1-(4-Nitrophenyl)-1H-pyrazole

General procedure: In 50 mL round bottom flask, aryl halide (1.0 mmol), pyrazole (1.2 mmol), ligand (0.04 mmol), Cu2O (0.10 mmol), cesium carbonate (2.0 mmol), and dry solvent (20 mL) were placed under nitrogen atmosphere. The reaction mixture was heated in oil bath up to specified temperature under constant stirring for 20 h and then allowed to cool to room temperature. The reaction mixture was filtered through a plug of Celite in a fritted filter funnel and washed with ethyl acetate. If DMSO is used as solvent, it is extracted by washing the filtrate with 25 mL water for three times. The organic phase was dried over anhydrous MgSO4 and was removed under reduced pressure to provide the crude product which was purified by column chromatography on silica gel, using hexane and ethyl acetate in 3:1 ratio, respectively, as an eluent.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 92%. 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: General coupling procedure: In 50 mL round bottom flask equipped with a septum and magnetic stirrer bar, aryl halide (1.0 mmol), Amine (1.2 mmol), ligand (0.1 mmol), CuI(0.10 mmol), K2CO3 (2.0 mmol), and solvent (10 volume) .The mixture was stirred at 120 C and checked by TLC until the starting material was finished (about 16-24 h). The reaction was cooled down to room temperature, quenched with water (5 mL), and then extracted with EtOAc (10 mL). The crude solution was dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by column chromatography to afford the desired product.General procedure: Amine (1.0mmol) was added to a suspension of aryl halide(1.0mmol), K2CO3(2.0mmol), and Cu catalyst (0.047g, 7mol%) in DMSO (3.0mL) in a 10mL reaction flask. Thereaction mixture was stirred at 130C and monitored by TLC to determine completion of the reaction. Subsequently, the catalyst was separated magnetically and the reactionmixture was diluted with ethyl acetate (20mL). The solventwas evaporated under reduced pressure to get the crudeproduct and the product was purified by column chromatographyon silica using n-hexane and ethyl acetate.General procedure: Cu(OAc)2 (0.03mmol), L2 (0.06mmol), aryl idione or bromide (0.5mmol), 1H-pyrazole (0.75mmol), NaOH (1mmol), and 1, 4-dioxane (1mL) was added into a 5mL tube, then sealed. The mixture was stirred at 100C for certain time. After cooling to room temperature, the mixture was quenched with 10mL H2O and extracted with EtOAc (3×20mL). The combined EtOAc extracts were dried with anhydrous Na2SO4 and filtrated and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE/EtOAc, as the eluent, to afford the desired products.To the three-necked flask, CuI (19 mg, 0.1 mmol, 10 mol%), 1, 10-phenanthroline N, N'-dioxide (39 mg, 0.2 mmol, 20 mol%), Cs2CO3 (650 mg, 2.0 mmol). The reaction flask was evacuated under argon. To the p-nitroiodobenzene (249 mg, 1.0 mmol) was added pyrazole (102 mg, 1.5 mmol) and DMF (2 ml) under argon atmosphere. Reacted at room temperature for 18 hours until starting material is fully reacted (TLC detection reaction is complete). After completion of the reaction, a brown oil was obtained which was diluted with ethyl acetate. The inorganic salt was removed by filtration and the solvent was removed by rotary evaporation. The residue was eluted with petroleum ether / ethyl acetate Was purified by silica gel column chromatography to give 1-(4-nitrophenyl)pyrazole as a pale yellow oil. The yield was 82%.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: Complex 2 (0.05 mmol) was added to a 5 mL of a sealed tube containing the aryl iodide or bromide (0.5 mmol), 1H-pyrazole (0.75 mmol), NaOH (1 mmol), and DMSO (1 mL). The mixture was stirred at 100 C for 12 h. After being cooled to room temperature, the mixture was quenched with 10 mL H2O and extracted with EtOAc(3 × 20 mL). The combined EtOAc extracts were dried with anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure.The residue was purified by flash column chromatography on silicagel with PE/EtOAc (from 10:1 to 5:1) as the eluent to afford the pure products. All N-aryl pyrazoles reported here are known products and were characterised by 1H NMR, and GC-MS.(1) will nitroiodobenzene 0.248g (1.0mmol), pyrazole 0.069g (1.0mmol), Cu (OAc)2·H2O 0.030g (0.15mmol), 2, 2- biimidazole 0.022g (0.15mmol), NaOH 0.08g (2mmol), DMSO (2mL) was added the reaction tube with a piston, it was heated to 80 deg.] C the reaction was stirred for 48 hours .(2) TLC until the reaction was complete the reaction was followed ends.After the reaction was cooled to room temperature, diluted with water, extracted with ethyl acetate 3-4 was added, and the combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product.After the end of (3) to obtain the crude product was purified by column chromatography (petroleum ether / ethyl acetate elution) to give the desired product 7 (68% yield).General procedure: In a 50 mL round-bottom flask, pyrrole or pyrazole or indole(2.0 mM), 4-iodonitrobenzene (4.4 mM, 1.2 equiv.), Pd(PPh3)4 (2.5mol%) and K2CO3(2.2 equiv.) were added under continuous stirring condition. To this, 5.0 mL of dry DMA was then added under reflux condition at 110 C for 20 h. After completion of the reaction (monitored by thin-layer chromatography), the reaction mixture was allowed to cool at room temperature and diluted with distilled water. After that the solution was extracted with ethyl acetate and the organic layer was dried over anhydrous MgSO4, which was subjected to column chromatography to obtain the corresponding products.

Molecular Weight:189.17
XLogP3:2
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