23579-79-5 - | Triazoles

September 27, 2021 News Continuously updated synthesis method about 23579-79-5

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Application of 23579-79-5, New Advances in Chemical Research 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, molecular formula is C3H3Br2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

In a 50 mL pressure vial, 3,5-dibromo-1-methyl-1H-1,2,4-triazole (Int-41, 1.42 g, 5.89 mmol) was dissolved in DMF (12 mL) and potassium carbonate (1.36 mg, 9.82 mmol), followed by 3- chloro-5-methylphenol (700 mg, 4.91 mmol) were added. The vial was sealed, the reaction mixture was stirred for 15 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 25:75 v/v) to yield the title compound as white solid (1.37 g, 92%). 1H NMR (CDC13, 300 MHz): delta 2.37 (s, 3 H), 3.77 (s, 3 H), 6.99-7.02 (m, 1 H), 7.06-7.08 (m, 1 H), 7.11- 7.14 (m, 1 H). MS (ES+) m/z 302.0, 304.0, 306.0 [M+H, Br & CI isotopes] .

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

13-Sep-2021 News The Best Chemistry compound: 23579-79-5

The catalyzed pathway has a lower Ea, but the net change in energy that results from the reaction is not affected by the presence of a catalyst. In my other articles, you can also check out more blogs about 23579-79-5

Research speed reading 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. SDS of cas: 23579-79-5

Intermediate 8 3-Bromo-l-methyl-5-(2-phenylazetidin iazole 3,5-Dibromo-l-methyl-lH-l,2,4-triazole (200 mg, 0.83 mmol) and 2-phenylazetidine (177 mg, 1.33 mmol) were dissolved in DMF (5 mL). Potassium carbonate (344 mg, 2.49 mmol) was added. The mixture was heated at 170C for 2 hour in a microwave reactor. The mixture was cooled to rt, diluted with water and extracted with diisopropyl ether. The organic layer was washed with brine and dried over sodium sulfate. The solvents were removed to give the title compound as a liquid (225 mg, 92%). MS (ESI+) m/z 294 [M+H]+. XH NMR (400 MHz, CDCI3) delta ppm 2.37 – 2.49 (m, 1 H) 2.71 – 2.82 (m, H) 3.39 (s, 3 H) 4.11 – 4.19 (m, 2 H) 5.38 (t, 1 H) 7.28 – 7.48 (m, 6 H).

Reference:
Patent; ACTURUM LIFE SCIENCE AB; BESIDSKI, Yevgeni; YNGVE, Ulrika; PAULSEN, Kim; LINDE, Christian; NORDVALL, Gunnar; MACSARI, Istvan; MALMBORG, Jonas; WO2014/195321; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Reference of 23579-79-5, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 23579-79-5, name is 3,5-Dibromo-1-methyl-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.

a) 5-Bromo-2-methyl-2H-[ 1 ,2,4]triazole-3-carbaldehyde To a solution of 3,5-dibromo-l-methyl-lH-l,2,4-triazole (500 mg, 2.08 mmol, Eq: 1.00) in tetrahydrofuran (5 ml) was added dropwise at -45 C under argon atmosphere n-butyllithium 1.6 M in hexane (1.56 ml, 2.49 mmol, Eq: 1.2). The resulting mixture was stirred for 30 minutes at -45C and was then cooled to -70C. Then dimethyl formamide (197 mg, 209 mu, 2.7 mmol, Eq: 1.3) wass added dropwise. After 15 minutes the cooling bath was removed and the mixture was allowed to reach 25 C. The mixture was stirred for additional 2 hours at 25 C. The mixture was poured on water and extracted twice with ethyl acetate, the organic layers were combined, washed with water and brine, dried over magnesium sulfate, filtrated and evaporated, affording 5-bromo-2-methyl-2H-[l,2,4]triazole-3-carbaldehyde (218 mg / 55.3 %) as an orange semi solid. MS: m/e= 189 (M+H+)

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Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KUHN, Bernd; LERNER, Christian; RUDOLPH, Markus; SCHAFFHAUSER, Herve; WO2013/178572; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Application of 23579-79-5, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 23579-79-5, name is 3,5-Dibromo-1-methyl-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.

In a 10 mL pressure vial, 3,5-dibromo-1-methyl-1H-1,2,4-triazole (lnt-41, 181 mg, 752 muiotaetaomicron) was dissolved in DMF (2 mL) and potassium carbonate (160 mg, 1.16 mmol), followed by 3- (trifluoromethoxy)phenol (103 mg, 74.7 mu, 578 muiotaetaomicron) were added. The vial was sealed, the reaction mixture was stirred for 18 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n- heptane, gradient 0: 100 to 20:80 v/v) to yield the title compound as colorless liquid (187 mg, 95%). HPLC (method LCMS_fastgradient) tR= 1.28 min. 1H NMR (CDCl3, 300 MHz): delta 3.79 (s, 3 H), 7.11-7.16 (m, 1 H), 7.20-7.24 (m, 1 H), 7.29-7.33 (m, 1 H), 7.45 (t, J = 8.3 Hz, 1 H). MS (ES+) m/z 338.1, 340.1 [M+H, Br isotopes] .

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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 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, hurry up and to see.

Synthetic Route of 23579-79-5, 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. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

In a 25 mL pressure vial, 3,5-dibromo-1-methyl- 1H-1,2,4-triazole (lnt-41, 424 mg, 1.76 mmol) was dissolved in DMF (5 mL) and potassium carbonate (375 mg, 2.71 mmol), followed by 3- chlorophenol (176 mg, 141 L, 1.36 mmol) were added. The vial was sealed, the reaction mixture was stirred for 15 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 30:70 v/v) to yield the title compound as white solid (388 mg, 99%). 1H NMR (CDCl3, 300 MHz): delta 3.78 (s, 3 H), 7.21-7.28 (m, 2 H), 7.32-7.39 (m, 2 H). MS (ES+) m/z 288.0, 290.0, 292.0 [M+H, Br & CI isotopes] .

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New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 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. Safety of 3,5-Dibromo-1-methyl-1H-1,2,4-triazole

In a 50 mL pressure vial, 3,5-dibromo-1-methyl-1H-1,2,4-triazole (Int-41, 1.47 g, 6.1 mmol) was dissolved in DMF (13 mL) and potassium carbonate (1.53 mg, 11.1 mmol), followed by 3-fluoro-5-methylphenol (700 mg, 5.55 mmol) were added. The vial was sealed, the reaction mixture was stirred for 15 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 25:75 v/v) to yield the title compound as light yellow solid (1.23 g, 75%). 1H NMR (CDCl3, 300 MHz): delta 2.38 (s, 3 H), 3.77 (s, 3 H), 6.76-6.82 (m, 1 H), 6.84-6.91 (m, 2 H). MS (ES+) m/z 286.0, 288.0 [M+H, Br isotopes] .

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a) 1 -(5-Bromo-2-methyl-2H-[ 1 ,2,4]triazol-3-yl)-ethanol To a solution of 3,5-dibromo-l-methyl-lH-l,2,4-triazole (2.634 g, 10.9 mmol, Eq: 1.00) in tetrahydrofuran (184 ml) was added dropwise at -78 C under argon atmosphere n- butyllithium 1.6 M in hexanes (6.83 ml, 10.9 mmol, Eq: 1.00). The resulting mixture was stirred for 20 minutes at -75 C then a solution of acetaldehyde (1.2 g, 1.54 ml, 27.3 mmol, Eq: 2.5) in tetrahydrofuran (36.9 ml) was added slowly and stirring at -75 C was continued for further 1.5 hours. The mixture was quenched with sat. aq. NH4C1 solution and was warmed to 25 C. The mixture was diluted with ethyl acetate and washed 2 times with water. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording l-(5-bromo-2- methyl-2H-[l,2,4]triazol-3-yl)-ethanol (1.639 g, 72.7%) as a light yellow oil. MS: m/z= 206/209 (M+H+)

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The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about 3,5-Dibromo-1-methyl-1H-1,2,4-triazole is helpful to your research.

