Tag: M.W:200-300

Related Products of 342617-08-7, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 342617-08-7, name is 3-(3-Bromophenyl)-4H-1,2,4-triazole, molecular formula is C8H6BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

B. 3-(3-(TrimethylstannyI)phenyl)-lH-l,2,4-triazole. A solution of 3-(3- bromophenyl)-lH-l,2,4-triazole (0.5 g, 2.25 mmol) in dry toluene (20 mL) was treated with hexamethylditin (0.88 g, 2.70 mmol) and tetrakis(triphenylphosphine)palladium(0) (255 mg, 0.22 mmol) in a sealed tube at 110 C for 2.5 h. The volatiles were removed under reduced pressure and the crude product was purified by biotage (0-50% ethyl acetate in hexanes) to afford the desired stannane (200 mg, 29%). MS (ESI) m/z 310.3[M+l]+.

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Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 20725-34-2, name is 1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H8BrN3O2

In a 20 mL reaction vial, l-(4-bromo-phenyl)-5-methyl-lH-[l ,2,3]triazole-4-carboxylic acid (0.67 g, 2.38 mmol), (R)-l-phenylethanol (0.29 g, 0.29 mL, 2.4 mmol) and triethylamine (0.24 g, 0.33 mL, 2.4 mmol) were combined with toluene (100 mL) to give a yellow solution and to this was added diphenylphosphorylazide (0.65 g, 0.5 mL, 2.4 mmol). The vial’s atmosphere was purged with nitrogren, sealed, heated in a dry block at 80 C for 4 h, and cooled to room temperature overnight. The reaction was diluted with EtOAc (100 mL) and washed with water (100 mL) and brine (50 mL). The aqueous layers were extracted with EtOAc (100 mL). The organic layers were combined, dried over MgS04, filtered, concentrated, dissolved in minimal DCM, and purified by flash chromatography (silica gel, 0% to 25% EtOAc in hexanes). Appropriate fractions combined, concentrated, dried from DCM / hexanes, to give [l-(4-bromo-phenyl)-5-methyl-lH-[l ,2,3]triazol-4-yl]-carbamic acid (R)-l-phenyl-ethyl ester (0.507 g, 53.2% yield) as an off-white solid. LC/MS calcd. for Ci8Hi7BrN402 (m/e) 400/402, obsd. 401/403 (M+H, ES+).

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law. In my other articles, you can also check out more blogs about 20725-34-2, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GABRIEL, Stephen Deems; HAMILTON, Matthew Michael; QIAN, Yimin; SIDDURI, Achyutharao; WO2013/189865; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 1186050-58-7, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid, molecular formula is C9H6FN3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a solution of (S)-2,7-dimethyl-3-(3,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridine (15 mg, 53.3 mumol) (Intermediate 40) in CH2Cl2 (0.48 mL) was added 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (prepared according to methods described in Pat. Pub. No. WO2012145581, Oct. 26, 2012) (12.2 mg, 58.7 mumol), HATU (26.4 mg, 69.3 mumol), and N,N-diisopropylethylamine (27.6 muL, 0.16 mmol). After stirring at room temperature for 30 min, the mixture was concentrated in vacuo and purified by preparative HPLC (XBridge C18 column (5 mum, 100*4.6 mm), mobile phase of 5-95% ACN in 20 mM aqueous NH4OH) to afford the title compound as a white powder (21 mg, 84% yield). MS (ESI): mass calcd. for C23H18F4N6O, 470.1; m/z found, 471.2 [M+H]+. 1H NMR (600 MHz, DMSO-d6) delta 8.19-8.05 (m, 1.62H), 7.93-7.90 (m, 0.40H), 7.87-7.83 (m, 0.91H), 7.74-7.66 (m, 1H), 7.59-7.38 (m, 3H), 5.59-5.49 (m, 0.74H), 4.73-4.62 (m, 0.28H), 4.57-4.51 (m, 0.17H), 3.81 (s, 2.26H), 3.76 (s, 0.22H), 3.70 (s, 0.52H), 3.64-3.52 (m, 0.72H), 3.38-3.17 (m, 0.73H), 3.07-3.00 (m, 0.22H), 2.84-2.76 (m, 0.15H), 2.71-2.60 (m, 0.63H), 2.45-2.22 (m, 1.47H), 1.47 (d, J=6.7 Hz, 2.28H), 1.35 (d, J=6.8 Hz, 0.6H).

