub.3 P).sub.2 Pd.sup.(II) (OAc).sub.2, (.O slashed..sub.3 P).sub.2 Pd.sup.II) Cl.sub.2, (.O slashed..sub.3 P).sub.4 Pd.sup.(0), dichlorobis(triphenylstet wherein .phi. denotes phenyl. This list of Pd catalysts is not limiting.
More precisely, the invention relates to a process for the preparation of a microbicidally/insecticidally active compound of the formula Ia ##STR7## from boronic acid Ila represented by the structure ##STR8## in which R is C.sub.1 -C.sub.12 alkyl and unsubstituted or substituted cycloalkyl, unsubstituted or substituted aralkyl, unsubstituted or substituted aryloxyalkyl, unsubstituted or substituted arylthioalkyl, unsubstituted or substituted heteroarylalkyl, unsubstituted or substituted heteroaryloxyalkyl, unsubstituted or substituted heteroarylthioalkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted aralkenyl, unsubstituted or substituted aryloxyalkenyl, unsubstituted or substituted arylthioalkenyl, unsubstituted or substituted heteroarylalkenyl, unsubstituted or substituted heteroaryloxyalkenyl, unsubstituted or substituted heteroarylthioalkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted arylalkynyl, unsubstituted or substituted heteroarylalkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted arylazo, unsubstituted or substituted acylamino, --OR.sub.12, --SR.sub.13, --SOR.sub.14, --SO.sub.2 R.sub.15, --COOR.sub.16, --CONR.sub.17 R.sub.18, --COR.sub.19, --CR.sub.20 .dbd.NR.sub.21, --N.dbd.CR.sub.22 R.sub.23--, --CR.sub.24 .dbd.N--OR.sub.25, --CR.sub.25 R.sub.26 --O--N.dbd.CR.sub.27 R.sub.28, --CH.sub.2 --OCOR.sub.39 or --NR.sub.37 R.sub.38, in which the groups R.sub.12 to R.sub.28 and R.sub.38 and R.sub.39 are identical or different and are hydrogen, unsubstituted or substituted C.sub.1 -C.sub.6 alkyl, unsubstituted or substituted C.sub.1 -C.sub.6 alkenyl, unsubstituted or substituted C.sub.1 -C.sub.6 alkynyl, unsubstituted or substituted C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted cycloalkylalkyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aralkyl, unsubstituted or substituted heteroarylalkyl, unsubstituted or substituted aryloxyalkyl, unsubstituted or substituted arylthioalkyl or unsubstituted or substituted heteroarylthioalkyl and R.sub.37 is hydrogen or C.sub.1 -C.sub.4 alk
REFERENCES:
patent: 4999042 (1991-03-01), Anthony et al.
patent: 5157144 (1992-10-01), Anthony et al.
Chemical Abstracts, 55, 19839e (1961).
Chemical Abstracts, 55, 3484 b (1961).
Chemical Abstracts, 78, 58494 (1973).
Noria Miyaura et al, Tetrahedron Letters, Vol. 27, pp. 3745-3748 (1986).
M.J. Sharp et al., Tetrahedron Letters, Vol. 28, pp. 5093-5096 (1987).
Tatano Ishiyama et al., Chemistry Letters, Vol. pp. 25-28, (1987) The.
Neff Denis
Stutz Wolfgang
Ziegler Hugo
Davis Zinna Northington
McC. Roberts Edward
Morris Michael P.
Novartis Corporation
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