Category: 13273-53-5

Adding a certain compound to certain chemical reactions, such as: 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, belongs to triazoles compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13273-53-5, category: Triazoles

Intermediate 602: 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole Compound 601 (0.6 g, 3.69 mmol) was dissolved in 15 ml of 1,4-dioxane, added with 1.125 g (4.43 mmol) of bis(pinacolato)diboron, 1.086 g (11.07 mmol) of potassium acetate, and 0.3 g (0.37 mmol) of [1,1-bis(di-phenylphosphino)ferrocene]palladium chloride dichloromethane complex under the protection of nitrogen, heated to 95 C, reacted for 5 h, and then cooled to room temperature. 50 mL of water was added and stirred for 30 min, and filtered to afford 0.35 g of solid. Yield: 45.39%.

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Reference:
Patent; Beijing Forelandpharma Co. Ltd.; ZHANG, Xingmin; JI, Qi; WANG, Lei; GAO, Congmin; WANG, Ensi; DU, Zhenjian; GONG, Longlong; CHEN, Bo; (137 pag.)EP3072893; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 13273-53-5,Some common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 2-((4-chlorophenethyl)amino)-2-phenyl-l-(6-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-lH-indol-3-yl)ethan-l-one (0.06 g, 0.11 mmol), 4-bromo-l -methyl – 1H- 1,2, 3 -triazole (0.019 g, 0.11 mmol), and cesium carbonate (0.095 g, 0.29 mmol) in a mixture of 4:1 dioxane:water (5 ml) was degassed for 20 minutes with argon. S-Phos Pd precatalyst G3 (0.009 g, 0.01 mmol) was added and degassing was continued for another 10 minutes. The reaction mixture was heated in a sealed tube with microwave heating at 135 C for 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was treated with water (15 ml) and extracted with ethyl acetate (2 x 15 ml). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the title compound as solid (0.040 g, 74%) in racemic form.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methyl-1H-1,2,3-triazole, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMCEUTICALS, INC.; WILSON, Jonathan, E.; LEVELL, Julian, R.; (152 pag.)WO2019/161157; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 13273-53-5, These common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of the crude (S)-4-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide (30 mg, 0.059 mmol) in residual dioxane was added 4-bromo-1-methyl-1H-1,2,3-triazole (14.24 mg, 0.088 mmol), PdCl2(dppf) (42.9 mg, 0.059 mmol), DME (195 mul) and 2 M Na2CO3 (130 mul) at room temperature. The reaction mixture was stirred for 5 h. After water and EtOAc were added, the organic layer was extracted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered off, and concentrated in vacuo. The crude product was purified by prep HPLC. The pure fractions were lyophilized yielding (S)-4-(2-amino-5-(1-methyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-N-(1-(3-chlorophenyl)-2-hydroxyethyl)-2-fluorobenzamide as a TFA salt (25% over 2 steps). LCMS (m/z): 467.3 (MH+), 0.61 min; 1H NMR (400 MHz, CD3OD) delta ppm 8.64 (m, 1H), 8.31 (m, 1H), 8.25 (m, 2H), 8.2 (m, 1H), 7.82 (m, 1H), 7.4 (m, 3H), 7.28 (m, 2H), 7.22 (m, 1H), 5.11 (m, 1H), 4.07 (s, 3H), 3.78 (m, 2H).

The synthetic route of 13273-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 13273-53-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 13273-53-5 as follows.

General procedure: To a 50 mL round bottle flask was added 1,1?-Bis(diphenylphosphino)ferrocenedichloro Palladium(II) (0.1equiv), bromide (1.0equiv) and vinylboronic acid pinacol ester (2.0equiv) in 20mL dioxane. The mixture was degassed for 5min, and sodium carbonate aqueous solution (2.0M, 10equiv) was added. The mixture was then heated to 85C for 14h. After cooled to rt, the reaction mixture was filtered through a short Celite pad and washed with EtOAc. The organic solution was concentrated under reduced pressure and the residue was loaded into combi flush for purification to afford the product as oil.