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Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Chen, Gang; Huang, Chaofeng; Laforteza, Brian Ngo; Ravula, Suchitra; Southgate, Emma Helen; Zhang, Wei; US2020/102303; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1257633-67-2, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 1257633-67-2, name is 1-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole, molecular formula is C11H21N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a 50-mL round bottom flask was added a solution of 1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole (1.28 g, 5.63 mmol) in dichloromethane (6.0 mL), followed by addition of water (3.0 mL) and trifluoroacetic acid (1.0 mL) The reaction mixture was stirred vigorously under nitrogen for 3 h and then was diluted with EtOAc (100 mL), washed with sat aq NaHCO3 (3×40 mL) and brine (40 mL). The combined organic phases were dried over anhydrous MgSO4, filtered. Solvent was removed and the residue was used in the next step without purification. 1H NMR complies with the reported value.

Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 1-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCACATION; Zeng, Dexing; (26 pag.)US2017/297008; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 7411-23-6

a 3,5-Dibromo-1-(4-methoxyphenylmethyl)-1H-1,2,4-triazole 4-Methoxyphenylmethyl chloride (4.47 ml) was added to a stirred solution of 3,5-dibromo-1,2,4-triazole (7.125 g) and triethylamine (4.81 ml) in anhydrous dichloromethane (70 ml) at room temperature. After 4 days, the mixture was evaporated under reduced pressure and the residue purified by column chromatography over silica, eluding with ethyl acetate/isohexane (1:4) to give the sub-title compound (7.34 g) as a solid. MS (+ve APCI) 346/348/350 ((M+H)+).

I hope this article can help some friends in scientific research. I am very proud of our efforts over the past few months and hope to 3,5-Dibromo-1H-1,2,4-triazole help many people in the next few years.

Reference:
Patent; Bantick, John; Ingall, Anthony; Perry, Matthew; Reynolds, Rachel; US2004/14634; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 118863-62-0, New Advances in Chemical Research in 2021. The appropriate choice of redox mediator can avoid electrode passivation and overpotential, which strongly inhibit the efficient activation of substrates in electrolysis. 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, molecular formula is C8H6BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Into a 1000 mL 3-necked flask, was placed a solution of ethyl 4- bromobenzenecarboximidoate (54.0 g, 237 mmol) in xylene (500 mL). To the mixture was added NH2NHCHO (14.22 g, 237 mmol). The resulting solution was heated to reflux overnight. The reaction mixture was cooled in an ice bath and filtered. The solid was washed with 700 mL of petroleum ether and dried in an oven under reduced pressure to afford 3-(4-bromophenyl)-lH- 1,2,4-triazole (crude) as a white solid.Into a 500 mL 3-necked flask was placed a solution of 3-(4-bromophenyl)-lH- 1,2,4-triazole (2.24 g, 10.0 mmol) in TetaF (200 mL). To this was added TEA (1.10 g, 10.9 mmol). To the mixture was added BoC2O (2.39 g, 11.0 mmol). The resulting solution was stirred overnight at room temperature. The mixture was evaporated, and the residue was purified by chromatography (1 :20 EtOAc/PE) to provide tert-butyl 3-(4-bromophenyl)-4H-l,2,4-triazole- 4-carboxylate as a white solid.Into a 2000 mL 3-necked flask was placed a solution of tert-butyl 3-(4- bromophenyl)-4H-l ,2,4-triazole-4-carboxylate (80.0 g, 247 mmol) in CH2Cl2 (800 mL). To the mixture was added TFA (400 mL). The resulting solution was stirred at room temperature for 1 h. The reaction was evaporated to provide 3-(4-bromophenyl)-l//-l,2,4-triazole as a white solid. 1H NMR (300 MHz, DMSOd6) 8.52 (s, IH), 7.97 (d, 2H), 7.69 (d, 2H). Calc’d for C8H7BrN3 [M+H]+ 224, found 224.

