Patent ID: 6410732
Filing Date: 2002-06-25
Classification: C07D

Abstract:
A process for preparing an N-arylacridancarboxylic acid derivative of the formula (1): wherein R1 is selected from alkyl, substituted alkyl, heteroalkl, aralkyl, substituted aralkyl, aryl, substituted aryl and heteroaryl groups, Z is selected from O and S atoms or the group ZR1 is an â€”NR10R11 group wherein R10 and R11 are independently selected from alkyl, substituted alkyl, aryl, substituted aryl, aralkyl, alkylsulfonyl and arylsulfonyl groups, and wherein R10 and R11 can be combined with N into a heterocycle with leaving group ability, each of R2-R9 is independently selected from substituents which contain from 1 to 50 atoms selected from C, H, N, O, S, P and halogen atoms and wherein Ar is selected from aryl, substituted aryl and heteroaryl groups, the process comprising the steps of:a) reducing an acridone compound (2) having the formula: â€ƒwherein R2-R9 are as defined above to an acridan compound (3) having the formula: â€ƒwherein R2-R9 are as defined above; b) converting the acridan compound (3) to an N-arylacridan compound (4) having the formula: â€ƒwherein R2-R9 are as defined above and Ar is an aryl, substituted aryl or heteroaryl ring group by reacting the acridan compound with an arylating compound selected from aryl, substituted aryl and heteroaryl halides and aryl, substituted aryl and heteroaryl sulfonate esters in an inert solvent in the presence of a base and a palladium catalyst; and c) converting the N-arylacridan (4) to the N-arylacridancarboxylic acid derivative by a carboxylation reaction in which a carbonyl-containing group is attached to the 9-position of the acridan ring.