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Product Details of [ 1137-68-4 ]

CAS No. :1137-68-4 MDL No. :MFCD00005586
Formula : C12H9N3 Boiling Point : -
Linear Structure Formula :- InChI Key :YNFBMDWHEHETJW-UHFFFAOYSA-N
M.W : 195.22 Pubchem ID :70821
Synonyms :
Chemical Name :2-(2-Pyridyl)benzimidazole

Calculated chemistry of [ 1137-68-4 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.32
TPSA : 41.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 2.62
Log Po/w (MLOGP) : 1.66
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.173 mg/ml ; 0.000884 mol/l
Class : Soluble
Log S (Ali) : -2.61
Solubility : 0.475 mg/ml ; 0.00243 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.06
Solubility : 0.0017 mg/ml ; 0.00000873 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 1137-68-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1137-68-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1137-68-4 ]

[ 1137-68-4 ] Synthesis Path-Downstream   1~40

  • 1
  • [ 1121-60-4 ]
  • [ 95-54-5 ]
  • [ 1137-68-4 ]
YieldReaction ConditionsOperation in experiment
99% With Ag2CO3/celite; In ethanol; at 70℃; for 3h; General procedure: To a mixture of 1,2-phenylenediamines (1.0 mmol) andaldehydes (1.1 mmol) in ethanol, 25 mol % of Ag2CO3/Celite (3 mL) was added. The resulting mixture was stirredat 70 C for 3 h. After this time, the reaction mixture wasdiluted with ethanol (50 mL) and the catalyst was separatedby filtration. Water was then added to the organic layer, andthe products were filtered and washed with water. All of theproducts are known compounds and characterized easily bycomparison with melting point, IR, [1-6] H NMR spectraldata reported in literature.
95% With 1,1'-disulfo-[2,2'-bipyridine]-1,1'-diium chloride; In ethanol; at 20℃; for 0.166667h; General procedure: A mixture of the aldehyde, oxime and/or semicarbazone, 1,2-phenylene diamines (1 mmol) and [BiPy](HSO3)2Cl2 (10 mg) in EtOH (3 ml) was stirred at room temperature. After completion of the reaction, monitored by TLC (EtOAc: n-hexane 1:1), the solvent was evaporated and H2O (3 ml) was added and the catalyst was separated. In continue, the resulting solid product was recrystallized from ethanol to obtain pure product in good to high yields.
94% With Poly[styrene-co-1-((4-vinylphenyl)methyl)pyridinium chloroaluminate]; In ethanol; at 20℃; for 0.183333h; General procedure: To a solution of aldehyde (1 mmol) and o-phenylenediamine (1 mmol) in ethanol (5 mL)was added PS-PyCl-xAlCl3 (0.1 mmol), and the resulting mixture was magnetically stirred atroom temperature. The progress of the reaction was monitored by TLC. After completion ofthe reaction, the catalyst was filtered off and washed with EtOH (2×5 mL) and the filtrate wasconcentrated on a rotary evaporator under reduced pressure to afford the crude product.Whenever required, the products were purified by column chromatography on silica gel(n-hexane/EtOAc) or recrystallization from ethanol. The spent catalyst from different experiments was washed with EtOH and reused without further drying. The analytical and spectraldata of the obtained compounds are given in the Supplementary material to this paper.
94% In ethanol; at 20℃; for 4h; Pyridine formaldehyde (2.14 g, 20 mmol) was slowly added dropwise to a solution of o-phenylenediamine (1.08 g, 10 mmol) in ethanol , The reaction at room temperature for 4 hours, after drying the solvent after a large number of light yellow solid, respectively, with 5mL n-hexane washing twice,And then recrystallized from absolute ethanol to give 2- (2-pyridyl) benzimidazole ligand in 94% yield
93% In water; N,N-dimethyl-formamide; at 80℃; General procedure: An ortho-phenylenediamine derivative 3 (1.0 mmol; 1.0 equiv) and an aldehyde 4 (1.0 mmol; 1.0 equiv) were dissolved in wet DMF (DMF 9.0 mL, H2O 1.0 mL). The resulting reaction mixture was stirred at 80C in an open flask, and the reaction progress was monitored by TLC. On the complete consumption of 3, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The crude product obtained was purified by column chromatography on silica gel to afford the corresponding benzimidazole 5.
92% With sodium dithionate; In N,N-dimethyl-formamide; for 3h;Reflux; General procedure: Equimolar mixture of pyridine carboxaldehyde deriva-tives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by the addi-tion of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice, precipitates were formed which were collected by filtration to afford compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals.
91% With graphene oxide; In water; at 60℃; for 0.75h;Green chemistry; General procedure: A mixture of aldehyde (1mmol) and o-phenylenediamine 1a (1mmol, 108.1 mg) in water (1 mL) were added to dispersed solution of GO (100 wt%, 108.7 mg) in water (2 mL) and the reaction mixture was stirred at 60 C forappropriate time (Table 2). After completion of the reaction(monitored by TLC using n-hexane/EtOAc 9:1 as eluent), theGO was separated by filtration and the solution was extractedwith ethyl acetate (2 5 mL). The GO was washed with warmethanol (about 75 C, 5 10 mL) and then organic layers(EtOAc and ethanol) were combined and dried over anhydroussodium sulfate. The solvents were removed under reducedpressure and the residue left out was purified by chromatographyon a short column of silica gel eluted with n-hexane/ethyl acetate (9:1) to give the corresponding benzimidazoles 2in 78-95%yield (Table 2).
91% With bismuth (III) nitrate pentahydrate; In water; at 80℃; for 0.333333h;Microwave irradiation; Green chemistry; General procedure: The substrate (o-phenylenediamine, 1.0 mmol), aldehyde(1.1 mmol) and bismuth nitrate pentahydrate (24 mg, 5 mol%) were mixed together with water (1mL) in a microwave vial fitted with a magnetic stir bar.The mixture was irradiated in an automated microwave(CEM Corporation, Discover model) and the progressof the reaction was monitored by TLC. After completionof the reaction (Table 4) ethyl acetate (10 mL) wasadded to the reaction mixture and the organic layer waswashed with saturated sodium bicarbonate solution,brine and water successively. It was dried over anhydroussodium sulfate and the solvent was removed underreduced pressure. The crude mass was purifiedthrough a small silica gel column using ethyl acetate/hexanes as eluent.
90% In neat (no solvent); for 0.5h;Irradiation; General procedure: In a typical experiment,a mixture of aromatic aldehyde 2 (1mmol) and o-phenylenediamine (1) (1 mmol) was taken in a test tube.The reaction mixture was stirred on magnetic stirrer in concentrated solar radiation (CSR) for 20-30 minutes and monitored by TLC. On completion of the reaction, the reaction mixture was cooled to room temperature.The 2-aryl-1H-benzimidazoles 3 were isolated by using column chromatography over Silica gel using hexane-EtOAc as eluent as and when required.
