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[ CAS No. 16265-11-5 ] {[proInfo.proName]}

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Chemical Structure| 16265-11-5
Chemical Structure| 16265-11-5
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Product Details of [ 16265-11-5 ]

CAS No. :16265-11-5 MDL No. :MFCD03411959
Formula : C4H5BrN2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :APLZLUYWLINBOZ-UHFFFAOYSA-N
M.W : 161.00 Pubchem ID :2773267
Synonyms :

Safety of [ 16265-11-5 ]

Signal Word:Warning Class:
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16265-11-5 ]

* 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 [ 16265-11-5 ]

[ 16265-11-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 16265-11-5 ]
  • [ 80-48-8 ]
  • [ 24134-09-6 ]
  • 2
  • [ 16265-11-5 ]
  • [ 74-88-4 ]
  • [ 24134-09-6 ]
  • [ 850429-59-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; To a solution of 4-bromo-2-methyl-1 H-imidazole (2 g, 12.42 mmol) in N, N- dimethylformamide (10 ml.) was added potassium carbonate (3.78 g, 27.3 mmol) followed by methyl iodide (0.928 ml_, 14.91 mmol). The reaction mixture was stirred at room temperature overnight and then partitioned between dichloromethane and water and the layers separated. The aqueous layer was extracted with dichloromethane (x2) and the organic layers were combined and concentrated, azeotroping with toluene to give a mixture of the title compounds. 1H NMR delta (MeOH-d4): Major isomer: 2.31 (3H, s), 3.58 (3H, s), 6.97 (1 H, s). Minor isomer: 2.38 (3H, s), 3.55 (3H, s), 6.82 (1 H, s).
  • 3
  • [ 882679-40-5 ]
  • [ 16265-11-5 ]
  • [ 1533440-46-8 ]
YieldReaction ConditionsOperation in experiment
65% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; at 90℃; for 18h;Inert atmosphere; Compound 7.1. Methyl 4-methyl-3-(2-methyl-lH-imidazol-5-yl)benzoate. To a solution of methyl 4-methyl-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 600 mg, 2.17 mmol) in dioxane (20 mL) was added 2-methyl-4-bromo imidazole (419 mg, 2.6 mmol), Pd(dppi)Cl2*CH2Cl2 (180 mg, 0.22 mmol). The mixture was degassed argon and stirred for 10 minutes then aqueous potassium carbonate (1M, 10 mL, 10 mmol) was added and the mixture was stirred at 90 C for 18 h. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and filtered through Celite. The organic phase was washed by brine, dried (MgSC>4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-5 % MeOH in EtOAc) to yield the title compound as a foam (324 mg, 65%). m/z (ES+) 231 (M+H)+. NMR (400 MHz, CDC13) delta 8.30 (br s, 1H), 7.86 (dd, J= 7.9, 1.9 Hz, 1H), 7.32 (d, J= 7.9 Hz, 1
  • 4
  • [ 882679-40-5 ]
  • [ 16265-11-5 ]
  • [ 1533440-46-8 ]
YieldReaction ConditionsOperation in experiment
65% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 18h;Inert atmosphere; Compound 7.1. Methyl 4-methyl-3-(2-methyl-lH-imidazol-5-yl)benzoate. To a solution of methyl 4-methyl-3-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 600 mg, 2.17 mmol) in dioxane (20 mL) was added 2-methyl-4-bromo imidazole (419 mg, 2.6 mmol), Pd(dppf)Cl2 CH2Cl2 (180 mg, 0.22 mmol). The mixture was degassed argon and stirred for 10 minutes then aqueous potassium carbonate (1M, 10 mL, 10 mmol) was added and the mixture was stirred at 90 C for 18 h. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and filtered through Celite. The organic phase was washed by brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-5 % MeOH in EtOAc) to yield the title compound as a foam (324 mg, 65%). m/z (ES+) 231 (M+H)+. NMR (400 MHz, CDC13) delta 8.30 (br s, 1H), 7.86 (dd, J= 7.9, 1.9 Hz, 1H), 7.32 (d, J= 7.9 Hz, 1H), 7.08 (s, 1H), 3.92 (s, 3H), 2.53 (s, 3H), 2.51 (s, 3H)
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