Related Products of 23579-79-5, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Intermediate 3 3-Bromo-/V-(cyclopropylmethyl)-l-methyl-lH-l,2,4-triazol-5-amine To a solution of 3,5-dibromo-l-methyl-l/-/-l,2,4-triazole (0.700 g, 2.90 mmol) and cyclopropanemethylamine (0.50 mL, 5.8 mmol) in 1,4-dioxane (2.5 mL) and DMA (1 mL) was added Lambda/,/V-diisopropylethylamine (0.47 mL, 5.8 mmol). The mixture was heated at 130C in a sealed tube for 16 h and then cooled down to rt. Water (5 mL) was added and the resulting solution was extracted with EtOAc (3 x 15 mL). The combined organic layers were washed with water (10 mL) and brine (10 mL), dried over sodium sulfate and concentrated. The residue was triturated with MTBE to give the title compound as a solid (0.330 g, 49%). XH NMR (400 MHz, CDCI3): delta ppm 0.23 – 0.27 (m, 2 H), 0.53 – 0.58 (m, 2 H), 1.05 – 1.16 (m, 1 H), 3.23 (dd, 2 H), 3.56 (s, 3 H), 3.97 (br s, 1 H).

Reference:
Patent; ACTURUM LIFE SCIENCE AB; BESIDSKI, Yevgeni; YNGVE, Ulrika; PAULSEN, Kim; LINDE, Christian; MALMBORG, Jonas; WO2014/195322; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Related Products of 23579-79-5, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 23579-79-5, name is 3,5-Dibromo-1-methyl-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.

A mixture of 17.5 g (0.073 mol) of triazole 2a and 36.5 mL (0.73 mol) of 98 % hydrazine hydrate in 150 mL of propan-2-ol was refluxed for 5.5 h with stirring. The mixture was cooled, the precipitate was filtered off, and the filtrate was evaporated to a volume of 15 mL to isolate an additional amount of the product which was combined with the main portion and recrystallized from toluene. Yield 11.6 g (83 %), mp 196-197 C. IR spectrum, nu, cm-1: 3325 (NH), 3256, 2924,1634 (NH), 1582, 1521, 1456, 1437, 1429, 1331, 1294, 1246, 1227, 1132, 1024, 999, 947, 866, 731, 681, 608, 567, 557. 1H NMR spectrum, delta, ppm: 3.51 s (3H,CH3), 4.52 br.s (2H, NH2, overlapped by the signal of water present in the solvent), 7.84 s (1H, NH). 13C NMR spectrum, deltaC, ppm: 34.3 (CH3), 135.5 (C3),159.5 (C5). Mass spectrum, m/z (Irel, %): 193 (61.3) [M]+, 191 (64.2) [M]+, 178 (4.8), 177 (8.2), 176 (8.2), 175 (10.0), 174 (2.9), 164 (3.1), 163 (4.1), 161 (9.1), 159 (8.2), 136 (5.3), 135 (9.4), 134 (6.3), 133 (11.4), 112 (70.4), 108 (16.0), 106 (16.1), 95 (13.0), 83 (43.0), 82 (47.8), 81 (8.6), 80 (5.7), 78 (6.9), 68 (5.9), 56 (7.6), 55 (18.1), 53 (30.6), 43 (100), 42 (32.7), 41 (7.9), 40 (7.3), 31 (18.6), 30 (37.6), 29 (18.8), 28 (11.8), 27 (7.5), 17 (5.7), 16 (8.9), 15 (39.4). Found,%: C 19.07; H 3.11; N 36.87. C3H6BrN5. Calculated, %: C 18.77; H 3.15; N 36.47. M 192.02.

Reference:
Article; Tolstyakov; Russian Journal of Organic Chemistry; vol. 54; 10; (2018); p. 1537 – 1547; Zh. Org. Khim.; vol. 54; 10; (2018); p. 1525 – 1534,10;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Application of 23579-79-5, New Advances in Chemical Research in 2021.In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

In a 25 mL round bottomed flask, 3,5-dibromo-1-methyl-1H-1,2,4-triazole (Int-41, 442 mg, 1.84 mmol) was dissolved in DMF (4 mL) and potassium carbonate (483 mg, 3.5 mmol), followed by 3-fluorophenol (200 mg, 1.75 mmol) were added. The reaction mixture was stirred for 18 h at 100 C. After cooling, it was concentrated in vacuo, the residue was purified directly by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 20:80 v/v) to afford the title compound as white solid (397 mg, 83%). HPLC (method LCMS_fastgradient) tR= 1.05 min. 1H NMR (CDCl3, 300 MHz): delta 3.78 (s, 3 H), 6.94-7.02 (m, 1 H), 7.06-7.14 (2 H), 7.34-7.43 (m, 1 H). MS (ES+) m/z 272.1, 274.1 [M+H, Br isotopes].

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