90% With oxygen; In ethanol; at 60℃; for 4h;Green chemistry; General procedure: In a typical run, a 50 mL round bottom flask with a magneticstir bar was charged with aldehyde (1 mmol), ophenylenediamine(1 mmol), Co/SBA-15 nanocatalyst(0.004 mmol, 0. 014 g) and ethanol (2 mL) under oxygenatmosphere at 60 C for 4 h. The progress of reaction wasmonitored by TLC (EtOAc: Hexane = 1:5). After reactioncompletion, the solvent was removed under vacuum and ethyl acetate (5 mL) was poured to the residue. Then, thereaction mixture was filtered off and the Co/SBA-15nanocatalyst was rinsed twice with EtOAc (10 mL) andreused; the filtrate was dried over sodium sulfate and thesolvent was removed under vacuum, the obtained solid waspurified by recrystallization in ethanol in a similar way tothat previously reported [28].
85% With C46H64CuN2O8Si2; In ethanol; at 50℃; for 3h; General procedure: A mixture of aldehyde (1.0mmol) and diamine (1.2mmol)was stirred in the presence of ethanol (5.0mL) as solvent andhomogeneous or heterogeneous catalytic system (5.0mol%) at 50C. Upon completion, nano-silica supported copper(II)complex was centrifuged. After separation of the catalyst,the organic layer was evaporated and then purified by silicagel column chromatography employing n-hexane/ethyl acetateas eluent.
81% With iodine; urea hydrogen peroxide adduct; In dimethyl sulfoxide; at 70℃; General procedure: To a stirred solution of theta-diaminoarene (1.0 mmol), aryl aldehyde (1.1 mmol), iodine (0.1 mmol), 20 mol% UHP and DMSO (5 mL) was heated to 70 C for specified time. After completion of the reaction as indicated by TLC, it was cooled to room temperature, aqueous sodium carbonate solution was added and extracted with EtOAc (2 × 25 mL). The combined organic layer were washed with brine solution (2 × 25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude. The crude was purified by silica gel column chromatography using ethyl acetate: hexane (3:7) to afford the pure product.

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  • 2
  • [ 98-98-6 ]
  • [ 95-54-5 ]
  • [ 1137-68-4 ]
YieldReaction ConditionsOperation in experiment
>= 85% With polyphosphoric acid; at 175℃;Inert atmosphere; General procedure: A diamine compound (0.05 mol) was mixed with a dicarboxylicacid or an acid anhydride (0.025 mol) and the mixture was poured into 50 ml of preheated (100C) polyphosphoric acid. The mixture was stirred and heated at 175C for 3-5 h. The reaction mixture was then poured in ice cold water and allowed to stand overnight.The precipitate was removed by filtration and washed several times with diluted sodium hydrogen carbonate solution and finally with water. The reaction product was then air dried and weighed.The products were characterized with NMR and mass spectroscopy (Table 4) and representative examples were characterized with elemental analysis (Table 3).
85% With polyphosphoric acid; at 180℃; for 6h;Inert atmosphere; A mixture of O-Phenylene diamine (0.1 mol, 10.89 g), 2-picolinic acid (0.1 mol, 12.3 g) and 120 mL of polyphosphoric acid(PPA) were stirred at 180 C for 6 h. (85% yield). M.p.: 224-226 C. 1HNMR (400 MHz, CDCl3) delta: 13.11 (s, 1H), 8.75-8.78 (m, 1H), 8.39-8.41(m, 1H), 8.02-8.04 (m, 1H), 7.76-7.77 (m, 1H), 7.25-7.60 (m, 4H). IR(KBr pellet, nu/cm-1): 3047 (w), 1598 (s), 1458 (s), 973 (m), 813 (s),770 (s).
56.7% With polyphosphoric acid; at 150℃; for 4h; Put 20 mL of polyphosphoric acid (PPA) into a double-necked flask, stir and preheat the solution to about 90 C. Then, slowly add about 2.46 g (about 0.02 mol) of 2-picolinic acid into the double-necked flask, and keep stirring the mixture evenly for about 30 minutes. Afterwards add about 2.16 g (about 0.02 mol) of o-phenylenediamine, then raise temperature to about 150 C. and keep stirring evenly the mixture for about 4 hours. When the reaction ends, lower the temperature of the mixture to about 100 C. Then, carefully and rapidly pour the reactant into iced water, and neutralize the mixture to weak alkalinity (about pH 9) with 1M sodium hydroxide (NaOH) solution. A pinkish purple color solid product is precipitated now. The solid is filtered out by suction, then it is dried by heat and purified by column chromatograph using a hexane/ethyl acetate (EA) solution (1:2) as eluent. About 2.21 g of white color solid is obtained with the yield of about 56.7%. The white solid product is 2-(pyridin-2-yl)-1H-benzimidazole.
52% With phosphoric acid; at 180℃; for 24h; Synthesis of 2-(2-Pyridyl)benzimidazole (L1)A solution of o-phenylenediamine (2.75 g, 25 mmol) and 2-picolinic acid (3.03 g, 24 mmol) was stirred o-phosphoric acid (30 mL) at 180 C for 24 h. Then solution was cooled at room temperature and added ammonia solution (% 25) until pH 9. The precipitate was filtered off and recrystallized from EtOH. Yield: 52%. m.p.: 110-112 C. 1H-NMR (400 MHz, DMSO-d6, ? ppm): 7.231-7.301 (2H, m, -Hf, -Hg); 7.534-7.599(2H, m, -Hb, -Hh); 7.746 (1H, d, J=6.8 Hz, -He); 8.029 (1H, m, -Hc); 8.377 (1H, dd, J1=7.8 Hz, J2=0.8 Hz, -Hd); 8.767 (1H, d, J=6.4 Hz, -Ha); 13.112 (1H, s, -NH). FT-IR(cm-1): 3057; 3012; 2968; 1593; 1569; 1440; 1400; 1315; 1280; 1261; 1228; 1122; 1911; 994; 971; 929; 903; 847; 797; 740; 701. UV (nm): 242; 288; 300 (???* and n??*). L2 Yield: 67%. m.p.:118 C. 1H-NMR (300 Mhz, CDCl3, ? ppm): 6.215 (2H, s, -Hi); 7.179-7.419 (9H, m, -Hj-l; -He-h); 7.802-7.908 (2H, m, -H7-8); 8.483 (1H, t, J=8.0 Hz, -Hb); 8.64 (1H, d, J=6.4 Hz, -Ha).13C-NMR (75 MHz, CDCl3, ? ppm) = ? 