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US 5,352,820 AGranted
Expedient route to aryl propenoic esters
OwnerJeremy I. Levininventor
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Abstract
The invention is an expedient route to synthesizing substituted or unsubstituted aryl-2-propenoic esters. The substituted or unsubstituted aryl-2-propenoic esters are useful in preparing optically active substituted or unsubstituted 2-arylpropanoic acids known to be active anti-inflammatory agents.
Claims40
The process for making a substituted or unsubstituted aryl-2-propenoic ester of formula I:
- ##STR9## wherein Ar is ##STR10## Z is NH, O or S;
- X and X' are independently hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkanoyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, trifluoromethyl, nitro, bromine, chlorine, fluorine, phenyl, substituted phenyl wherein the substitution is hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkanoyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, trifluoromethyl, nitro, bromine, chlorine or fluorine, thiophene, pyridine or furan;
- and R is (C.sub.1 -C.sub.4)alkyl;
- which comprises:
- reacting a substituted or unsubstituted aryl iodide of the formula:
- Ar--.vertline.
- wherein Ar is as defined hereinabove;
- with an .alpha.-stannyl acrylate ester of the formula:
- ##STR11## wherein R is as defined hereinabove and R.sup.1 is (C.sub.1 -C.sub.4)alkyl;
- in the presence of palladium(0) or palladium(II), and copper(I or II) catalyst, in a polar-aprotic solvent at room temperature for from 1 to 100 hours and recovering the substituted or unsubstituted aryl-2-propenoic ester so produced.
7 more elements
The process for making substituted or unsubstituted aryl-2-propenoic esters of formula I, ##STR12## wherein Ar is ##STR13## Z is NH, O or S;
- X and X' are independently hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkanoyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, trifluoromethyl, nitro, bromine, chlorine, fluorine, phenyl, substituted phenyl wherein the substitution is hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkanoyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, trifluoromethyl, nitro, bromine, chlorine or fluorine, thiophene, pyridine or furan;
- and R is (C.sub.1 -C.sub.4)alkyl;
- which comprises:
- reacting a substituted or unsubstituted aryl triflate of the formula;
- ##STR14## with an .alpha.-stannyl acrylate ester of the formula:
- ##STR15## wherein R is as defined hereinabove and R.sup.1 is (C.sub.1 -C.sub.4)alkyl;
- in the presence of palladium(0) or palladium(II), copper(I or II), and lithium chloride catalyst, in a polar-aprotic solvent at room temperature for from 1 to 100 hours and recovering substituted or unsubstituted aryl-2-propenoic esters so produced.
4 more elements
Dependencies are inferred from the claim text.