Alternatived Products of [ 13278-38-1 ]
Product Details of [ 13278-38-1 ]
CAS No. : | 13278-38-1 |
MDL No. : | |
Formula : |
C13H10BrNO2
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
292.13
|
Pubchem ID : | - |
Synonyms : |
|
Safety of [ 13278-38-1 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 13278-38-1 ]
* 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 [ 13278-38-1 ]
- 1
-
[ 88-67-5 ]
-
[ 106-40-1 ]
-
[ 13278-38-1 ]
Yield | Reaction Conditions | Operation in experiment |
93% |
With potassium carbonate at 75℃; for 0.333333h; microwave irradiation; |
|
40% |
With copper(l) iodide; copper; potassium carbonate In N,N-dimethyl-formamide for 2h; Inert atmosphere; |
2-(4-Fluorophenylamino)benzoic acid (9a)
General procedure: To a solution of 7 (1.00 g, 4.03 mmol) in DMF (15 mL) was added K2CO3 (1.11 g, 8.08 mmol), CuI (38 mg, 0.02 mmol), Cu (26 mg, 0.04 mmol) and 8a (974 mg, 0.61 mmol). The resulting solution was heated to 130 °C under N2 for 2 h. After filtration through celite, the filtrate was diluted with EtOAc (150mL × 1) and washed with distd H2O (450 mL × 5). The organic layer was dried over Na2SO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography (MeOH: CH2Cl2 = 0:100 - 2: 98) to give 9a (766 mg, 83%) as a solid. |
|
With copper diacetate; sodium acetate In water Reflux; |
|
|
With 4-methyl-morpholine; copper(I) oxide In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; |
|
|
With copper; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 20h; Schlenk technique; Inert atmosphere; |
4.3 General procedure for the preparation of compounds
General procedure: A mixture of K2CO3 (1.0mmol, 1.0 eq), amine (1.2mmol, 1.2 eq), ortho-iodo benzoic acid (1.0mmol, 1.0 eq) and DMF (2.0mL) and copper powder (0.001mmol, 0.1% eq) were stirred in the schlenk tube for 12h at 100°C under argon condition, and stopped heat and cooled to 25°C. The solid (bottle green) was diluted with water, acidified with 2.0N HCl until pH 2 was adjusted. The black solid was precipitated and filtered. The filter cake was washed with an excess of water to remove the excess amine, dissolved in dichloromethane. The dichloromethan was concentrated by rotary evaporation under reduced pressure and dried over Na2SO4. The crude compounds, o-aminobenzoic acid derivatives, were obtained. Then o-aminobenzoic acid derivatives (1.0 eq), tryptamine (1.0 eq), EDCI·HCl (1.2 eq), HOBT (1.1 eq) were dissolved in dichloromethane (3mL), and Et3N (2.5 eq) was added at room temperature and stirred for 8h. After completion of the reaction detected by TLC, the reaction liquid was concentrated by rotary evaporation under reduced pressure. Then the resulting residue was purified by silica gel flash column chromatography to afford the desired product as a solid and the total yield was 49-95%. |
|
With copper; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 8h; |
|
Reference:
[1]Maradolla, Mohan Babu; Mandha, Amaravathi; Garimella, Chandra Mouli
[Journal of Chemical Research, 2007, # 10, p. 587 - 589]
[2]Chen, Chun-Yung; Chen, Liang-Chieh; Chen, Yi-Ying; Chu, Jung-Chun; Hsu, Kai-Cheng; Huang, Wei-Jan; Lin, Mei-Hsiang; Lin, Tony Eight; Pan, Shiow-Lin; Shiao, Young-Ji; Su, Chih-Jou; Tseng, Hui-Ju; Wang, Chen-Yu; Yang, Ying-Chen
[European Journal of Medicinal Chemistry, 2020, vol. 192]
[3]Li, Xi-An; Wang, Hong-Li; Yang, Shang-Dong
[Organic Letters, 2013, vol. 15, # 8, p. 1794 - 1797]
[4]Zheng, Zisheng; Dian, Longyang; Yuan, Yucheng; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang
[Journal of Organic Chemistry, 2014, vol. 79, # 16, p. 7451 - 7458]
[5]Fan, Xiaohong; Li, Junfang; Long, Lin; Shi, Tao; Liu, Dan; Tan, Wen; Zhang, Honghua; Wu, Xiaoyan; Lei, Xiaoyong; Wang, Zhen
[European Journal of Medicinal Chemistry, 2021, vol. 222]
[6]Hao, Xiangyong; Deng, Jiedan; Zhang, Honghua; Liang, Ziyi; Lei, Fang; Wang, Yuqing; Yang, Xiaoyan; Wang, Zhen
[Bioorganic and Medicinal Chemistry, 2022, vol. 55]