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Reference:
Patent; MERCK & CO., INC.; WO2008/156726; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1257633-67-2, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 1257633-67-2, name is 1-(tert-Butyl)-4-(diethoxymethyl)-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 50-mL round bottom flask was added a solution of 1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole (1.28 g, 5.63 mmol) in dichloromethane (6.0 mL), followed by addition of water (3.0 mL) and trifluoroacetic acid (1.0 mL) The reaction mixture was stirred vigorously under nitrogen for 3 h and then was diluted with EtOAc (100 mL), washed with sat aq NaHCO3 (3×40 mL) and brine (40 mL). The combined organic phases were dried over anhydrous MgSO4, filtered. Solvent was removed and the residue was used in the next step without purification. 1H NMR complies with the reported value.

The potential utility of systematic synthetic strategy will be applicable to efficient generations of chemical libraries of compounds to find ‘hit’ molecules.Read on for other articles about 1-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole, hurry up and to see.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCACATION; Zeng, Dexing; (26 pag.)US2017/297008; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 22300-52-3, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-triazole, molecular formula is C2HBr2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1?3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5?10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C?N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

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Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7411-23-6, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-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.

Two hatches of phenylboronic acid (13 5 g, 111 mmol, 1.0 eq), 3,5-dibromo~lH-i,2,4~ triazoe (25 g, 110 mmol, 1.0 eq), Cu(QAc)2 (30 g, 165 mmol, 1.5 eq), pyridine (26.5 g, 335 mmol, 27 mL, 3.0 eq) and 4A MS (5 g, 22.0 mmol) in toluene (250 mJL) was degassed and purged with O2 for three times, and then the mixture was stirred at 80 C for 16 h under O? atmosphere (15 psi). After completion of the reaction, the two batches of reaction mixture were mixed and filtered, then concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (ISCO; 200 g SepaFlash1 Silica Flash Column, eluent of 0-10% ethyl acetate/petroleum ether gradient 80 mL/min) to give 36 g crude product with 67% purity. 2 g was used for next step directly. The remaining 34 g was diluted with DCM (200 mL) and washed with saturated aqueous NaHC03 (100 mL c 1), brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give 3, 5-dibromo-l -phenyl-1 ,2,4-triazole (29.2 g, 37% yield, 85% purity) as a light yellow solid. i.C-YlS (ESI): m/z (M+H) 303.9.

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Reference:
Patent; AN2H DISCOVERY LIMITED; JOHNSTON, Jennifer; FATHEREE, Paul Ross; (225 pag.)WO2019/109099; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