According to the analysis of related databases, 13273-53-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lian, Yajing; Burford, Kristen; Londregan, Allyn T.; Tetrahedron; vol. 71; 50; (2015); p. 9509 – 9514;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 13273-53-5,Some common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of 6-1 (50 mg, 0.13 mmol, 1.0 eq) and 6-la (28 mg, 0.17 mmol, 1.30 eq) in dioxane (2 mL) and H20 (0.5 mL) was added Na2C03 (38 mg, 0.36 mmol, 2.7 eq) and Pd(dppf)Cl2 (10 mg, 13 umol, 0.1 eq) in one portion under N2. The mixture was stirred at 100 C for 16 h. LCMS showed the starting material was consumed completely and one peak with desired MS was detected. The reaction mixture was concentrated under reduced pressure to remove solvent, and then added CH3CN (5 mL), filtered to give a black-brown liquid. The residue was purified by prep-HPLC. LCMS and XH NMR confirmed Compound 6 was obtained (2.06 mg, 5.5 umol, 4.2% yield, HC1). LCMS (ESI): RT = 0.752 min, mass calcd. For Ci6H22N402S, 334.15 m/z found 334.9[M+H]+.1H NMR (400MHz, DMSO-c) 58.76 (s, 1H), 8.34 (br s, 1H), 7.95 (d, J=2.00 Hz, 1H), 7.60 (dd, J=8.80, 2.00 Hz, 1H), 6.91 (d, J=8.80 Hz, 1H), 4.13 (s, 3H), 3.11 (s, 3H), 2.60 – 2.53 (m, 1H), 2.02 – 1.89 (m, 2H), 1.74 – 1.63 (m, 2H), 1.62 – 1.51 (m, 1H), 1.49 – 1.26 (m, 5H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methyl-1H-1,2,3-triazole, its application will become more common.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 13273-53-5

Step 5 To the above solution was added 4-bromo-1-methyl-1H-1,2,3-triazole (XXXII) (0.064 g, 0.395 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (0.032 g, 0.040 mmol) and 2 M aqueous solution of potassium carbonate (0.395 mL, 0.790 mmol). The reaction mixture was heated overnight at 95 C. The reaction mixture was absorbed on silica and purified by ISCO using CHCl3/7N NH3 in MeOH (0?5%) followed by preparative TLC to obtain N-(6-(1-methyl-1H-1,2,3-triazol-4-yl)isoquinolin-3-yl)-1-(3,3,3-trifluoropropyl) piperidine-4-carboxamide (271) as a beige solid (0.011 g, 0.025 mmol, 6.44% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.60-1.73 (m, 2H), 1.76-1.84 (m, 2H), 1.92-2.01 (m, 2H), 2.41-2.60 (m, 5H), 2.94 (br d, J=11.25 Hz, 2 H), 4.14 (s, 3H), 8.01 (dd, J=8.51, 1.37 Hz, 1H), 8.11 (d, J=8.51 Hz, 1H), 8.28 (s, 1H), 8.50 (s, 1H), 8.73 (s, 1H), 9.11 (s, 1H), 10.55 (s, 1H); ESIMS found for C21H23F3N6O m/z 433.2 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13273-53-5, its application will become more common.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mittapalli, Gopi Kumar; Hofilena, Brian Joseph; Marakovits, Joseph Timothy; Chiruta, Chandramouli; Mak, Chi Ching; Cao, Jianguo; (324 pag.)US2017/313681; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromo-1-methyl-1H-1,2,3-triazole

The crude was dissolved in 10ml of tetrahydrofuran /1.5mlDMF added potassium carbonate (1.14g, 8.30mmol), methyl iodide (471mg, 3.32mmol), 20 ~ 30 for 48 hours, 20ml of water and 20ml of ethyl acetate, layered aqueous layer was adjusted with hydrochloric acid, pH = 1-5, and extracted with 20ml of ethyl acetate, 40 concentrated under reduced pressure to 3ml, was cooled to 0 crystallization, filtration, 40 dried in vacuo to give 1-methyl -1H-1, 2,3-triazole-4-carboxylate 587mg, 50% yield.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; The Haiya Chemical Co., Ltd.; Jiang, Yueheng; Que, Limin; Xu, Jun; Qin, Dongguang; Cai, Tong; (17 pag.)CN105585534; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 13273-53-5, A common heterocyclic compound, 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, molecular formula is C3H4BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1. (S)-(6-bromo-5-(2,5-difluoro-4-nitrophenoxy)-2-methyl-3,4-dihydroquinoliii-l(2H)- yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(4,5-difluoro-2-nitrophenoxy)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone [0568] A 100-mL, 3-necked round-bottom flask was charged with a solution of (S)-(6-bromo-5- hydroxy-2-methyl-3,4-dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone (2.00 g, 6.45 mmol) in tetrahydrofuran (20 mL). Potassium tert-butoxide (0.797 g, 7.10 mmol) was added in portions at 0 C and the mixture stirred for 5 minutes. 1 ,2,4-Trifluoro-5-nitrobenzene (1.72 g, 9.71 mmol) was then added, and the resulting mixture stirred at 0 C for 3 h. Hydrochloric acid (I aqueous, 10 mL) was added, and the aqueous phase was separated and extracted with ethyl acetate (2 x 15 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 : 10, ethyl acetate/petroleum ether) to afford a mixture of (S)-(6-bromo-5-(2,5-difluoro-4-nitrophenoxy)-2- methyl-3,4-dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(4,5-difluoro-2- nitrophenoxy)-2-methyl-3,4-dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone (2.1 g, 70%) as yellow oil. MS (ESI, pos. ion) m/z 467,469[M+H]+ Step 2. (S)-(5-(4-amino-2,5-difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinoliii-l(2H)- yl)(cyclopropyl)methanone and (S)-(5-(2-amino-4,5-difluorophenoxy)-6-bromo-2-methyl-3,4- dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone [0569] A 100-mL, round-bottom flask was charged with a mixture of (S)-(6-bromo-5-(2,5-difiuoro- 4-nitrophenoxy)-2-methyl-3,4-dihydroquinolin- 1 (2H)-yl)(cyclopropyl)methanone and (S)-(6- bromo-5-(4,5-difiuoro-2-nitrophenoxy)-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone (2.1 g, 4.49 mmol), iron powder (1.26 g, 22.5 mmol), ammonium chloride (0.476 g, 8.90 mmol), tetrahydrofuran (10 mL), ethanol (10 mL), and water (3 mL). The resulting mixture stirred overnight at 80 C. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was extracted with ethyl acetate (2 x 15 mL). The combined organic layers were concentrated under vacuum to afford a mixture of (S)-(5-(4-amino-2,5- difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinolin- 1 (2H)-yl)(cyclopropyl)methanone and (S)-(5-(2-amino-4,5-difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone (1.8 g, 96%) as brown oil, which was directly used in next step without further purification. MS (ESI, pos. ion) m/z 437,439[M+H]+ Step 3. (S)-(6-bromo-5-(3,4-difluorophenoxy)-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(2,5-difluorophenoxy)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone [0570] A 100-mL, round-bottom flask was charged with a mixture of (S)-(5-(2-amino-4,5- difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinolin- 1 (2H)-yl)(cyclopropyl)methanone and (S)-(5-(4-amino-2,5-difluorophenoxy)-6-bromo-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone (1.8 g, 4.12 mmol) and N,N-dimethylformamide (10 mL). A solution of tert-butyl nitrite (1.2 g, 11.64 mmol) in N,N-dimethylformamide (10 mL) was added dropwise, and the resulting solution stirred for 4 h at 50 C. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (100 mL). The organic layer was washed with water (3 x 20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 : 10, ethyl acetate/petroleum ether) to afford a mixture of (S)-(6-bromo-5-(3,4-difluorophenoxy)-2-methyl-3,4- dihydroquinolin- 1 (2H)-yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(2,5-difluorophenoxy)-2- methyl-3,4-dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone (0.600 g, 35%) as yellow oil. MS (ESI, pos. ion) m/z 422,424[M+H]+. Step 2. (S)-cyclopropyl(5-(3,4-difluorophenoxy)-2-methyl-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-3,4-dihydroquinolin-l(2H)-yl)methanone and (S)-cyclopropyl(5-(2,5- difluorophenoxy)-2-methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroquinolin-l(2H)-yl)methanone [0666] A mixture of (S)-(6-bromo-5-(3,4-difluorophenoxy)-2-methyl-3,4-dihydroquinolin-l(2H)- yl)(cyclopropyl)methanone and (S)-(6-bromo-5-(2,5-difiuorophenoxy)-2-methyl-3,4- dihydroquinolin-l(2H)-yl)(cyclopropyl)methanone (0.100 g, 0.24 mmol), bis(pinacolato)diboron (0.600 g, 2.37 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.019 g, 0.02 mmol), and potassium acetate (0.046 mg, 0.47 mmol) in 1,4-dioxane (10 mL) was stirred overnight at 80 C. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by p…

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., category: Triazoles

Step 2. (S)-cyclopropyl(5-(2-fluorophenoxy)-2-methyl-6-(l-methyl-lH-l,2,3-triazol-4-yl)-3,4- dihydroquinolin-l(2H)-yl)methanone [0670] A mixture of (S)-cyclopropyl(5-(2-fluorophenoxy)-2-methyl-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-3,4-dihydroquinolin-l(2H)-yl)methanone (0.140 g, 0.31 mmol), 4-bromo-l- methyl-lH- 1,2, 3-triazole (0.050 g, 0.31 mmol), sodium carbonate (0.090 g, 0.85 mmol), and [1,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.010 g, 0.01 mmol) in 1,4-dioxane (10 mL) and water (3 mL) was stirred overnight at 80 C. The reaction mixture was cooled to room temperature, filtered through a short pad of Celite, and concentrated under vacuum. The residue was purified via preparative thin layer chromatography (eluting with 2: 1, petroleum ether-ethyl acetate). The product was further purified by preparative-HPLC with the following conditions (Waters I) : Column, XBridge CI 8, 19×150 mm, 5um; Mobile Phase water (0.05% ammonium bicarbonate) and acetonitrile (35% to 65% acetonitrile in 10 min, flow rate: 20 mL/min); Detector: UV254&220 nm. This afforded (S)-cyclopropyl(5-(2-fluorophenoxy)-2-methyl- 6-(l -methyl- lH-l,2,3-triazol-4-yl)-3,4-dihydroquinolin-l(2H)-yl)methanone (0.033 g, 26%) as a white solid. 1H NMR (400 MHz, CD3OD) delta ppm 0.74-0.81 (m, 1 H), 0.89-1.03 (m, 2 H), 1.1 1-1.21 (m, 4 H), 1.35-1.47 (m, 1 H), 1.95-2.05 (m, 1 H), 2.17-2.40 (m, 2 H), 2.65-2.78 (m, 1 H), 4.07 (s, 3 H), 4.75-4.81 (m, 1 H),6.40-6.49 (m, 1 H), 6.89-6.97 (m, 2 H), 7.21-7.27 (m, 1 H), 7.51 (d, J=8.40Hz, 1 H), 8.03 (s, 1 H), 8.08 (d, J=8.40 Hz, 1 H). MS (ESI, pos. ion) m/z 407[M+H]+.

According to the analysis of related databases, 13273-53-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H4BrN3

Step 2. (S)-2-(l-(cyclopropanecarbonyl)-2-methyl-6-(l-methyl-lH-l,2,3-triazol-4-yl)-l,2,3,4- tetrahydroquinolin-5-yloxy)benzonitrile [0440] A mixture of (S)-2-(l-(cyclopropanecarbonyl)-2-methyl-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l,2,3,4-tetrahydroquinolin-5-yloxy)benzonitrile (0.050 g, 0.1 1 mmol), 4-bromo- 1 -methyl- lH-l ,2,3-triazole (0.025 g, 0.15 mmol), cesium carbonate (0.110 g, 0.34 mmol), [Iota, – bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.10 g, 0.01 mmol) in l ,4-dioxane(10 mL) and water (3 mL) was stirred overnight at 80 C. The reaction mixture was cooled to room temperature and filtered through a short pad of Celite. The filtrate was concentrated and purified via preparative thin layer chromatography (eluting with 25% ethyl acetate-petroleum ether) to afford (S)-2-(l-(cyclopropanecarbonyl)-2-methyl-6-(l-methyl-lH-l ,2,3-triazol-4-yl)- l,2,3,4-tetrahydroquinolin-5-yloxy)benzonitrile (0.006 g, 13%) as a white solid. MS (ESI, pos. ion) m/z 414[M+H]+. 1H NMR(400 MHz, CD3OD) delta ppm 0.75-0.82(m, 1H), 0.88-1.05(m, 2H), 1.15- 1.25(m, 3H), 1.28-1.35(m, 1H), 1.45-1.55(m, 1H), 1.97-2.05(m, 1H), 2.15-2.25(m, 1H), 2.27- 2.45(m, 1H), 2.60-2.75(m, 1H), 4.09(s, 3H), 4.75-4.85(m, 1H), 6.58(d, J=8.40 Hz, 1H), 7.17(t, J=8.00 Hz, 1H), 7.45-7.51(m, 1H), 7.57(d, J=8.40 Hz, 1H), 7.78(d, J=1.20 Hz, 1H), 8.03-8.07(m, 2H). MS (ESI, pos. ion) m/z 414[M+H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 13273-53-5.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics