Category: 288-36-8

Electric Literature of 288-36-8,Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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.

Intermediate 52: 3-Fluoro-2-(2H-1 ,2,3-triazol-2-yl)benzoic acid.Step A: 3-Fluoro-2-(2H-1 ,2,3-triazol-2-yl)benzonitrile and 3-fluoro-2-(1 H- 1 ,2,3-triazol-1 -yl)benzonitrile. A mixture of 2,3-difluorobenzonitrile (4.0 g, 28.8 mmol), 2H-1 ,2,3-triazole (1 .9 g, 28.8 mmol) in DMF (85.0 mL) and K2C03 (7.9 g, 57.5 mmol) were heated to 125 C for 1 .5 h. After cooling to rt, water was added and the mixture extracted with EtOAc (2 X). The combined organics were washed with brine and dried (Na2S04). Purification via FCC (10-100% EtOAc in hexanes) gave two products. 3-Fluoro-2-(2H-1 ,2,3-triazol-2- yl)benzonitrile (1 .6 g, 29%), 1H NMR (CDCI3): 7.99 (s, J = 6.6 Hz, 2H), 7.67 – 7.63 (m, 1 H), 7.61 – 7.53 (m, 2H), 7.26 (s, 6 H) and 3-fluoro-2-(1 H-1 ,2,3-triazol- 1 -yl)benzonitrile (2.0 g, 38%) 1H NMR (CDCI3): 7.97 (dd, J = 4.4, 2.8 Hz, 1 H), 7.95 (d, J = 1 .2 Hz, 1 H), 7.70 (tt, J = 5.7, 2.8 Hz, 1 H), 7.65 (td, J = 8.1 , 4.9 Hz, 1 H), 7.62 – 7.57 (m, 1 H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 288-36-8

To a mixture of the product from Step 2 (7.9 g, 38 mmol) , Cs2CO3 (24.8 g, 76 mmol) , and CuI (2.88 g, 7.6 mmol) in DMF (200 mL) was added 2H- [1, 2, 3] triazole (5.24 g, 76 mmol) and N,N’-dimethyl-cyclohexane-1, 2-diamine (0.9 g, 6.5 mmol) and the mixture was stirred at 110 overnight. The cooled mixture was adjusted topH 12 with 1 N sodium hydroxide and extracted with EtOAc (50 mL x 3) . The aqueous layer was adjusted topH 4 with 1 N HCl and extracted with EtOAc (50 mLx4) . The extracts were dried over Na2SO4, filtered, the filtrate concentrated in vacuo, and the residue was purified by silica gel column chromatography (petroleum ether: EtOAc10: 1) to provide the title compound. LRMS m/z (M+H) 196.0 found, 196.0 required.

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 288-36-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; (59 pag.)WO2016/101118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 288-36-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 288-36-8 name is 1H-1,2,3-Triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a stirred solution of 1,2, 3-triazole (2.0 g, 28.9 mmol) in THF (10 mL) was added NaH (l.065g, 43.1 mmol) portion wise at 0 C under inert atmosphere. After being stirred for 45 min at 0C, 2-(trimethylsilyl)ethoxymethyl-Cl (SEM-C1; 7.6 mL, 43.1 mmol) was added to the reaction mixture. After completion of addition the reaction mixture was allowed to warm to RT and stirred for 12 h. The reaction mixture was quenched with water and extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to give crude compound. The crude material was purified by column chromatography eluting with 10% EtO Ac/hexane to afford N-2-(trimethylsilyl)ethoxymethyl- 1,2, 3-triazole (3.5 g, 17.5 mmol, 61%) as a liquid. Mass: m/z 200 [M++l].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-1,2,3-Triazole, and friends who are interested can also refer to it.

Reference:
Patent; INNOCRIN PHARMACEUTICALS, INC.; EISNER, Joel; (88 pag.)WO2019/182743; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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. Recommanded Product: 1H-1,2,3-Triazole

Step A: 6-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile. To 3-bromo-5-methylpicolinonitrile (2.2 g, 11 mmol) in DMF (28 mL) was added K2CO3 (1.7 g, 12 mmol) and 2H-1,2,3-triazole (650 muL, 11 mmol). The mixture was heated to 100 C. for 36 h, cooled to rt and extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (10-100% EtOAc in hexanes) gave the title compound (1 g, 48%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-36-8, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Dvorak, Curt A.; Shireman, Brock T.; US2014/275095; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, 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 288-36-8 as follows.

Example 120: Preparation of 4,5-dibromo-lH-pi,2,31triazoleRr Br. BrN^ NH *” ‘ \V NVNH To a solution of IH-[1, 2,3]triazole (1.26 ml, 21.7 mmol) in water (10 ml) at 5tfC, was added bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at 5CPC for 1.5 hours. The white solid (2.375 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (1.83 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (375 mg) was isolated via filtration and washed with water (5ml). The white solids were combined and dried to give 4,5-dibromo- IH-[1, 2,3]- triazole (4.92 g, 93percent yield). M.p. 194.7C.

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA LIMITED; WO2007/96576; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 288-36-8, name is 1H-1,2,3-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C2H3N3

A solution of 5-bromo-2-chloro-6-methylnicotinonitrile (8.5 g, 36.7 mmol), 2H-1,2,3-triazole (5.07 g, 73.4 mmol) and potassium carbonate (15.2 g, 110.2 mmol) in acetonitrile (150 mL) was stirred at 40 C. overnight. The mixture was filtered and washed with ethyl acetate (200 mL*3). The filtrate was concentrated to afford a crude product. The crude product was purified by flash column chromatography over silica gel (eluent: petroleum ether/ethyl acetate from 100/0 to 30/70). The eluent was collected and the solvent was concentrated under reduced pressure to give the product as a yellow solid (7 g, 72% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 2.71 (s, 3H), 8.31 (s, 2H), 8.90 (s, 1H). LC-MS: (ES, m/z): [M+1]+ 264.0

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8,Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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 2-iodobenzoic acid (3.0 g, 12.1 mmol) in DMF was added 1,2,3- triazole (1.5 g, 21.7 mmol), Cs2C03(7.1 g, 21.7 mmol), Cul (114 mg, 0.6 mmol), and trans-N,K- dimethylc)rclohexane-l,2-diamine (310 mg, 2.2 mmol). After heating at 120 C for 10 min in a microwave reactor, the mixture was cooled to room temperature, diluted with EtOAc, and filtered through Celite. The filtrate was concentrated in vacuo and the crude residue was purified by silica gel chromatography (MeOH in DCM with 0.1% AcOH) to give Intermediate H as the faster eluting isomer. 1H NMR (DMSO-d6 , 500MHz) delta 13.05 (brs, 1 H), 8.12 (s, 2H), 7.81-7.52 (m, 4H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (0 pag.)WO2016/85784; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 288-36-8 name is 1H-1,2,3-Triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), Cs2CO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-5, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for A-5: 1HNMR (500 MHz, DMSO-d6) d 12.98 (br s , IH), 8.04 (s, 2H), 7.72-7.45 (m, 3H), 2.41 (s, 3H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-1,2,3-Triazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; COLEMAN, Paul, J.; SCHREIER, John, D.; WO2010/48014; (2010); 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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., category: Triazoles

[0260] Bromine (11.59 g, 73.35 mmol) was added dropwise to a 0 C solution of 2H-l,2,3-triazole (5.00 g, 72.46 mmol) in water (50 mL), and the resulting solution was allowed to warm to room temperature and stir overnight. The precipitate was collected by filtration and dried to afford 4,5- dibromo-2H-l ,2,3-triazole (8.00 g, 49%) as a white solid. MS (ESI, pos. ion) m/z 228, 226, 230 [M+H]+.

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

These common heterocyclic compound, 288-36-8, name is 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. Product Details of 288-36-8

Intermediate G To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol), cesium carbonate (89.26 g, 274 mmol), and copper(I) iodide (5.27 g, 27.4 mmol) in DMF (200 mL) were added N,N’-dimethylcyclohexane-l,2-diamine (3.7 mL,23.3 mmol) and lH-l,2,3-triazole (18.92 g, 274 mmol). The resulting mixture was stirred at 110 C overnight, cooled, concentrated in vacuo, and diluted with water (150 mL). The aqueous layer was extracted with EtOAc (300 mL x 3). The aqueous layer was acidified with 2 N HC1 and extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine (150 mL x 3), dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography gel (petroleum ether : EtOAc = 100: 1 – 5 : 1) to provide the title compound as a solid. LRMS m/z (M+H) 208.0 found, 208.0 required.

The synthetic route of 1H-1,2,3-Triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; LUO, Yunfu; (85 pag.)WO2016/100156; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics