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Chemistry
Heterocyclic Building Blocks
Imidazoles
Ethyl 1-(4-bromophenyl)-1H-imidazole-5-carboxylate
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Imidazoles
Aryls Bromides Esters

[ CAS No. 911641-38-8 ] {[proInfo.proName]}

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Chemical Structure| 911641-38-8
Chemical Structure| 911641-38-8
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Product Details of [ 911641-38-8 ]

CAS No. :911641-38-8 MDL No. :MFCD28404246
Formula : C12H11BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 295.13 Pubchem ID :-
Synonyms :

Safety of [ 911641-38-8 ]

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Precautionary Statements: UN#:
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Application In Synthesis of [ 911641-38-8 ]

* 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 [ 911641-38-8 ]

[ 911641-38-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1423706-19-7 ]
  • [ 36635-61-7 ]
  • [ 911641-38-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In ethanol at 65℃; for 4h; 1 Ethyl 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate To a solution of 4-bromoaniline (8.6 g, 50 mmol) in MeOH (100 mL) was added ethyl glyoxalate (12 mL, 60 mmol, 50% in toluene) and the resulting mixture heated at reflux for 3.5 h. The mixture was then concentrated in vacuo and the resulting residue reconstituted in anhydrous ethanol (100 mL) and treated with tosylmethyl isocyanide (14.6 g, 75 mmol) and potassium carbonate (13.8 g, 100 mmol). The resulting mixture was heated at 65° C. for 4 h, then cooled to rt and poured to water (500 mL) and the resulting solid collected by filtration. The crude material thus isolated was crystallized from ethyl acetate/hexane to give pure 3-(4-bromophenyl)-3H-imidazole-4-carboxylic acid ethyl ester (4). MS (ES+): m/z 295/297 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=1.27 (t, J=7.1 Hz, 3H), 4.22 (q, J=7.1 Hz, 2H), 7.22 (d, J=8.7 Hz, 2H), 7.61 (d, J=8.7 Hz, 2H), 7.65 (d, J=0.9 Hz, 1H) and 7.85 (d, J=0.9 Hz, 1H).
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2006/223799, 2006, A1 Location in patent: Page/Page column 9-10
  • 2
  • [ 911641-38-8 ]
  • [ 911641-39-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl 1-(4-bromophenyl)-1H-imidazole-5-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at -40 - -20℃; for 1h; Stage #2: With water; ammonium chloride In tetrahydrofuran at -20℃; 1 Ethyl 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate To a solution of 3-(4-bromophenyl)-3H-imidazole-4-carboxylic acid ethyl ester (4) (590 mg, 2.0 mmol) in dry THF was added lithium aluminium hydride (2.4 mL, 2.4 mmol, 1.0M in THF) dropwise at -40° C. under nitrogen, and the resulting mixture slowly warmed to -20° C. over 1 h. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution (3 mL) at -20° C. and diluted with ethyl acetate (40 mL). The suspension was filtered and the filtrate was washed with brine (20 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to afford [3-(4-bromophenyl)-3H-imidazol-4-yl]-methanol (5). MS (ES+): m/z 253/255 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=2.25 (br s, 1H), 4.56 (s, 2H), 7.14 (s, 1H), 7.40 (d, J=8.8 Hz, 2H), 7.63 (s, 1H), 7.64 (d, J=8.8 Hz, 2H).
Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US2006/223799, 2006, A1 Location in patent: Page/Page column 9-10
  • 3
  • [ 36635-61-7 ]
  • [ 2521-92-8 ]
  • [ 911641-38-8 ]
YieldReaction ConditionsOperation in experiment
51% With bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; potassium carbonate In N,N-dimethyl-formamide Schlenk technique; Irradiation;
Reference： [1]Deng, Qiao-Hui; Zou, You-Quan; Lu, Liang-Qiu; Tang, Zi-Long; Chen, Jia-Rong; Xiao, Wen-Jing [Chemistry - An Asian Journal, 2014, vol. 9, # 9, p. 2432 - 2435]

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