Synthesis of 2‐amino‐3‐benzoylphenylacetic acid

Abstract

2‐Amino‐3‐benzoylphenylacetic acid, sodium salt was prepared from indoline through a process applicable to large scale production.

Development of a 18F‐labeled Diaryl‐Substituted Dihydropyrrolo[3,2,1‐hi]indole as Potential Probe for Functional Imaging of Cyclooxygenase‐2 with PET

“…The synthesis of indole precursor 6 a required an additional oxidation step transforming the indoline to the indole. For this, we adopted a synthesis described by Lo et al . and oxidized 1 a with manganese(IV) oxide which provided the indole 4 a in 94 % yield.…”

Diaryl-Substituted (Dihydro)pyrrolo[3,2,1-hi]indoles, a Class of Potent COX-2 Inhibitors with Tricyclic Core Structure

“…The synthetic route starting from para-substituted benzonitriles 2a – e is outlined in Scheme . The first step in this sequence is the selective benzoylation of indoline in 7-position that was achieved starting from the benzonitriles 2a – e by a BCl 3 -mediated Friedel–Crafts reaction . The reaction with the fluoro-, chloro-, methyl-, or unsubstituted nitriles ( 2b – e ) afforded the desired 7-benzoylindolines 3b – e in 78–98% yield and high purity according to TLC, HPLC, and NMR analysis.…”

“…General Procedure A for the Synthesis of 7-Benzoyl-1H-indolines (3a−e). The synthesis followed the procedure described by Lo et al 26 and Walsh et al 61 Under nitrogen atmosphere, to a solution of a 1 M BCl 3 solution in toluene (4.4 mL. 4.4 mmol) were added, in this order, indoline (449 μL, 4 mmol) in 1.8 mL of toluene, the appropriate nitrile (as given below), and anhydrous AlCl 3 (608 mg, 4.4 mmol).…”

“…The first step in this sequence is the selective benzoylation of indoline in 7-position that was achieved starting from the benzonitriles 2a−e by a BCl 3mediated Friedel−Crafts reaction. 26 The reaction with the fluoro-, chloro-, methyl-, or unsubstituted nitriles (2b−e) afforded the desired 7-benzoylindolines 3b−e in 78−98% yield and high purity according to TLC, HPLC, and NMR analysis. In contrast, the reaction of indoline with the methylsulfonylsubstituted benzonitrile 2a under the same conditions gave the 7-[4-(methylsulfonyl)benzoyl]-1H-indoline (3a) not in a pure form and 1 H NMR analysis indicated the presence of 11−35% (m/m) 2a in the mixture.…”

1-(4-Fluorobenzoyl)-9H-carbazole

“…In analogy to a procedure described by Lo et al [14], 1 was successfully synthesized by BCl 3 -mediated Friedel-Crafts acylation, starting from 9H-carbazole and 4-fluorobenzonitrile (Scheme 1). The reaction mechanism is suggested to follow the mechanism known in the literature, which involves (1) the formation of 9-(dichloroboryl)-9H-carbazole and, subsequently, a six-membered complex with the nitrile group of 4-fluorobenzonitrile; (2) the Friedel-Crafts reaction, which leads to 1-aroylation due to the spatial proximity; (3) hydrolysis of the ketimine with HCl [15].…”