1-(4-Nitrophenyl)-1H-imidazole

General procedure: A 10mL round bottom flask was charged with a magnetic stirring bar, benzimidazole 1 (59mg, 0.5mmol), boronic acid 2 (1.0mmol), CuGeneral procedure: A mixture of imidazole (1 mmol), phenylboronic acid (2 mmol), K2CO3 (2 mmol), Cu(CH3COO)2H2O (1 mol percent, 1.99 mg) and L1 (1 mol percent, 5.7 mg) in ethanol (5 mL) was stirred at room temperature in a 50 mL oven dried round bottomed flask. After the completion of the reaction (as monitored by TLC), conventional workup of the reaction mixture was done with ethyl acetate (3 × 15 mL) and water (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered and the solvent was evaporated in a rotary evaporator under reduced pressure to get the crude product. The crude product was purified by column chromatography on silica gel (DCM: Methanol = 9:1) to afford the pure product.General procedure: A dry flask was charged with the nitrogen containing heterocycles (1 mmol), aryl boronic acids (2.2 mmol), potassium carbonate (2 mmol) andCuMeSal (0.015 mmol)then anhydrous methanol (10 ml) was added. The reaction mixture was stirred at 65 oC, open to air, for 3 h (5 h in case of indole and benzimidazole), cooled to room temperature, filtered, and the precipitate was washed with methanol (2 ml), the filtrate was concentrated under vacuum, then stirred with ice water (30 ml) and extracted with ethyl acetate (3 × 50 ml), dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by chromatography or recrystallization as indicated with each compound.General procedure: To a solution of 1 (0.02 mmol) in H2O/MeCN (v/v=2/1, 4 mL) was added 1H-imidazole (1.0 mmol) and arylboronic acid (2 mmol)under O2 atmosphere. The mixture was stirred at 60 °C for 24 h. After cooling to ambient temperature, the mixture was partitioned between water and CH2Cl2. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel.General procedure: In a 25 mL round bottomed flask was taken a mixture of phenol/amine/thiophenol (1.2 mmol, 0.112 g), 4-nitrochlorobenzene (1 mmol, 0.157 g), base KOH (1.2 mmol, 0.08 g) and 1 mL DMSO was added. Further 2.5 mol percent catalyst (4.5 mg) was added to the reaction mixture. The reaction mixture was heated to 110 °C for appropriate time. Reaction is monitored on TLC. After completion of the reaction the catalyst was separated by centrifugation and subsequently washed with dichloromethane. The reaction mixture was diluted with water and the product was extracted by dichoromethane (3 .x. 10 cmGeneral procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), CuGeneral procedure: In a typical experiment, imidazole (1.2 mmol), aryl halide (1.0 mmol), catalyst, and base (2.0 mmol) were added to a hydrothermal reactor (20 mL). The mixture was heated to the desired temperature with stirring. After the completion of the reaction and cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate (3 × 15mL). The combined organic extracts were dried with anhydrous Na2SO4 and the obtained product was purified by column chromatography on silica gel using dichloromethane: methanol (100:1, v/v) as the eluent.General procedure: A mixture of aryl iodide (1.0 mmol), Het-NH (1.2 mmol), KOH (2 mmol), nanomagnetic Fe(1) will p-nitrochlorobenzene 0.158g (1.0mmol), imidazole 0.069g (1.0mmol), Cu (OAc)General procedure: A mixture of p-nitro chlorobenzene 3 (25.0 g, 0.200 mol), appropriatesecondary amine 2a, b, e, f (0.300 mol) and anhydrous potassiumcarbonate (40.0 g) were mixed in DMF (300 mL), and thencatalytic drops of Aliquat 336 reagent were added. The mixturewas heated from 24 to 36 h at 100 C. The reaction mixture wasthen concentrated under vacuum, cooled and poured into ice waterand left aside overnight. The formed solid was filtered, washedwith water and crystallized from ethanol to yield titled compoundsIVa, b, e, f. 1-(4-Nitrophenyl)-1H-imidazole IVa 33.1 1-(4-nitrophenyl)-1H-imidazole: 33.1 1-(4-nitrophenyl)-1H-imidazole a a 1. Step 4 General procedure: In a 50mL RB, N−H heterocycles (1.0mmol), aryl halide (1mmol), Cu(II)Pc (0.01mmol), NaOH (1.5mmol) and