Patent ID: 6175011
Filing Date: 2001-01-16
Classification: B01J,C07D

Abstract:
The process for the preparation of an amide of the formula: ##STR6##wherein:A.sup.1 is nitrogen or CR.sup.1,A.sup.2 is nitrogen or CR.sup.2,A.sup.3 is nitrogen or CR.sup.3,A.sup.4 is nitrogen or CR.sup.4, andA.sup.5 is nitrogen or CR.sup.5,with the proviso that 1 to 3 of the ring members A.sup.1 to A.sup.5 is nitrogen and that two nitrogen atoms are not bonded directly to one another,one of the substituents R.sup.1 to R.sup.5, on a carbon atom adjacent to a ring nitrogen atom is a group of the formula --OR, in which R is an optionally substituted aromatic or heteroaromatic radical, the remaining of R.sup.1 to R.sup.5, if present, independent of one another are hydrogen. C.sub.1-4 -alkyl or aryl,R.sup.6 is hydrogen or C.sub.1-4 alkyl, andR.sup.7 is an optionally substituted aromatic or heteroaromatic radical,comprising, in a first step, reacting a dihalide of the formula: ##STR7##wherein A.sup.1 to A.sup.5 are as defined above, X is chlorine, bromine or iodine, one of the radicals R.sup.1 to R.sup.5, on a carbon atom adjacent to a ring nitrogen atom, is Z, Z is chlorine, bromine or iodine, and the remaining of radicals R.sup.1 to R.sup.5, if present, are as defined above, with an aromatic or heteroaromatic hydroxyl compound of the formula:R--OH VIwherein R is as defined above, to give a (hetero) aryloxy halogen compound of the formula: ##STR8##wherein A.sup.1 to A.sup.5, R and X are as defined above, one of the radicals R.sup.1 to R.sup.5, on a carbon atom adjacent to a ring nitrogen atom, is RO, and the remaining of radicals R.sup.1 to R.sup.5, if present, are as defined above, and, in a second step, reacting the (hetero)aryloxy halogen compound of formula (III) with carbon monoxide and a primary or secondary amine of the formula:R.sup.6 --NH--R.sup.7 IIIwherein R.sup.6 and R.sup.7 are as defined above, in the presence of a complex of palladium with a diphosphine of the formula: ##STR9##wherein,R.sup.8 is hydrogen or C.sub.1-4 -alkyl,R.sup.9 to R.sup.12 independently of one another are secondary or tertiary C.sub.3-6 -alkylC.sub.5-7 -cycloalkyl or optionally substituted phenyl,Y is CH.sub.o, NH.sub.p or oxygen,n is 0 or 1,o is 1 or 2,p is 0 or 1, andQ is a bridging alkylene or a ferrocene radical which, together with the two adjacent carbon atoms and, if present, with Y forms an optionally substituted five-membered or six-membered saturated or aromatic carbocyclic or heterocyclic ring which, as an aromatic ring, can optionally be complexed with a transition metal, and with a base other than said primary or secondary amine.