Alternatived Products of [ 5851-44-5 ]
Product Details of [ 5851-44-5 ]
CAS No. : | 5851-44-5 |
MDL No. : | MFCD00714456 |
Formula : |
C11H14N2
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
174.24
|
Pubchem ID : | - |
Synonyms : |
|
Safety of [ 5851-44-5 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 5851-44-5 ]
* 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 [ 5851-44-5 ]
- 1
-
[ 5851-44-5 ]
-
[ 74733-28-1 ]
-
[ 133052-57-0 ]
- 2
-
[ 5851-44-5 ]
-
[ 74733-27-0 ]
-
4-(2-Butyl-benzoimidazol-1-ylmethyl)-2-methoxy-benzoic acid methyl ester
[ No CAS ]
- 3
-
[ 5851-44-5 ]
-
[ 128577-48-0 ]
-
[ 133052-53-6 ]
- 4
-
[ 5851-44-5 ]
-
[ 88089-94-5 ]
-
[ 133052-55-8 ]
- 5
-
[ 5851-44-5 ]
-
[ 589-15-1 ]
-
[ 1247725-67-2 ]
Yield | Reaction Conditions | Operation in experiment |
71% |
With Cs2CO3 In N,N-dimethyl-formamide at 120℃; Microwave irradiation; Inert atmosphere; |
5.1.2 General procedure for N-alkylation of heterocycles (6a-6r)
General procedure: The corresponding heterocycle (1.0mmol, 1 equiv.), 4-bromobenzyl bromide (1.2mmol, 1.2 equiv.) and cesium carbonate (2mmol, 2 equiv.) in N,N’-dimethylformamide (5.0M) was stirred at 120°C under microwave irradiation for 30min. The reaction was quenched with water (50mL), extracted with ethyl acetate (2×50mL). The combined organic layers were washed with water (30mL), brine (25mL) and dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by FCC (0-5% MeOH in CH2Cl2) to afford the N-alkylated heterocycles in 52-79% yield. |
71% |
With Cs2CO3 In N,N-dimethyl-formamide at 120℃; Microwave irradiation; Inert atmosphere; |
5.1.2 General procedure for N-alkylation of heterocycles (6a-6r)
General procedure: The corresponding heterocycle (1.0mmol, 1 equiv.), 4-bromobenzyl bromide (1.2mmol, 1.2 equiv.) and cesium carbonate (2mmol, 2 equiv.) in N,N’-dimethylformamide (5.0M) was stirred at 120°C under microwave irradiation for 30min. The reaction was quenched with water (50mL), extracted with ethyl acetate (2×50mL). The combined organic layers were washed with water (30mL), brine (25mL) and dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by FCC (0-5% MeOH in CH2Cl2) to afford the N-alkylated heterocycles in 52-79% yield. |
|
Stage #1: 2-butyl-1H-benzimidazol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h;
Stage #2: 1-bromo-4-(bromomethyl)benzene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 5h; |
4.1.7. General procedure for the preparation of 1-(4-bromo-benzyl)-benzimidazole (14a-14l)
General procedure: NaH (0.48 g, 60% in mineral oil, 12.0 mmol) was added in batches to a solution of 13 in DMF (10 mL) at 0 °C, and the mixture was stirred for 15 min. A solution of 1-bromo-4-(bromomethyl)benzene (1.0 g, 4.0 mmol) in DMF (5 mL) was then added and the mixture was stirred for 5 h at room temperature. The mixture was poured into cold saturated NaCl solution, filtered, and the filter cake was recrystallized with 95% alcohol to give 14a-14l as white solid in yields of 45-65%. |
Reference:
[1]Gising, Johan; Gopalan, Greeshma; Hallberg, Mathias; Larhed, Mats; Petersen, Nadia N.; Roy, Tamal
[Bioorganic and Medicinal Chemistry, 2022, vol. 66]
[2]Gising, Johan; Gopalan, Greeshma; Hallberg, Mathias; Larhed, Mats; Petersen, Nadia N.; Roy, Tamal
[Bioorganic and Medicinal Chemistry, 2022, vol. 66]
[3]Location in patent: experimental part
Bai, Renren; Wei, Zhen; Liu, Jie; Xie, Weijia; Yao, Hequan; Wu, Xiaoming; Jiang, Jieyun; Wang, Qiujuan; Xu, Jinyi
[Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 15, p. 4661 - 4667]
- 6
-
[ 5851-44-5 ]
-
[ 944-33-2 ]
-
[ 1560633-48-8 ]
Yield | Reaction Conditions | Operation in experiment |
67% |
With sodium acetate In tetrahydrofuran at 20℃; for 24h; |
|
Reference:
[1]Zubriene, Asta; Capkauskaite, Edita; Gylyte, Joana; Kisonaite, Migle; Tumkevicius, Sigitas; Matulis, Daumantas
[Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 1, p. 124 - 131]