DMSO (2mL) was added. This reaction mixture was stirred to a preheated oil bath at 100°C for 8–12h. After completion of the reaction, it was cooled to room temperature and 20mL ethyl acetate was added. It was filtered; solid catalyst was separated and washed with 2×5mL ethyl acetate. The washing and filtrate were combined and washed with water. Ethyl acetate was removed under reduced pressure and product was purified with column chromatography.General procedure: A mixture of CuatCu2O NPs nanocomposite (5 molpercent ofCu), Cs2CO3(1.5 mmol), N-heterocycle (1.0 mmol), aryl halide(1.0 mmol), and DMSO (2 mL) under air was stirred for 1 h at 110 °C.After completion of the reaction as indicated by TLC, the heterogeneous mixture was cooled to room temperature and diluted with ethyl acetate (10 mL). The mixture was filtered through a pad of celite. The filtrate was concentrated and then residue was purified by column chromatography (SiO2, ethyl acetate and n-hexane) to yield pure product. The catalysts were recovered by simple filtration and washed extensively with acetone and deionized water and then drying in the air.General procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), CuGeneral procedure: In an oven dried 100 mL round bottom flask, Cu-grafted catalyst(0.05 g), aryl halide (1 mmol), N–H heterocycles (1.2 mmol), K2CO3(2 mmol), and 10 mL DMSO were stirred under nitrogen atmo-sphere, at 100C. The reaction mixtures were collected at differenttime interval and identified by GC–MS and quantified by GC anal-ysis.General procedure: To a mixture of 0.05 g catalyst and aryl halide (1.0 mmol)in 9.0 cm3 DMSO, Het-NH (1.2 mmol) and K2CO3(2.0 mmol) was added and the mixture was vigorouslystirred at 120 C for the appropriate time under a drynitrogen atmosphere. After completion (as monitored byTLC), the catalyst was filtered, and the filtrate wasextracted with ethyl acetate (3 9 20 cm3) and the combinedorganic layers were dried with anhydrous MgSO4, filtered, and evaporated under reduced pressure. The residuewas purified by column chromatography. The purity ofthe compounds was checked by 1H NMR and yields arebased on aryl bromide. All the products are known and thespectroscopic data (FT-IR and NMR) and melting pointswere consistent with those reported in the literature [36–41].General procedure: A 10-mL vial was charged with aryl halide (0.5 mmol), CsGeneral procedure: A mixture of aryl iodide (1.0 mmol), Het-NH (1.2 mmol), KOH (2 mmol), nanomagnetic FeGeneral procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and KGeneral procedure: For the catalysis reaction, the catalyst C1 (12 mg, 0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 °C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.General procedure: At first [Cu(Im12)2]CuCl2 (0.5 mmol, 0.305 g) was added to a 25 mL round bottom flask containing water (4 mL), indole (0.117 g, 1 mmol) and iodobenzene (0.203 g, 1 mmol).K2CO3 (0.276 g, 2 mmol) and TBAB (0.322 g, 1 mmol) was added and the reaction stirred at 80 °C for 12 h. The reaction progress was monitored by TLC(EtOAc/n-hexane; 1:3 v/v) and after completion, the organic phase was extracted from the ionic liquid with EtOAc (2 8 mL) and concentrated in vacuo. The promoter was used directly for the next run. The product was purified by silica gel column chromatography (EtOAc/n-hexane; 1:3 v/v). The isolated product was dried under vacuum overnight to give a yield of 92percent. All products are known in the literature and were identified by comparison of their FT-IR, 1H, and 13C NMR spectra with the literature data.General procedure: A 10 mL of vial was charged with CuI (10 mg, 0.05 mmol), PSP (0.25 mmol, size less than 90 μM), TBAB (40 mg, 0.25 mmol), base (1.0 mmol), aryl halides (0.5 mmol), arylamine (2.0 mmol), H(1) will nitroiodobenzene 0.248g (1.0mmol), imidazole 0.069g (1.0mmol), Cu (OAc)General procedure: The reaction flask, containing 0.02 g Cu(II) nanocatalyst(contains 0.4 molpercent of Cu(II)), imidazole (2.0 mmol), K2CO3 (1.0 mmol), and corresponding aryl halide(1.0 mmol) in 2.5 cm3 DMF, was immersed in a preheated oil bath and the reaction mixture was stirred under air atmosphere at 120 C until no further conversion of the starting aryl halide was observed by thin-layer chromatography(TLC). After completion of the reaction, the resulting mixture was allowed to cool to room temperature, and then the catalyst was separated out by an external permanent magnet, washed with ethyl acetate (EtOAc) anddried. The residue mixture was diluted by H2O and extracted with EtOAc (3 9 10 cm3). The extracted organic phases were dried over anhydrous Na2SO4, filtrated, concentrated and, finally, purified by silica gel chromatography using petroleum ether/ethyl acetate to afford the corresponding pure N-arylimidazole.General procedure: CuI (0.05 mmol), L1 (0.1 mmol), aryl halides (1.0 mmol), imidazoles (1.5 mmol), NaOH (2 mmol), and DMSO (2 mL) were added to a 10 mL of sealed tube. The reaction mixture was reacted at 110 °C in a preheated oil bath for 12 h. The reaction mixture was cooled to r.t., diluted with 10 mL H2O, and then the mixture was extracted with ethyl acetate (3× 20 mL). The combined organic phases was washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether, 2:1 to pure ethyl acetate) to afford the target products.#10;General procedure: NH-containing heterocycle (1.4 mmol) and DMF (2.0 mL) were added to a mixture of CuCl (15.0 molpercent) and ligand 1 (20.0 molpercent) in DMF (2.0 mL), aryl iodide (1.0 mmol), NaOH (2.0 mmol). The mixture was vigorously stirred at 120 °C for 14 h under a dry nitrogen atmosphere. After completion of the reaction (as monitored by TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine and dried over MgSO4. The solution was filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography. The purity of the compounds was checked by 1H NMR and yields are based on aryl iodide. All the products are known and the spectroscopic data (FT‑IR and NMR) and melting points were consistent with those reported in the literature.General procedure: CuCl (0.04mmol), L2 (0.08mmol), aryl idione or bromide (0.5mmol), imidazole or 1H-benzo[d]imidazole (0.75mmol), NaOH (1mmol), and DMSO (1mL) was added to a 5mL tube, then sealed. The mixture was stirred at 100°C for certain time. After cooling to room temperature, the mixture was quenched with 10mL HGeneral procedure: To a mixture of 0.05 g catalyst and aryl halide (1.0 mmol)in 9.0 cm3 DMSO, Het-NH (1.2 mmol) and K2CO3(2.0 mmol) was added and the mixture was vigorouslystirred at 120 C for the appropriate time under a drynitrogen atmosphere. After completion (as monitored byTLC), the catalyst was filtered, and the filtrate wasextracted with ethyl acetate (3 9 20 cm3) and the combinedorganic layers were dried with anhydrous MgSO4, filtered, and evaporated under reduced pressure. The residuewas purified by column chromatography. The purity ofthe compounds was checked by 1H NMR and yields arebased on aryl bromide. All the products are known and thespectroscopic data (FT-IR and NMR) and melting pointswere consistent with those reported in the literature [36–41].Cu (0.05 mmol), L4 (0.1 mmol), aryl halides(0.5 mmol), imidazoles (0.75 mmol), KOH (1 mmol), TBAB (0.15 mol), and H2O(1 mL) were added to a 10 mL sealed tube. The reaction mixture was reacted at120 C in a pre-heated oil bath for 12 h. The reaction mixture was cooled to room temperature, diluted with 10 mL H2O, and then the mixture was extracted with ethyl acetate (3 20 mL). The combined organic phases were washed withwater and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel (ethyl acetate/petroleum ether, 2:1 to pure ethyl acetate) to afford the target products.General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 Mpercent) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.General procedure: A mixture of aryl halide (2.4 mmol) and Cs2CO3(4.0 mmol, 0.650 g), nitrogen-containing heterocycle (2.0 mmol), dry DMF(3 mL) solvent and catalyst was stirred at 100C in an oil bath under air. After cooling to room temperature, catalyst was first separated out by centrifugation and the liquid part was extracted with water and diethylether (2 × 15 mL). The organic layers thus collected were combined and washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified bycolumn chromatography on silica gel (mesh 60–120) using an n-hexane/ethylacetate mixture as the eluent to collect the desiredproduct. The product was analyzed by 1H and13C NMR and mass spectroscopy.General procedure: A dry flask was charged with the nitrogen containing heterocycles (1.5 mmol), aryl halides (1 mmol), potassium carbonate(2 mmol) and CuMeSal (0.01 mmol)General procedure: A mixture of CuatCu2O NPs nanocomposite (5 molpercent ofCu), Cs2CO3(1.5 mmol), N-heterocycle (1.0 mmol), aryl halide(1.0 mmol), and DMSO (2 mL) under air was stirred for 1 h at 110 °C.After completion of the reaction as indicated by TLC, the heterogeneous mixture was cooled to room temperature and diluted with ethyl acetate (10 mL). The mixture was filtered through a pad of celite. The filtrate was concentrated and then residue was purified by column chromatography (SiO2, ethyl acetate and n-hexane) to yield pure product. The catalysts were recovered by simple filtration and washed extensively with acetone and deionized water and then drying in the air.General procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), CuGeneral procedure: A mixture of aryl iodide (1.0 mmol), Het-NH (1.2 mmol), KOH (2 mmol), nanomagnetic FeGeneral procedure: For the catalysis reaction, the catalyst C1 (12 mg, 0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 °C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and KGeneral procedure: A 10-mL vial was charged with aryl halide (0.5 mmol), CsGeneral procedure: The reaction flask, containing 0.02 g Cu(II) nanocatalyst(contains 0.4 molpercent of Cu(II)), imidazole (2.0 mmol), K2CO3 (1.0 mmol), and corresponding aryl halide(1.0 mmol) in 2.5 cm3 DMF, was immersed in a preheated oil bath and the reaction mixture was stirred under air atmosphere at 120 C until no further conversion of the starting aryl halide was observed by thin-layer chromatography(TLC). After completion of the reaction, the resulting mixture was allowed to cool to room temperature, and then the catalyst was separated out by an external permanent magnet, washed with ethyl acetate (EtOAc) anddried. The residue mixture was diluted by H2O and extracted with EtOAc (3 9 10 cm3). The extracted organic phases were dried over anhydrous Na2SO4, filtrated, concentrated and, finally, purified by silica gel chromatography using petroleum ether/ethyl acetate to afford the corresponding pure N-arylimidazole.General procedure: In an oven dried 100 mL round bottom flask, Cu-grafted catalyst(0.05 g), aryl halide (1 mmol), N–H heterocycles (1.2 mmol), K2CO3(2 mmol), and 10 mL DMSO were stirred under nitrogen atmo-sphere, at 100C. The reaction mixtures were collected at differenttime interval and identified by GC–MS and quantified by GC anal-ysis.General procedure: Iodobenzene (1.0 mmol), imidazole (1.5 mmol), TEPA (2.0 mmol), TBAB (0.3 mmol), CuI (0.1 mmol), and 3 mL HGeneral procedure: A mixture of the appropriate N‑nucleophile (2 mmol), 4‑bromonitrobenzene(2 mmol), t‑ButOK or KOH (in the case of 1g, 1h)(2.2 mmol) in dimethyl sulfoxide (2.5 mL) was stirred at 60 °C for 5 h(8 h in the case of 1b). After cooling and addition of water (60 mL), either a solid precipitated which was filtered, washed with water andrecrystallised from an appropriate solvent to give the product, or asuspension was generated which was extracted with ethyl acetate(3 × 30 mL), dried over Na2SO4, concentrated under reduced pressureand recrystallised from an appropriate solvent to give the desiredproductGeneral procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 Mpercent) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.

Molecular Weight:189.17
XLogP3:1.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:189.053826475
Monoisotopic Mass:189.053826475
Topological Polar Surface Area:63.6
Heavy Atom Count:14
Complexity:209
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes