Category: 7343-33-1

7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 7343-33-1

Example 6 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100¡ã C. for 36 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered through a plug of Celite? and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as an off white solid (3.78 g, 72.6percent): mp 67-69¡ã C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta -58.02. Example 5 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with potassium phosphate (K3PO4, 7.74 g, 36.5 mmol), CuI (0.165 g, 0.868 mmol), and 3-bromo-1H-1,2,4-triazole (2.83 g, 19.10 mmol). The flask was evacuated/backfilled with N2 (3*). DMF (34.7 mL) was added, followed by trans-(1R,2R)-N,N’-bismethyl-1,2-cyclohexane diamine (0.274 ml, 1.736 mmol) and 1-iodo-4-(trifluoromethoxy)benzene (5.000 g, 17.36 mmol). The solution was heated to 110¡ã C. After 48 h, the reaction mixture was cooled to room temperature, diluted with EtOAc and filtered through Celite?. The filtrate was washed with water (100 mL) containing HCl (1 M, 10 mL. The organics were separated, and the aqueous phase was further extracted with EtOAc (3*). The organics were combined, dried, and concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as a tan solid (1.86 g, 34percent): 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta -58.04; EIMS m/z 307.

Statistics shows that 7343-33-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-1H-1,2,4-triazole.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CREEMER, Lawrence C.; CROUSE, Gary D.; US2014/275502; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 7343-33-1

3-Bromo-1H-1,2,4-triazole (3 g, 20.28 mmol), copper (II) acetate (7.37 g, 40.56 mmol), phenylboronic acid (4.945 g, 40.56 mmol), pyridine (3.208 mL, 40.56 mmol), and crushed and activated 4 A molecular sieves (15 g) were combined in a 1000 mL round bottom flask. The mixture was diluted with dichloromethane (300 mL), and stirred over the weekend with the cap loose at room temperature. The reaction mixture was filtered through Celite and washed with methanol (approximately 100 mL). Celite was added and the mixture was concentrated to dryness under reduced pressure and purified by silica gel chromatography (80 gram Gold column (ISCO); 0-100percent ethyl acetate/hexane). Possible regioisomer observed in 1H NMR and in LC/MS (impurity runs faster). No separation on normal phase. Combined the desired fractions and concentrated to dryness under reduced pressure. The enriched material was diluted with dimethylsulfoxide and purified by reverse phase chromatography (275 gram Gold C-18 column (ISCO); 10-100percent acetonitrile/water with trifluoroacetic acid modifier). The pure fractions were concentrated to dryness under reduced pressure to give 3-bromo-1-phenyl-1,2,4- triazole (1.72 g, 38percent). 1H NMR (400 MHz, OMSO-de) delta 9.31 (s, 1H), 7.88 – 7.76 (m, 2H), 7.65 – 7.52 (m, 2H), 7.46 (t, J = 7.4 Hz, 1H) ppm. ESI-MS m/z calc. 222.9745, found 223.97 (M+l)+; Retention time: 2.66 minutes.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 7343-33-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BETHIEL, Randy Scott; CAO, Jingrong; COLLIER, Philip, N.; DAVIES, Robert J.; DOYLE, Elisabeth; FRANTZ, James Daniel; GOLDMAN, Brian Anthony; GREY, Ronald Lee; GRILLOT, Anne-laure; GU, Wenxin; KOLPAK, Adrianne Lynne; KRAUSS, Paul Eduardo; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MESSERSMITH, David; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; WANG, Jian; (491 pag.)WO2018/106646; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-33-1, The chemical industry reduces the impact on the environment during synthesis 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

To a 250 mL reaction flask was added 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100¡ã C. for 20 hours (h). The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite?. The Celite? was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography using EtOAc/hexanes as eluent to yield the title compound (3.78 g, 73percent): mp 69-70¡ã C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta ?58.04; EIMS m/z 307 ([M]+).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; WHITEKER, Gregory T.; US2014/275560; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7343-33-1 name is 5-Bromo-1H-1,2,4-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. 7343-33-1

A dry round bottom flask was charged with 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100¡ã C. for 36 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered through a plug of Celite? and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash chromatography (silica/EtOAc/Hexanes) yielded 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole as an off white solid (3.78 g, 73percent yield): mp 67-69¡ã C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta -58.02.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1H-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; Dow AgroSciences LLC; DENT, III, William Hunter; GIAMPIETRO, Natalie C.; US2014/275564; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-33-1, Adding a certain compound to certain chemical reactions, such as: 7343-33-1, name is 5-Bromo-1H-1,2,4-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 7343-33-1.

EXAMPLE 6 fPROCEDURES)(1 S,4a/?,6aS,7/?,8/?, 1 Oa/?, 10b/?, 12a/?, 1 AR, 15R)- 15-[[(2/?)-2-amino-2,3- dimethylbutyl]oxy]-14-(3-bromo-4H-l,2,4-triazol-4-yl)-8-[(l/?)-l,2-dimethylpropyl]-1 ,6,6a,7,8,9, 10, 10a, 10b, 11 , 12, 12a-dodecahydro- 1 ,6a,8, 10a-tetramethyl-4//- 1 ,4a-propano-2H- phenanthro[l,2-c]pyran-7-carboxylic acid (EXAMPLE 6A) and(1 S,4a/?,6aS,7/?,8/?, 1 Oa/?, 10b/?, 12a/?, 14/?, 15R)- 15-[[(2/?)-2-amino-2,3- dimethylbutyl]oxy]-14-(5-bromo-/H-l,2,4-triazol-l-yl)-8-[(l/?)-l,2-dimethylpropyl]-1 ,6,6a,7,8,9, 10, 10a, 10b, 11 , 12, 12a-dodecahydro- 1 ,6a,8, 1 Oa-tetramethyl-4//- 1 ,4a-propano-2H- phenanthro[l,2-c]pyran-7-carboxylic acid (EXAMPLE 6B) and( 1 S,4aR,6aS,7R,8R, 1 Oa/?, 1 Obi?, 12aK, 1 AR, 15R)- 15-[[(2i?)-2-amino-2,3- dimethylbutyl]oxy]-14-(3-bromo-7H-l,2,4-triazol-l-yl)-8-[(li?)-l,2-dimethylpropyl]- 1 ,6,6a,7,8,9, 10, 1 Oa, 1 Ob, 11 , 12, 12a-dodecahydro- 1 ,6a,8, 1 Oa-tetramethyl-^H- 1 ,4a-propano-2H- phenanthro[l,2-c]pyran-7-carboxylic acid (EXAMPLE 6C)3-bromo-lH-l,2,4-triazole (32.1 mg, 0.217 mmol) and BF3OEt2 (54 mul, 0.426 mmol) were added to a stirred solution of Intermediate 6 (26.0 mg, 0.043 mmol) in 1,2- dichloroethane (0.43 ml). The reaction mixture was a light yellow solution that was heated to 5O0C. After 1.75 hr, LCMS and 1H NMR showed complete consumption of Intermediate 6. The reaction mixture was cooled to room temperature, the solvent was evaporated, and the resulting residue was placed under high vacuum. The residue was dissolved in methanol and separated using a single HPLC run on a 19 x 150 mm Sunfire Prep Cl 8 OBD 10 mum column by eluting with acetonitrile/water + 0.1percent TFA. The HPLC fractions containing the fastest eluting regioisomer were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give EXAMPLE 6A (3.6 mg) as a white solid. The HPLC fractions containing the second eluting regioisomer were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give EXAMPLE 6B (13.1 mg) as a white solid. The HPLC fractions containing the slowest eluting regioisomer were combined, the solvent was evaporated under reduced pressure, and the residue was lyophilized from ethanol and benzene to give EXAMPLE 6C (5.8 mg) as a white solid.EXAMPLE 6A: 1H NMR (CD3OD, 600 MHz, ppm) delta 0.76 (s, 3H, Me), 0.76 (d, 3H, Me), 0.81 (d,3H, Me), 0.84 (d, 3H, Me), 0.85 (d, 3H, Me), 0.88 (s, 3H, Me), 0.89 (d, 3H, Me), 0.94 (s, 3H, Me), 1.16 (s, 3H, Me), 1.20 (s, 3H, Me), 1.22-1.35 (m), 1.40-1.44 (m), 1.46-1.65 (m), 1.73-1.96 (m), 2.11-2.22 (m), 2.43 (broad dd, IH, H13), 2.79 (broad d, IH), 2.84 (s, IH, H7), 3.49 (d, IH), 3.53 (d, 2H), 3.60 (d, IH), 3.73 (broad d, IH), 3.94 (d, IH), 5.50 (dd, IH, H5), 5.72-5.80 (broad m, IH, H 14), 9.29 (broad s, IH, triazole).Mass Spectrum: (ESI) m/z = 717.32 (719.32) (M+H).EXAMPLE 6B:1H NMR (CD3OD, 600 MHz, ppm) delta 0.75 (s, 3H, Me), 0.76 (d, 3H, Me), 0.79 (d, 3H, Me), 0.83 (d, 3H, Me), 0.84 (d, 3H, Me), 0.88 (s, 3H, Me), 0.89 (d, 3H, Me), 0.91 (s, 3H, Me), 1.13 (s, 3H, Me), 1.19 (s, 3H, Me), 1.22-1.34 (m), 1.39-1.43 (m), 1.46-1.56 (m), 1.58-1.64 (m), 1.72-1.95 (m), 2.09-2.21 (m), 2.30 (dd, IH, H13), 2.83 (s, IH, H7), 2.85 (d, IH), 3.48 (d, IH), 3.48 (d, IH), 3.54 (dd, IH), 3.60 (d, IH), 3.88 (d, IH), 3.95 (d, IH), 5.47 (dd, IH, H5), 5.71-5.77 (m, IH, H14), 8.10 (s, IH, triazole). Mass Spectrum: (ESI) m/z = 717.32 (719.32) (M+H).EXAMPLE 6C:1H NMR (CD3OD, 600 MHz, ppm) delta 0.76 (s, 3H, Me), 0.77 (d, 3H, Me), 0.82 (d, 3H, Me), 0.85 (d, 3H, Me), 0.86 (s, 3H, Me), 0.86 (d, 3H, Me), 0.89 (d, 3H, Me), 0.92 (s, 3H, Me), 1.16 (s, 3H, Me), 1.20 (s, 3H, Me), 1.22-1.34 (m), 1.39-1.44 (m), 1.48-1.65 (m), 1.76-1.96 (m), 2.11-2.22 (m), 2.41 (dd, IH, H13), 2.72 (d, IH), 2.84 (s, IH, H7), 3.47 (d, IH), 3.50 (d, IH), 3.52 (dd, IH), 3.58 (d, IH), 3.72 (d, IH), 3.91 (d, IH), 5.48 (dd, IH, H5), 5.51-5.57 (m, IH, H 14), 8.52 (s, IH, triazole).Mass Spectrum: (ESI) m/z = 717.32 (719.32) (M+H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromo-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GREENLEE, Mark, L.; WILKENING, Robert; APGAR, James; WILDONGER, Kenneth, James; MENG, Dongfang; PARKER, Dann, L.; WO2010/19203; (2010); 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. 7343-33-1, name is 5-Bromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., 7343-33-1

2- [6-Chloro-3- (ethanesulfonyl) pyridin-2-yl] -3-methyl-6- (trifluoromethyl)-3H-imidazo [4,5-b] 300mg, potassium carbonate 133 mg, and to a mixture of 3 mL of DMF, was added 3-bromo-1H-1,2,4-triazole 132mg under ice-cooling. After the mixture was stirred under ice-cooling for 2.5 hours, a saturated aqueous solution layer was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and saturated brine, and dried with anhydrous sodium sulfate. The resulting organic layer was dried under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 370mg of the compound of the present invention beta3 referred to below.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; NAKAJIMA, YUJI; OKAWARA, YUICHI; (263 pag.)JP2016/102104; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics