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[ CAS No. 37734-89-7 ] {[proInfo.proName]}

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Chemical Structure| 37734-89-7
Chemical Structure| 37734-89-7
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Product Details of [ 37734-89-7 ]

CAS No. :37734-89-7 MDL No. :MFCD06660149
Formula : C16H14N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 234.30 Pubchem ID :-
Synonyms :

Safety of [ 37734-89-7 ]

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Precautionary Statements: UN#:
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Application In Synthesis of [ 37734-89-7 ]

* 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 [ 37734-89-7 ]

[ 37734-89-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 37734-89-7 ]
  • [ 670-96-2 ]
YieldReaction ConditionsOperation in experiment
94% With potassium <i>tert</i>-butylate; oxygen; dimethyl sulfoxide at 25℃; for 0.25h;
45% With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; General Procedure: General procedure: A 16 mL vial with a PTFE/silicone septum and a nitrogen-bubbler line was charged with N-benzylbenzimidazole (208.1 mg, 1.0 mmol), Pd/C (10 wt %, dry powder, reduced) (20 mg) and THF (5 mL). The mixture was treated at rt with triethylsilane (320 µL, 2.0 mmol) and then stirred under nitrogen for 14 h at rt. The mixture was filtered through a 0.45 µM PTFE syringe filter and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (0 to 10% MeOH/ dichloromethane) to afford benzimidazole as a colorless solid (117.6 mg, 0.996 mmol 99%). The reactions generally exhibit an induction period of 5 to 30 min as indicated by the initiation of gas release (i.e., bubbling) from the reaction mixture. The use of Pd/C on a dry matrix is imperative as wet Pd/C results in decreased yield or no reaction.
Reference： [1]Haddach, Aubrey A.; Kelleman, Audrey; Deaton-Rewolinski, Melissa V. [Tetrahedron Letters, 2002, vol. 43, # 3, p. 399 - 402]
[2]Graham, Thomas H. [Tetrahedron Letters, 2015, vol. 56, # 21, p. 2688 - 2690]
  • 2
  • [ 670-96-2 ]
  • [ 100-39-0 ]
  • [ 37734-89-7 ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 2-Phenylimidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; 1.B To a mixture consisting of 2-phenylimidazole (TCI America, 3.0 g, 21 mmol) and N,N-dimethylformamide (40 mL) was added 60% sodium hydride in mineral oil (0.92 g, 23 mmol). After stirring for one hour at room temperature, a solution consisting of benzyl bromide (Aldrich, 2.73 mL, 22.9 mmol) in N,N-dimethylformamide (5 mL) was added dropwise while stirring. After stirring at room temperatures for 12 hours the reaction was complete as observed by TLC. The reaction mixture was partitioned between ethyl acetate (150 mL) and water (100 mL). The phases were separated and the organic layer was washed with brine (150 mL), and was subsequently dried over anhydrous magnesium sulfate. Concentration under reduced pressure afforded the crude product as an orange oil (4.2 g). The product was purified by flash silica column chromatography. Elution through a 80-g Silicycle flash silica cartridge with gradient of 5% to 30% ethyl acetate in hexanes afforded the title intermediate as a colorless oil (3.21 g, 66% yield). Rf 0.65 with 9:1 v/v dichloromethane-methanol; 1H-NMR (400 MHz; CDCl3) δ 7.57-7.53 (m, 2H), 7.42-7.28 (m, 6H), 7.19 (d, 1H), 7.11-7.07 (m, 2H), 6.97 (d, 1H), 5.22 (s, 2H).
Reference： [1]Current Patent Assignee: CAYMAN CHEMICAL COMPANY INC - US2010/75990, 2010, A1 Location in patent: Page/Page column 21
  • 3
  • [ 38696-20-7 ]
  • [ 37734-89-7 ]
  • [ 1217902-36-7 ]
YieldReaction ConditionsOperation in experiment
30% With potassium carbonate;trifuran-2-yl-phosphane; palladium diacetate; In N,N-dimethyl-formamide; at 140℃; for 16h;Inert atmosphere; To a mixture consisting of <strong>[38696-20-7]5-bromo-2-phenylpyrimidine</strong> (1.2 g, 5.1 mmol), palladium (II) acetate (Strem, 0.048 g, 0.21 mmol), tris(2-furyl)phosphine (TCI America, 0.098 g, 0.43 mmol) and potassium carbonate (1.17 g, 8.52 mmol) was added a solution consisting of 1-benzyl-2-phenyl-1H-imidazole (1.0 g, 4.3 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was brought to reflux at 140° C. (degrees Celsius) while under a N2 atmosphere. After stirring for 16 hours at reflux the solution was cooled to room temperature. The reaction mixture was partitioned between ethyl acetate (250 mL) and saturated aqueous ammonium chloride (100 mL). The phases were separated and the organic layer was washed with brine (150 mL), and was subsequently dried over anhydrous magnesium sulfate. Concentration under reduced pressure affords the crude product as an orange oil (0.658 g). The product was purified by flash silica column chromatography. Elution through a 80-g Silicycle.(R). flash silica cartridge with gradient of 5percent to 30percent ethyl acetate in hexanes afforded the title intermediate (0.495 g, 30percent yield); Rf 0.38 with 1:1 v/v ethyl acetate-hexane; 1H-NMR (400 MHz; CDCl3) delta 8.7 (s, 2H), 8.4 (m, 2H), 7.6 (m, 2H), 7.5-7.25 (m, 10H), 6.9 (m, 2H), 5.32 (s, 2H); MS (ESI+) m/z 389.2 (M+1); H-PGDS FPBA IC50: 15 muM.
Reference： [1]Patent: US2010/75990,2010,A1 .Location in patent: Page/Page column 21-22
  • 4
  • [ 4238-71-5 ]
  • [ 6969-90-0 ]
  • [ 37734-89-7 ]
YieldReaction ConditionsOperation in experiment
64% With potassium phosphate; bis(1,5-dicyclooctadiene)nickel; 1,2-bis-(dicyclohexylphosphino)ethane In tert-Amyl alcohol at 110℃;
Reference： [1]Muto, Kei; Hatakeyama, Taito; Yamaguchi, Junichiro; Itami, Kenichiro [Chemical Science, 2015, vol. 6, # 12, p. 6792 - 6798]
  • 5
  • [ 5306-98-9 ]
  • [ 37734-89-7 ]
  • 2'-(1-benzyl-1H-imidazol-2-yl)-4-methylbiphenyl-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1-methyl-2-phenyl-3-(diphenylphosphino)-1H-indole; potassium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; General procedure B (conditions B). General procedure: Two runs were set side by side. A Schlenck tube was loadedwith [RuCl2(p-cymene)]2 (7.7 mg, 0.0125 mmol, 2.5 mol%), L3 (9.8 mg, 0.025 mmol, 5 mol%),K2CO3 (173 mg, 1.25 mmol), The tube was backfilled with Ar (3 ×). Under light backflow of Ar, NMP (2.5 mL) was added, followed by the required substrate (1c-1e) (0.6 mmol), and p-chloroanisole (2a;62 L, 71 mg, 0.5 mmol). The tube was sealed and the reaction mixture was stirred at 140 °C for 24hours. After cooling to room temperature, the reaction mixtures from both tubes were combined in H2O(40 mL) and EtOAc (20 mL). The organic phase was separated and washed with H2O (3 × 30 mL),dried (MgSO4), filtered, and concentrated under reduced pressure. The monoarylated products (major)were isolated after flash chromatography.
Reference： [1]Li, You-Gui; Wang, Zhen-Yu; Zou, Ya-Ling; So, Chau-Ming; Kwong, Fuk-Yee; Qin, Hua-Li; Kantchev, Eric Assen B. [Synlett, 2017, vol. 28, # 4, p. 499 - 503]
  • 6
  • [ 57381-51-8 ]
  • [ 37734-89-7 ]
  • 2'-(1-benzyl-1H-imidazol-2-yl)-3-fluorobiphenyl-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; 1-methyl-2-phenyl-3-(diphenylphosphino)-1H-indole; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 140℃; for 24h;Schlenk technique; Inert atmosphere; Sealed tube; General procedure: Two runs were set side by side. A Schlenck tube was loadedwith [RuCl2(p-cymene)]2 (7.7 mg, 0.0125 mmol, 2.5 mol%), L3 (9.8 mg, 0.025 mmol, 5 mol%),K2CO3 (173 mg, 1.25 mmol), The tube was backfilled with Ar (3 ×). Under light backflow of Ar, NMP (2.5 mL) was added, followed by the required substrate (1c-1e) (0.6 mmol), and p-chloroanisole (2a;62 L, 71 mg, 0.5 mmol). The tube was sealed and the reaction mixture was stirred at 140 C for 24hours. After cooling to room temperature, the reaction mixtures from both tubes were combined in H2O(40 mL) and EtOAc (20 mL). The organic phase was separated and washed with H2O (3 × 30 mL),dried (MgSO4), filtered, and concentrated under reduced pressure. The monoarylated products (major)were isolated after flash chromatography.
Reference： [1]Synlett,2017,vol. 28,p. 499 - 503

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