Bis(triphenylphosphine)palladium(II) chloride (0.087 g, 0.12 mmol) was added to a stirred mixture of tert-butyl N-tert-butoxycarbonyl-N-[3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-trimethylstannyl-2-pyridyl]carbamate 5a (3 g, 4.13 mmol), 3,5-dibromo-1-methyl-1,2,4-triazole 27 (1 g, 4.15 mmol) and lithium chloride (0.528 g, 12.4 mmol) dissolved in DME (8 mL) under argon. The resulting mixture was heated at 140 C for 30 min in a microwave apparatus. More bis(triphenylphosphine)palladium(II) chloride (0.087 g, 0.12 mmol) was added and the mixture was heated at 130 C for 30 min in the microwave. The mixture was evaporated under reduced pressure, adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 5 to 50% ethyl acetate in dichloromethane to afford tert-butyl N-[5-(5-bromo-2-methyl-1,2,4-triazol-3-yl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (1.4 g, 58%) as a solid. Bis(triphenylphosphine)palladium(II) chloride (170 mg, 0.24 mmol) was added to a stirred mixture of tert-butyl N-[5-(5-bromo-2-methyl-1,2,4-triazol-3-yl)-3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (1.40 g, 2.42 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate 28 (748 mg, 2.42 mmol) and cesium fluoride (1.10 g, 7.26 mmol) in methanol (4 mL) under argon atmosphere. The resulting mixture was heated at 140 C for 40 min in a microwave apparatus. More bis(triphenylphosphine)palladium(II) chloride (1.02 g, 1.45 mmol) was added and the mixture was degassed and heated at 140 C for 30 min in the microwave. After cooling, the mixture was adsorbed on silica gel with methanol / ammonia and was purified by flash chromatography on silica gel eluting with 1 to 4% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford tert-butyl 4-(5-(6-(tert-butoxycarbonylamino)-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-1-methyl-1,2,4-triazol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (956 mg, 68%) as a yellow solid. A slurry of palladium (175 mg, 1.65 mmol) and tert-butyl 4-(5-(6-(tert-butoxycarbonylamino)-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-1-methyl-1,2,4-triazol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (956 mg, 1.65 mmol) and ammonium formate (1.04 g, 16.5 mmol) dissolved in DMF (30 mL) was heated at 70 C for 2 h. More palladium (175 mg, 1.65 mmol) was added. The mixture was heated one more hour. The resulting slurry was filtered and the filtrate was concentrated to dryness. Water (50 mL) was added. The mixture was stirred for 1 h, filtered and dried under reduced pressure to afford crude tert-butyl 4-(5-(6-(tert-butoxycarbonylamino)-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-1-methyl-1,2,4-triazol-3-yl)piperidine-1-carboxylate (562 mg, 59%) as a yellow solid. Trifluoroacetic acid (1.5 mL) was added to a stirred suspension of tert-butyl 4-(5-(6-(tert-butoxycarbonylamino)-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)-1-methyl-1,2,4-triazol-3-yl)piperidine-1-carboxylate (562 mg, 0.96 mmol) in dichloromethane (2 mL). The resulting solution was stirred at 25 C for 1 h. The solvents were evaporated. Traces of TFA were removed by azeotroping with toluene. The crude product was dissolved in methanolic solution of ammonia, adsorbed on silica gel, and purified by flash chromatography on silica gel eluting with 2 to 8% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1,2,4-triazol-5-yl)pyridin-2-amine (332 mg, 90%) as a beige solid. Acetyl chloride (0.022 mL, 0.31 mmol) was added over a period of 15 min to a stirred solution of 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1,2,4-triazol-5-yl)pyridin-2-amine (100 mg, 0.26 mmol) and triethylamine (0.073 mL, 0.52 mmol) dissolved in dichloromethane (3 mL) at 0 C. The resulting solution was stirred at 0C for 1 hour. The mixture was adsorbed on silica gel with a 7 N methanolic solution of ammonia. The crude product was purified by flash chromatography on silica gel eluting with 2 to 4% methanolic ammonia (7 N) in dichloromethane. The solvent was evaporated to dryness to afford 1-[4-[5-[6-amino-5-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]-1-methyl-1,2,4-triazol-3-yl]-1-piperidyl]ethanone 5 (80 mg, 72%) as a yellow foam.

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Reference:
Article; Barlaam, Bernard; Cosulich, Sabina; Delouvrie, Benedicte; Ellston, Rebecca; Fitzek, Martina; Germain, Herve; Green, Stephen; Hancox, Urs; Harris, Craig S.; Hudson, Kevin; Lambert-Van Der Brempt, Christine; Lebraud, Honorine; Magnien, Francoise; Lamorlette, Maryannick; Le Griffon, Antoine; Morgentin, Remy; Ouvry, Gilles; Page, Ken; Pasquet, Georges; Polanska, Urszula; Ruston, Linette; Saleh, Twana; Vautier, Michel; Ward, Lara; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5155 – 5162;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics