ICl [27]; (ii) the lithium chloride-mediated copper(I) iodide-catalyzed 1acetonitrile at reflux
ICl [27]; (ii) the lithium chloride-mediated copper(I) iodide-catalyzed 1acetonitrile at reflux) (1 equiv), dimethylformamide (DMF) at 120 C) [28]; (iii) the copperdiamine technique created by Buchwald and PSB-603 site coworkers to N-arylate (0.1 equiv), K2CO3 arylation of azaindoles reported by Yum and coworkers (System B: CuI azoles (Method C: CuI (five mol ), K(1 equiv), dimethylformamide (DMF) at 120) [28]; (iii)0.1 equiv), DMF (three equiv), LiCl three PO4 (2 equiv), N,N’-dimethylethylenediamine (DMEDA; the copper-diaat reflux) [29]; created by Buchwald and coworkers to N-arylate azoles (Process C: CuI mine strategy (iv) the protocol Teo and coworkers utilised to N-arylate azoles, including 7-azaindole, 3PO4 (2 equiv), N,N’-dimethylethylenediamine (DMEDA;(two equiv), dimethyl(5 mol ), K with iodopyridines (Approach D: Cu2 O (0.1 equiv), Cs2 CO3 0.1 equiv), DMF at sulfoxide (DMSO) at 110 C) [30]; and (v) the `ligand-free’ procedure Yum and coworkers reflux) [29]; (iv) the protocol Teo and coworkers utilised to N-arylate azoles, like 7employed to N-arylate carbazole under microwave irradiation (Process E: CuI (0.1 equiv), azaindole, with iodopyridines (System D: Cu2O (0.1 equiv), Cs2CO3 (two equiv), dimethylCs2 CO3 (1(DMSO)DMF, MWI[30]; and (v) the `ligand-free’ procedure Yum and coworkers sulfoxide equiv), at 110) at 350 W) [31]. The results are shown in Table 1. The microwave irradiation (Approach E: CuI (0.1 equiv), employed to N-arylate carbazole under reactions performed from iodobenzene (entries 1) andCO3 (1 equiv), DMF, MWI at 350 W) [31].efficiently carried out with strategies making use of a 4-iodoanisole (entries 60) had been extra Cs2 ligand (DMEDA for Process C, or DMSO for Approach D). As a result, we GNE-371 In Vivo applied them toMolecules 2021, 26, x FOR PEER Assessment Molecules 2021, 26, x FOR PEER Review Molecules 2021, 26, x FOR PEER REVIEW3 of 34 three of 34 3 ofMolecules 2021, 26,The outcomes are shown in Table 1. The reactions performed from iodobenzene (entries The results are shown in Table were reactions performed from iodobenzene (entries 1) and 4-iodoanisole (entries 60)1. Themore effectively carriediodobenzene (entries The outcomes are shown in Table 1. The reactions performed from out with approaches utilizing 3 1) and (DMEDA for Method C, or DMSO for Method D). carried out we applied of 33 to a ligand 4-iodoanisole (entries 60) were extra effectively Hence, with strategies applying them 1) and 4-iodoanisole (entries 60) have been more efficiently carried out with methods applying a ligand (DMEDA for Approach C, or DMSO for Method D). For that reason, we applied them to 1-arylate 7-azaindole with C, or DMSO for Technique D). Consequently, we applied them to a ligand (DMEDA for Method 1-chloro-4-iodobenzene (entry 11), 1-fluoro-4-iodobenzene (en1-arylate 7-azaindole with 1-chloro-4-iodobenzene 13 and 14), 1-iodo-3,5-dimethylbentry 12), 1-iodo-4-(trifluoromethyl)benzene (entries(entry 11), 1-fluoro-4-iodobenzene (en1-arylate 7-azaindole with 1-chloro-4-iodobenzene (entry 11), 1-fluoro-4-iodobenzene (entry 12), 1-iodo-4-(trifluoromethyl)benzene (entries 13 1-fluoro-4-iodobenzene (en1-arylate 1-iodo-4-(trifluoromethyl)benzene (entries 17), andand 14), 1-iodo-3,5-dimethylbentry zene (entry 15), 2-iodothiophene (entries 16 and 13 3-iodopyridine (entries 18 and 19), 212), 7-azaindole with 1-chloro-4-iodobenzene (entry 11),14), 1-iodo-3,5-dimethylbenzene (entry 15), 2-iodothiophene (entries 16 try 12), 1-iodo-4-(trifluoromethyl)benzene 16 andand 17), 3-iodopyridine (entries 18 and 19), 2bromopyridine (entries 20 and 21) and(e.