48.94 (-Ci); 110.82 (arom. -C); 120.17 (arom. -C); 121.79 (arom. -C); 122.83 (arom. -C); 123.60 (arom. -C); 123.88 (arom. -C); 124.61 (arom. -C); 124.73 (arom. -C); 126.84 (arom. -C); 127.37 (arom. -C); 128.60 (arom. -C); 136.88 (arom. -C); 137.40 (arom. -C); 137.49 (arom. -C); 142.78 (arom. -C); 148.47 (arom. -C); 149.08 (arom. -C); 150.01 (arom. -C); 150.58 (arom. -C); 150.90 (arom. -C). FT-IR(cm-1): 3040; 3016; 2973; 2908; 2882; 1609; 1590; 1568; 1440; 1395; 1315; 1279; 1166; 995; 793; 740; 697. UV (nm): 214; 302 (???* and n??*).L3 Yield: 68%. m.p.: 157 C. Anal. Calcd. for C23H23N3: C: 80.90; H: 6.79; N: 12.31%; found: C: 81.12; H: 6.72; N: 12.15%. 1H-NMR (300 MHz, CDCl3, ? ppm): 2.145 (6H, s, -Hj); 2.243 (6H, s, -Hk); 6.292 (2H, s, -Hi); 6.655 (1H, dt, J1=8.29 Hz, J2=0.94 Hz, -He); 6.992-7.047 (2H, m, -Hg; -Hl); 7.185-7.239 (1H, m, -Hf); 7.386 (1H, ddd, J1=7.54 Hz, J2= 4.9 Hz, J2= 1.13 Hz, -Hc); 7.802-7.832 (1H, m, -He); 7.896 (1H, td, J1=7.72 Hz, J2= 1.88 Hz,-Hb); 8.392-8.426 (1H, m, -Hd); 8.740 (1H, ddd, J1=4.8 Hz, J2=1.79 Hz, J3=0.94 Hz,-Ha). 13C-NMR (75 MHz, CDCl3, ? ppm) = ? 15.82 (-Cj); 20.61 (-Ck); 46.81 (-Ci); 111.91 (arom. -C); 119.96 (arom. -C); 122.17 (arom. -C); 123.21 (arom. -C); 123.74 (arom. -C); 125.33 (arom. -C); 131.80 (arom. -C); 132.39 (arom. -C); 133.78 (arom. -C); 134.11 (arom. -C); 136.44 (arom. -C); 136.97 (arom. -C); 142.84(arom. -C); 148.38 (-N=C< ipso (pyridine ring)); 150.77 (-Ca); 151.29 (-N=C-N ipso (benzimdazole ring). FT-IR(cm-1): 3049; 3017; 2969; 2914; 2864; 1612; 1591; 1566; 1466; 1437; 1387; 1331; 1207; 1167; 1010; 995; 902; 870; 790. UV (nm): 249 (???* and n??*).
43% With polyphosphoric acid; at 160℃; for 8h; 2-Picolinic acid (20.0 mmol) and 1,2-diaminobenzene (20.0 mmol) were added to 28 g PPA (polyphosphric acid),and stirred at 160 C for 8 h. The resulting viscous solution was poured into 500 mL water, producing a solid which was collected by suction filtration. The solid was suspended in 500 mL of aqueous 0.5 M Na2CO3, and filtered giving a pale yellow powder. Recrystallization from methanol/water. Yield: 43%, m.p.: 219 C, chemical formula (mol.wt.): C12H9N3 (195.22 g/mol), elemental analysis, calc. (%): C, 73.83; H, 4.65; N, 21.52, found: C, 73.75; H, 4.54; N, 21.43, 1H NMR: 8.213 (d, 2H, H4',5' ), 8.169 (d, 1H, H6'' ), 7.964 (dt, 1H, H4'' ), 7.737 (d, 1H, H3'' ), 7.699-7.592 (complex, 4H, H 3',6',1,5'' ), 13C NMR: 159.36 (C2'' ), 156.91 (C2), 146.76 (C6'' ), 137.35 (C2' ), 133.22 (C1' ), 130.54 (C4'' ), 129.50 (C5' ), 129.09 (C4' ), 128.55 (C3'' ), 128.30 (C3'), 127.41 (C6' ), 117.44 (C5'' ), FT-IR (KBr, cm-1): nu(NH), 3399 (s); nu(C-H), 3055 (m); nu(C=C), 1545 (s); nu(C=N), 1532 (s); delta(C-H), 741 (s).
General procedure: A mixture of o-phenylendiamine (1 eq) and the corresponding picolinic acid (1 eq), and 5-20 eq of polyphosphoric acid was stirred in an oil bath at 170 C for 4 h. The mixture was cooled to 100 C and then poured into rapidly stirred water. The pH was adjusted to 7 with NaHCO3. The solid was collected by filtration, and recrystallized from EtOAc to afford the corresponding products with 60-80% yields.
With polyphosphoric acid; at 150℃; for 8h;Inert atmosphere; The 2-pyridine-2-yl-1H-benzimidazole nucleus (compound 1) was synthesized by using equimolar quantities of picolinic acid and o-phenylenediamine, added to polyphosphoric acid (PPA) in 1:10 ratio and stirred under N2 at 150 C for 8 h. [33], [34] and [35] The resulting yellow solution was poured into water, the produced solid filtered and washed with 0.5 M sodium carbonate solution. Compounds 2-12 were synthesized by treating compound 1 with equimolar quantities of each of the other halogenated acetophenones with various substitutions (Fig. 1). Compound 1 and acetophenone reactants dissolved in acetone were mixed and refluxed for 4 h. The products in the form of precipitates were collected and recrystallized by ethanol and diethyl ether
With polyphosphoric acid; at 220℃; for 6h; Benzene-1, 2-diamine and picolinic acid were heated to 220 C using polyphosphoric acid (PPA) as catalyst, as described in Ref. [16]. 1H NMR (600 MHz, DMSO): delta 13.09(1H, s), 8.74(1H, d), 8.33(1H, dd), 8.01(1H, dt), 7.71(1H, d), 7.52-7.55 (2H, m), 7.26-7.20(2H, m); FT-IR (KBr) cm-1: 3322, 3245, 3054, 1593, 1492, 1417, 1319, 1259, 1130, 1037, 840, 798, 734, 522, 468.
With polyphosphoric acid; at 175℃; A diamine compound (0.05mol) was mixed with a dicarboxylic acid or an acid anhydride (0.025mol) and the mixture was poured in 50ml of preheated (100C) polyphosphoric acid. The mixture was stirred and heated at 175C for 3-5h. The reaction mixture was then poured in ice cold water and allowed to stand overnight. The precipitate was removed by filtration and washed several times with diluted sodium hydrogen carbonate solution and finally with water. The reaction product was then air dried, weighed and characterized by NMR and mass spectroscopy (Table 4). Representative samples were characterized by elemental analysis (see Table 3).
Methanesulfonic acid, sulfolane and water will be charged into a flask fitted with a magnetic stirrer, reflux condenser, and a temperature probe. To this, o-phenylenediamine (12.96 g, 1 equiv.) and Picolinic acid (15.51, 1.05 equiv.) will be added and the contents of the flask will be refluxed at about 110 C. After 8 h reflux time acetic acid (2 g) will be added and reflux will be maintained for additional about 3 hours to obtain the title compound.

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[13]Polyhedron,2015,vol. 85,p. 926 - 932
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[16]Chemistry - A European Journal,2007,vol. 13,p. 7432 - 7442
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[18]Analytical Chemistry,1954,vol. 26,p. 217,218
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[33]Patent: US2019/144395,2019,A1 .Location in patent: Paragraph 0155; 0156
  • 3
  • [ 1137-68-4 ]
  • [ 2595-90-6 ]
  • [ 810676-76-7 ]
  • 4
  • [ 1137-68-4 ]
  • [ 939-26-4 ]
  • [ 810676-74-5 ]
YieldReaction ConditionsOperation in experiment
78% The 2-(pyridin-2-yl)-1H-benzo[d]imidazole (2.0g, 0.0102 mol)was dissolved in 30 ml of dry DMF and stirred with potassiumcarbonate (1.4g, 0.0102 mol) at room temperature for 1 h and 2-(Bromomethyl naphthalene) (2.2. g, 0.0102 mol) was dissolved in20 ml of THF then added dropwise using dropping funnel proceedthe reaction for further 12 h. The proceeding of product waschecked by thin layer chromatography. After the completion ofreaction solvent was rescued under vacuum, the resulting solidswere treated with 30 ml of HCl washed using ethyl acetate anddistilled water. The separated organic layer is filtered over sodiumsulphate then the compound was purified under column chromatographytechnique (Hexane: ethyl acetate-10:90) to obtain whitesolid as the product. Yield 78%, 1H NMR (500 MHz, CDCl3) d 8.51 (d,J 4.3 Hz, 1H), 8.37 (d, J 8.0 Hz, 1H), 7.85e7.52 (m, 5H), 7.45 (s,1H), 7.33e7.05 (m, 7H), 6.25 (s, 2H). 13C NMR (126 MHz, CDCl3)d 150.52, 150.01, 148.68, 142.72, 136.92, 134.97, 133.29, 132.71,128.45, 127.81, 127.61, 126.22, 125.88, 125.40, 124.89, 124.75, 123.92,123.69, 122.93, 120.16, 49.20. HRMS (ESI): calcd. For [MH]C23H17N3 336.1495 found 336.1497. The data is given in supp. data eFig. S4aec.
  • 5
  • [ 1137-68-4 ]
  • [ 7511-49-1 ]
  • [ 887110-26-1 ]
  • 6
  • [ 1137-68-4 ]
  • [ 100726-39-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: butyllithium / tetrahydrofuran / 3 h / -78 °C 1.2: 70 percent / tetrahydrofuran / 3 h / Heating 2.1: 97 percent / NaOH / ethanol; H2O / 0.67 h
Multi-step reaction with 2 steps 1: K2CO3 2: aqueous Ba(OH)2
  • 7
  • [ 1121-60-4 ]
  • [ 95-54-5 ]
  • [ 1137-68-4 ]
  • [ 14132-58-2 ]
YieldReaction ConditionsOperation in experiment
74% With cerium(III) nitrate hexahydrate; In N,N-dimethyl-formamide; at 80℃; for 2.5h; General procedure: Ce(NO3)3·6H2O (0.15 mmol) was added to a mixture of the diamine 1 (0.5 mmol) and the appropriate aldehyde 2 (0.6 mmol) in DMF (3 mL). The reaction mixture was stirred at 80C. The reaction progress was monitored by TLC. After complete consumption of the starting materials, the reaction mixture was cooled to rt, water (15 mL) was added and the resulting mixture was extracted with EtOAc (3 10 mL). The combined organic phases were successively washed with water and brine, and dried over anhydrous MgSO4. After filtration, the solvent was removed under reduced pressure. The product was purified chromatographically (hexane- EtOAc, 70:30).
  • 8
  • [ 1137-68-4 ]
  • [ 343308-57-6 ]
  • [ 1187383-63-6 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 48h; General procedure: To a solution of 16a (521 mg, 1 mmol) in dry DMF (10 mL) was added anhydrous K2CO3 (552 mg, 4 mmol) and the <strong>[1137-68-4]2-(2-pyridyl)benzimidazole</strong> 7a (195 mg, 1 mmol). The reaction mixture was stirred at room temperature for 48 h. Potassium carbonate was removed by suction filtration and the filtratewas concentrated under vacuum. The crude product was purifiedby column chromatography using 3% MeOH-CHCl3 aseluent to afford pure compound 17a as a brown solid.
75% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 48h; EXAMPLE 9 To a solution of (2S)-N-[4-(5-bromopentyl)oxy-5-methoxy-2-nitrobenzoyl) pyrrolidine-2-carboxarbaldehyde diethyl thioacetal 2c (549 mg, 1 mmol) in dry DMF (10 ml_) was added anhydrous K2CO3 (552 mg, 4 mmol) and the 2-(2- pyridyl)benzimidazole 4a (195 mg, 1 mmol). The reaction mixture was stirred at room temperature for 48 h. TLC using ethyl acetate as a solvent system monitored the reaction. The potassium carbonate was removed by suction filtration and the solvent was removed under vacuum. The crude product was purified by column chromatography using 2% MeOH-CHCI3 as eluent to afford pure compound of 9b (498 mg, 75%). 1H NMR (CDCI3): 8.62 (d, J = 5.1 Hz, 1 H), 8.44 (d, J = 8.0 Hz, 1 H), 7.75-7.87 (m, 2H), 7.47-7.51 (m, 1 H), 7.45 (s, 1H), 7.20-7.35 (m, 3H), 6.77 (s, 1 H), 4.82 (d, J = 3.7 Hz, 1 H), 4.57-4.71 (m, 3H), 4.02-4.15 (m, 2H), 3.97 (s, 3H), 3.10-3.30 (m, 1 H), 2.90-3.08 (m, 1 H), 2.65-2.85 (m, 4H), 2.45-2.62 (m, 2H), 1.60-2.40 (m, 6H), 1.44-1.50 (m, 2H), 1.30-1.42 (m, 6H) ESIMS: m/z 666 (M+).
  • 10
  • [ 1137-68-4 ]
  • [ 4761-00-6 ]
  • [ 1245631-71-3 ]
YieldReaction ConditionsOperation in experiment
85% General procedure: In a two-necked, 100-mL round-bottom flask equipped with a blanket of nitrogen (N2) was placed 30mL of anhydrous toluene or tetrahydrofuran (THF) at room temperature for each ligand. KOH (0.56 g, 10.0mmol) was added to these solutions, then a solution of 2-pyridylbenzimidazole (1.95 g, 10.0 mmol) in anhydrous toluene (10 mL) was slowly added and stirred at reflux for 6 h. To these solutions, benzyl halides were added such as 2,4,6-trimethylbenzyl bromide (2.13 g, 10.0 mmol) for ligand 2A1 , 2,3,4,5,6-pentamethylbenzylbromide(2.45 g, 10.0 mmol) for ligand 2A2, 1,2-bis(bromomethyl)benzene (1.32 g, 5.0 mmol) for ligand 3B1, 2,4-bis(bromomethyl)-1,3,5-trimethylbenzene (1.53 g, 5.0 mmol) for ligand 3B2, 1,4-bis(bromomethyl)-2,3,5,6-tetramethylbenzene (1.60 g, 5.0 mmol) for ligand 3B3, and 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene(1.33 g, 3.3 mmol) for ligand 4C1, respectively, and then heated under reflux for 24 h. The volatiles were evaporated in vacuum to dryness. The residue was dissolved in CH2Cl2 and filtered via cannula on Celite. The solution was concentrated to 15 mL and then the desired product was precipitated in 30 mL of n-hexane.
  • 11
  • [ 1137-68-4 ]
  • [ 578743-87-0 ]
  • (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Cu(2-(2-pyridyl)benzimidazole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.5% 2-(2-Pyridyl)benzimidazole (78.1 mg, 0.4 mmol) was dissolved in 10 mL of dry THF under N2 and this solution was transferred via cannula to suspension of sodium hydride (17.6 mg, 0.44 mmol, 60% in mineral oil) in dry THF. Reaction mixture was stirred at RT for 1 h and then chloro[l,3-bis(2,6-di-i-propylphenyl)imidazol-2- ylidene]copper(I) (195.1 mg, 0.4 mmol) was added. Reaction mixture was stirred at RT for 3 h. The resulting mixture was filtered through Celite and solvent was removed by rotary evaporation. Recrystallization by vapor diffusion of Et20 into a CH2C12 solution of product gave 154 mg (59.5%>) of dark yellow crystals. Anal, calcd. for C39H44CuN5: C, 72.47; H, 6.86; N, 10.48; Found: C, 72.55; H, 6.94; N, 10.84.
  • 12
  • [ 1137-68-4 ]
  • samarium(III) chloride hexahydrate [ No CAS ]
  • [ 893-33-4 ]
  • [Sm(4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedionate)3(2-(2-pyridine)-benzimidazole)] [ No CAS ]
  • 13
  • [ 1137-68-4 ]
  • europium(III) chloride hexahydrate [ No CAS ]
  • [ 893-33-4 ]
  • [Eu(4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedionate)3(2-(2-pyridine)-benzimidazole)] [ No CAS ]
  • 14
  • [ 1137-68-4 ]
  • [ 873779-78-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 2-(2'-pyridyl)benzimidazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere; Stage #2: chloro[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I) In tetrahydrofuran; mineral oil at 20℃; for 3h; Inert atmosphere; 6 2-(2-Pyridyl)benzimidazole (78.1 mg, 0.4 mmol) was dissolved in 10 mL of dry THF under N2 and this solution was transferred via cannula to suspension of sodium hydride (17.6 mg, 0.44 mmol, 60% in mineral oil) in dry THF. The reaction mixture was stirred at RT for 1 h and then chloro[l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]copper(I) (161.4 mg, 0.4 mmol) was added. The reaction mixture was stirred at RT for 3 h. The resulting mixture was filtered through Celite. Solvent was removed by rotary evaporation and 178 mg (79%>) of light-yellow solid was obtained.
  • 15
  • [ 629-03-8 ]
  • [ 1137-68-4 ]
  • [ 1312598-25-6 ]
YieldReaction ConditionsOperation in experiment
90% WeighPyridylbenzimidazole1 mmol of 195 mg and 660 mg of potassium hydroxide in a total amount of 336 mg were placed in a 50 mL eggplant-shaped bottle, and after degassing three times with a double-row tube, three times of ionic liquid was injected.The reaction system was protected with nitrogen and stirred at room temperature for 4 h.The reaction was continued for 8 h by injecting 0.8 mL of dibromohexane.After the reaction, it was extracted with water and dichloromethane.The column is purified to give a colorless oily liquid product.Yield: 90%.
60% With potassium hydroxide; for 5h; adding potassium hydroxide in the reaction bottle 51mmol and 2 - pyridine benzimidazole 10.2mmol, and into ionic liquid 20 ml. Mixture pre-stirring 5 minutes, add 1, 6 - two hexyl bromides 8 ml, stirring at room temperature the reaction 5h. After the reaction is finished, the extraction three times with ethyl ether, combined oil phase, using rotary evaporator to remove the solvent. The obtained crude product was column chromatography separation, showering liquid is petroleum ether: ethyl acetate=3:1, to obtain the colorless oily liquid 2.2g, yield 60%.
60% Potassium hydroxide 51 mmol and 2-pyridylbenzimidazole were added to the reaction flask10.2 mmol, and 20 ml of 1-butyl-3-methylimidazolium hexafluorophosphate (ionic liquid) was added. After the mixture was stirred for 5 min in advance, 8 ml of 1,6-dibromohexane was added and the reaction was stirred for 5 h. After the reaction is complete, extract three times with ether, combine the oil phases, and use rotationThe evaporator removes the solvent. The resulting crude product was separated by column chromatography. The volume ratio of the eluent was petroleum ether:ethyl acetate=A 3:1 mixed solution finally gave 2.2 g of a colorless oily liquid with a yield of 60%.
  • 16
  • [ 1137-68-4 ]
  • [ 23915-07-3 ]
  • C19H13F2N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.3% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h; Mix about 0.195 g (about 1 mmol) of the white solid product obtained in Step 1, about 0.276 g (about 2 mmol) of K2CO3, and about 15 mL of N,N'-dimethylformamide (DMF) in a reaction vessel and keep stirring for about 10 minutes. Then, carefully inject about 0.385 mL (about 3 mmol) of 2,4-difluorobenzyl bromide into the mixture by a syringe and let the mixture react for about 3 hours at room temperature. When the reaction ends, pour the reactant into iced water and extract using EA. Then collect and dehydrate the organic layer using anhydrous sodium sulfate. After filtration and concentration, a yellow color viscous liquid is obtained. Then purify the yellow viscous liquid by column chromatograph using a hexane/EA solution (3:1) as eluent. Then, dry it by vacuum suction and collect about 0.242 g of beige-white color solid (i.e. the ligands L1) . The yield is about 75.3%.
  • 17
  • [ 3731-51-9 ]
  • [ 95-54-5 ]
  • [ 1137-68-4 ]
YieldReaction ConditionsOperation in experiment
86% With iron(III) chloride; 3-methyl-4-oxa-5-azahomoadamantane; oxygen; In water; at 100℃; for 16h; General procedure: A mixture of 1.2 mmol o-phenylenediamine, 2-aminophenol or 2-aminothiophenol and 1 mmol primary amine, 10 mol % FeCl3, 1 mol % 3-methyl-4-oxa-5-azahomoadamantane, 5 ml H2O were mixed in a 10-ml three-necked flask, then O2 was bubbled into the flask at flow rate of 20 ml/min. The reaction mixture was stirred at 100 C for several hours, and reaction progress was monitored by TLC. The final reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was directly purified by column chromatography on silica gel using hexane/ethyl acetate (7:3) as eluent to afford the pure product.
69% With iron(III) sulfate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In neat (no solvent); at 110℃; for 30h;Green chemistry; General procedure: A mixture of 6 mmol of the alcohol or the amine and5 mmol o-phenylenediamine, o-aminophenol or o-aminothiophenol,10 mol % Fe2(SO4)3, 10 mol % TEMPO wasprepared in a 10 ml three-necked flask, and then stirred inopen air at 110 C for several hours, The reaction progresswas monitored by TLC. When the final reaction mixturecooled to room temperature, the crude products was directlypurified by column chromatography on silica gel using hexane/ethyl acetate (7:3) as eluent to afford the pure product.
68% With tert.-butylhydroperoxide; In water; at 100℃; for 10h; General procedure: A mixture of 1.5 mmol aromatic amines, 1 mmol o-phenylenediamine, and 4 mmol TBHP were prepared in a 10-ml, three-necked flask, stirred at 100 C for several hours, and the reaction progress was monitored by TLC. After completionof the reaction, the reaction mixture was cooled to room temperature. The pure product was isolated after a simple filtration. When necessary, the crude product was purified by chromatography using hexane/ethyl acetate (7:3) as eluent.
  • 18
  • [ 1137-68-4 ]
  • [ 5535-49-9 ]
  • 1-(2-(phenylthio)ethyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole [ No CAS ]
  • 19
  • [ 1137-68-4 ]
  • [ 70197-13-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; 4.3 Synthesis of MTO complexes General procedure: All MTO complexes were synthesized according to a general procedure: a solution of MTO (0.05 g, 0.2 mmol) in CH2Cl2 (2 mL) was drop-wise added to an equally concentrated solution of ligand (L1-L7) in CH2Cl2 (5 mL) under stirring at room temperature. For 1, 2, 5 a yellow precipitate formed rapidly. The precipitate was isolated by filtration, washed with n-hexane and dried under reduced pressure. For 3, 4, 6, 7, the reaction mixture was stirred for 1 h at room temperature before removing the solvent in vacuum. The remaining solid was washed with n-hexane twice and dried under reduced pressure.
  • 20
  • [ 1137-68-4 ]
  • [ 845659-67-8 ]
  • [ 1431507-42-4 ]
YieldReaction ConditionsOperation in experiment
81% Under N2, solid NaH (60% dispersed in mineral oil, 0.120 g) and <strong>[1137-68-4]2-(2-pyridyl)benzimidazole</strong> (0.680 g, 0.0035 mol) in 20 mL of anhydrous DMF was stirred at 80 C for 2 h. The resulting solution was cooled to room temperature and 9-(4-(bromomethyl)penyl)-9H-carbazole (1.400 g, 0.0042 mol) was added. The mixed solution was stirred at 80 C for 36 h. After completing, the reaction mixture was poured into 100 mL of cool water, and was extracted with dichloromethane (3 × 50 mL). The organic phase was washed with water and dried over anhydrous MgSO4. After removal of solvent, the residue was purified by column chromatography using ethyl acetate/petroleum ether (1: 4, v/v) as the eluent to give a white powder. Yield: 81%. m.p.:186-188 C. IR (KBr pellet cm-1): 3041 (Aryl-CH), 2931 (-CH2-), 1614, 1456, 1328, 1150, 750. 1H NMR(CDCl3, delta, ppm): 8.70 (d, 1H, J = 7.4 Hz, Aryl-H), 8.50 (d, 1H, J = 8.0 Hz, Aryl-H), 8.11 (d, 2H, J = 7.6 Hz, Aryl-H), 7.92-7.86 (m, 2H, Aryl-H), 7.48-7.41 (m, 5H, Aryl-H), 7.38-7.33 (m, 7H, Aryl-H), 7.25 (t, 2H, J = 8.8 Hz, Aryl-H), 6.32 (s, 2H, N-CH2-Ar). Anal. Calc. for C31H22N4 (%): C, 82.64; H, 4.92; N, 12.44. Found: C, 82.38; H, 5.01; N, 12.52.
  • 21
  • [ 1137-68-4 ]
  • [ 7718-98-1 ]
  • [ 1428543-10-5 ]
YieldReaction ConditionsOperation in experiment
78% In ethanol for 5h; Reflux; 3 cis-[VO2(Hpybz)(pybz)] (1) An ethanolic solution (20 cm3) of Hpybz (0.248 g, 1.271 mmol) and VCl3 (0.100 g, 0.636 mmol) was heated to refluxed for 5 h. The volume of the resultant dark green solution was reduced to half and layered with petroleum ether. Dark green cubic crystals were obtained which were suitable for X-ray analysis, yield (78%).
  • 22
  • [ 1137-68-4 ]
  • copper(II) choride dihydrate [ No CAS ]
  • [ 556-50-3 ]
  • [Cu(glycylglycine)(2-(2-pyridyl)benzimidazole)(Cl)]*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: copper(II) choride dihydrate; glycylglycine With sodium hydroxide In water at 60℃; for 0.5h; Stage #2: 2-(2'-pyridyl)benzimidazole In ethanol; water at 60℃; for 3h; Synthesis of [Cu(glygly)(HPB)(Cl)]⋅2H2O To an aqueous solution of glygly (0.066 g, 0.5 mmol) and NaOH (0.020 g, 0.5 mmol) was added an aq. soln. of CuCl2⋅2H2O (0.085 g, 0.5 mmol) with stirring, followed by the addition of HPB (0.097 g, 0.5 mmol) in ethanol (20 mL). The stirring was continued for ca. 3 h at 60 °C. The resulting solution was filtered off and allowed to evaporate for a few days at room temperature until solid precipitate formed. The resulting product was filtered, dried under vacuum, and further purified by recrystallization from 80% ethanol-water (v/v). Yield: 0.13 g, 58%. Anal. Calc. for C16H20ClN5O5Cu (%): C, 41.65; H, 4.37; N, 15.18. Found (%): C, 41.29; H, 4.49; N, 14.97. IR (KBr, cm-1): 3448 ν(-OH), 3228 νas(-NH2), 3072 νs(-NH2), 1629 νas(-COO-), 1594 ν(C=N), 1459 ν(C=C), 1385 νs(-COO-), 756 ν(=CH), 623 ν(Cu-Cl), 485 ν(Cu-O), 432 ν(Cu-N). Molar conductance, ΛM (1 * 10-3 M, MeOH) = 61.2 Ω-1 cm2 mol-1. UV-vis (MeOH) λ/nm (ε/M-1 cm-1): 233 (12,566), 320 (13,074) and 655 (79.77). ESI-MS (m/z, MeOH): 426.8 [MH]+.
  • 23
  • [ 755027-18-0 ]
  • [ 1137-68-4 ]
  • [ 1562339-28-9 ]
YieldReaction ConditionsOperation in experiment
1.25 g A mixture of 2-(2-pyridyl)benzimidazole (287 mg, 1.469 mmol), cesium carbonate (5.98 g,18.36 mmol), copper(l) iodide (280 mg, 1.469 mmol) and DMF (5 ml) were combined in a5 microwave vial fitted with an N2 inlet and magnetic stir bar. The slurry was heated at 60 oc for 1 h,followed by addition of imidazole (500 mg, 7.34 mmol) and <strong>[755027-18-0]1-bromo-4-iodo-2-methoxybenzene</strong> (2.3g, 7.34 mmol). The reaction mixture was heated at 90 oc for 2 days. The reaction mixture wasfiltered through celite, washed with EtOAc, and concentrated in vacuo. The crude material waspurified by silica gel chromatography (10% to 40% EtOAc in heptanes) to give 1-(4-bromo-3-10 methoxyphenyl)-1 H-imidazole (1.25 g, MS: 255.2 [M+H+])
  • 24
  • [ 13191-36-1 ]
  • [ 1137-68-4 ]
  • 2-bromo-5-[2-(2′-pyridyl)benzimidazolyl]-3-methylthiophene [ No CAS ]
  • 25
  • [ 1137-68-4 ]
  • [ 102429-07-2 ]
  • 1-[2-(2',4'-difluorophenyl)-2-oxoethyl]-2-(2-pyridinyl)-1H-benzimidazol-1-ium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% In acetone Reflux;
30% In acetone Reflux; Chemistry General procedure: In conical flask the corresponding substituted phenacylhalides and 2-(2'-pyridyl) benzimidazole (Ia) were dissolvedin equimolar quantities (0.01 mol) separately in15-20 mL acetone and all were mixed in a round bottomflask together. The reaction mixture was stirred on magneticstirrer for four h and then refluxed on water bath forabout 5-6 h. Completion of reaction was monitored by thinlayer chromatography. As a results the precipitates productswere filtered and washed with warm acetone in orderto remove the unreacted starting material. To improvecolor and shape of crystals and to ensure purity, the precipitatesof each product were re-crystallized at least threetimes. Vacuum desiccator was used for purification and thepure compounds were dried in over anhydrous calciumsulfate.
In acetone Reflux;
  • 26
  • [ 1137-68-4 ]
  • [ 106-96-7 ]
  • 1-propargyl-2-pyridylbenzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% To a stirred suspension of sodium hydride (2.4 mmol) in anhydrousTHF (5 mL), a solution of 2-pyridyl-benzimidazole (0.390 g,2 mmol) in anhydrous THF (5 mL) was added drop-wise at 0 C.The reaction mixture was stirred for 30 min. To this suspension,propargyl bromide (3.0 mmol, 1.5 equiv.) was added and allowedto stir overnight. The reaction mixture was quenched with methanoland evaporated to dryness. The residue was extracted withCH2Cl2 (2 5 mL) and the combined organic layers were dried overNa2SO4. The solvent was removed under reduced pressure, affordingthe crude alkyne as a white solid. The compound was furtherpurified by alumina column chromatography using a hexane-ethylacetate (9:1) solvent mixture.Yield: 0.35 g (90%); mp: 127 C; IR (KBr, tmax/cm1) = 3448,3152, 3047, 2988, 2107, 1586, 1613, 1508, 1274, 617; 1H NMR(300 MHz, CDCl3, Me4Si): d 2.29 (t, 1H, J = 2.3 Hz, alkyne), 5.89 (d,2H, J = 2.3 Hz, CH2), 7.31-7.42 (m, 3H, Ar), 7.61 (dd, 1H, J = 5.3and 1.5 Hz, Ar), 7.83-7.89 (m, 2H, Ar), 8.45 (dd, 1H, J = 7.6 and1.5 Hz, Ar), 8.73 (d, 1H, J = 5.3 Hz, Ar); 13C NMR (75.5 MHz,CDCl3): d 35.11, 72.70, 78.19, 110.46, 120.17, 123.02, 123.72,123.93, 124.57, 136.15, 136.93, 148.57 ppm; ESI-MS (in CH3OH):m/z = 234 [M + H]+; Anal. Calc. for C15H11N3: C, 77.23; H, 4.75; N,18.10. Found: C, 77.08; H, 4.51; N, 17.92.
  • 27
  • copper(II) perchlorate hexahydrate [ No CAS ]
  • [ 1137-68-4 ]
  • [ 3316-09-4 ]
  • [Cu(2-(2-pyridyl)benzimidazole)(4-nitrocatecholate)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% In acetonitrile; at 20℃; for 20h;Inert atmosphere; General procedure: Copper complexes of all the N-donor ligands with <strong>[3316-09-4]4-nitrocatechol</strong>have been synthesized in a similar manner. The ligand (3.0 mmol), <strong>[3316-09-4]4-nitrocatechol</strong> (3.0 mmol) and Cu(ClO4)2*6H2O (3.0 mmol) were dissolved in 30 ml dry acetonitrile under Ar. The mixture was stirred for 20 h at RT. The precipitated product was washed with diethyl ether (3x10 ml) after filtration. Yield: 1.2 g (97%). IR (KBr) cm-1: 3420 m, 1607 w, 1506 m, 1456m, 1245 s, 1199 s, 1116 m, 1077 w, 750 w, 638 w. UV-Vis (DMF) lambdamax (nm, log epsilon): 459 (3.87), 344 (4.15), 325 (4.32) 313 (4.32) 288(4.25). C18H12CuN4O4: Calc. C, 52.49; H, 2.94; N, 13.60. Found: C,52.51; H, 2.97; N, 13.60%.
  • 28
  • [ 1137-68-4 ]
  • [ 4761-00-6 ]
  • C22H21Cl2N3Pd [ No CAS ]
  • 29
  • [ 1137-68-4 ]
  • [ 1204-21-3 ]
  • 1-[2-(2',5'-dimethoxyphenyl)-2-oxoethyl]-2-(2-pyridinyl)-1H-benzimidazol-1-ium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% In acetone;Reflux; General procedure: In conical flask the corresponding substituted phenacylhalides and 2-(2'-pyridyl) benzimidazole (Ia) were dissolvedin equimolar quantities (0.01 mol) separately in15-20 mL acetone and all were mixed in a round bottomflask together. The reaction mixture was stirred on magneticstirrer for four h and then refluxed on water bath forabout 5-6 h. Completion of reaction was monitored by thinlayer chromatography. As a results the precipitates productswere filtered and washed with warm acetone in orderto remove the unreacted starting material. To improvecolor and shape of crystals and to ensure purity, the precipitatesof each product were re-crystallized at least threetimes. Vacuum desiccator was used for purification and thepure compounds were dried in over anhydrous calciumsulfate.
  • 30
  • copper(II) perchlorate hexahydrate [ No CAS ]
  • [ 1137-68-4 ]
  • [ 1963-21-9 ]
  • [Cu(Gly-L-val)(2-(2'-pyridyl)benzimidazole)(H2O)]*ClO4*1.5H2O [ No CAS ]
  • 31
  • [ 586-98-1 ]
  • [ 88-74-4 ]
  • [ 1137-68-4 ]
YieldReaction ConditionsOperation in experiment
74% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In toluene; at 160℃; for 24h;Schlenk technique; Inert atmosphere; Sealed tube; General procedure: GeneralProcedure for the preparation of 2-Phenyl-1H-benzoimidazole (3aa): A 25mL over-dried Schlenk tube was charged with 2-nitroaniline (41.4 mg, 0.3 mmol),benzyl alcohol (97.2 mg, 0.90 mmol) and Pd(dppf)Cl2 (12.2 mg, 0.015mmol). The tube was purged with nitrogen three times. Toluene (1 mL) was addedto the sealed reaction vessel by syringe. The reaction mixture was stirred in apreheated oil bath at 160 oC for 24 h. After cooling to roomtemperature, the reaction mixture was then concentrated in vacuo, and theresidue was purified by column chromatography (silica gel, petroleumether/ ethyl acetate = 4:1) to give 3aa as a pale yellow solid (56.5 mg, 97%).
45% With 1,1'-bis-(diphenylphosphino)ferrocene; In toluene; at 150℃; for 24h;Inert atmosphere; Sealed tube; General procedure: The preparation of 2-phenyl-1H-benzoimidazole (3a): A 15 mL capped tube was charged with 2-nitroaniline (0.36 mmol), benzyl alcohol (0.094 mL, 0.90 mmol) and dppf (0.018 mmol). The tube was flushed with argon for 10 min. Then the degassed toluene (3 mL) was added. The tube was flushed with argon, capped, and heated at 150 C for 24 h. After cooling to room temperature, the reaction mixture was then concentrated in vacuo, and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to afford the pure 3a as a white solid. The product was identified by NMR and MS and the data are identical to the reported values.
  • 32
  • [ 1137-68-4 ]
  • [ 6959-48-4 ]
  • 2-(pyridin-2-yl)-1-(pyridin-3-ylmethyl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% S11, weighed 0.7150g 2-pyridine benzimidazole to 100mL three-necked flask,Add 30mL of dehydrated acetone,Then add 0.6mL of PEG-400, 0.9250g of K2CO3, respectively.0.0925 g of KI was stirred at room temperature for 30 minutes. Weigh 0.5100 g of 3-chloromethyl pyridine hydrochloride in a 25-mL Erlenmeyer flask.Add 10 mL of acetone, which has been dehydrated, and stir at room temperature for 30 minutes.Add acetone solution of 3-chloromethyl pyridine hydrochloride to the three-neck flask.60 reflux reaction 12h, hot filtrate to take the filtrate;S12. Slowly add the filtrate to pure water in a ratio of v/v=1:40 until the solution is about to turn red.2-3 days at room temperature can be observed with brown needle crystal precipitation, filtration,Dry at room temperature to give ligand (ppbm); Yield: 75%.
  • 33
  • [ 3512-17-2 ]
  • [ 1137-68-4 ]
  • C41H26N10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate; In dimethyl sulfoxide; at 150℃; for 12h; <strong>[3512-17-2]2,4,6-trifluoropyridine</strong> (0.5 g, 3.76 mmol), potassium carbonate (5.19 g, 37.6 mmol), 2-pyridylbenzimidazole (2.42 g, 12.4 mmol), DMSO 8 ml, heated at 150 C for 12 h . The mixture was cooled to room temperature and poured into 200 ml of water to precipitate a large amount of solid. The mixture was stirred for 0.5 h, and filtered to give a white solid. After purification by column chromatography, ethanol was recrystallized to give white solid 1.75 g, yield 70%.
  • 34
  • [ 1137-68-4 ]
  • [ 14516-54-2 ]
  • C15H9BrMnN3O3 [ No CAS ]
  • 35
  • [ 7681-65-4 ]
  • [ 1137-68-4 ]
  • [ 13885-09-1 ]
  • C36H28CuIN3P [ No CAS ]
YieldReaction ConditionsOperation in experiment
48.5% In dichloromethane; acetonitrile; for 0.0833333h; A solution of CuI (0.019 g, 0.1 mmol) in CH3CN(5 mL)was added to a stirred solution of 2-PBI (0.020 g, 0.1 mmol)and 2-(Dpp)bp (0.034 g, 0.1 mmol) in CH2Cl2(5 mL). Themixture was stirred for 5 min, with no visible precipitation.After filtration, the filtrate was set aside for evaporation inair. Yellow block crystals of complex 3 were obtained after3 days. Yield: 35.1 mg (48.5percent, based on Cu). Anal. Calc. for3 C36H28N3P1Cu1I1:C, 59.73; H, 3.87; N, 5.81. Found (percent):C, 59.72 H, 3.84; N, 5.78. IR (KBr pellet, cm?1): 3443sh,3077vs, 3054s, 1610w, 1491m, 1443vs, 1326m, 1114w,805m, 746vs, 711vs, 522m.
  • 36
  • [ 1137-68-4 ]
  • [ 874-77-1 ]
  • 2-(1H-benzo[d]imidazol-2-yl)nicotinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With potassium phosphate; copper diacetate In N,N-dimethyl-formamide at 130℃; for 6h;
  • 37
  • [ 31191-08-9 ]
  • [ 95-54-5 ]
  • [ 1137-68-4 ]
YieldReaction ConditionsOperation in experiment
70% With sodium thiosulfate; In water; N,N-dimethyl-formamide; at 90℃;Cooling with ice; O-phenylenediamine (5.24 g, 48 mmol) of pyridinecarboxaldehyde (4.37 g, 40 mmol) was dissolved in DMF, respectively, and an aqueous solution of sodium thiosulfate (7.92 g, 40 mmol) was added thereto, and the mixture was heated to 90 C overnight in an oil bath. At the end of the reaction, the reaction was poured into water to give the product A2, yield 70%.
  • 38
  • [ 1137-68-4 ]
  • [ 2595-90-6 ]
  • C40H27ClN4Pt [ No CAS ]
  • 39
  • [ 1137-68-4 ]
  • [ 526-95-4 ]
  • [ 7732-18-5 ]
  • [ 6046-93-1 ]
  • [Cu(Gluc)(HPB)(H2O)]Gluc [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 50℃; for 1h; 4.2 Synthesis of the complexes General procedure: 2-(2′-pyridyl)benzimidazole (HPB) and 5-chloro-2-(2′-pyridyl)benzimidazole (HPBC) were synthesized as previously reported [21,22]. To a solution of HPB/HPBC (0.5mmol) in EtOH (20mL) was added an equimolar amount of copper acetate, and the d-gluconic acid (2mmol) dissolved in H2O (1mL) was added subsequently. After being stirred and heated at 50°C for 1h, the resulting solution was slowly evaporated at room temperature. The obtained sample was recrystallized with 90% ethanol-water solution, and then collected and washed with a small amount of anhydrous ethanol. The purity of the complexes was detected by HPLC (Agilent 1290 infinity I) system combined with DAD detector, and the experimental results showed that the purity of the two complexes exceeded 98% (Fig.S10 and S11).
  • 40
  • [ 14243-64-2 ]
  • [ 1137-68-4 ]
  • [ 1359998-80-3 ]
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