Month: February 2021

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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 171290-52-1

1-(Benzenesulfonyl)-5-[2-(3,5-dimethoxyphenyl)ethynyl]-1H-pyrrolo[2,3-b]pyridine 1-(Benzenesulfonyl)-5-bromo-1H-pyrrolo[2,3-b]pyridine (639.0 mg, 1.90 mmol), 1-ethynyl-3,5-dimethoxybenzene (461.0 mg, 2.84 mmol), copper(1+) iodide (36.1 mg, 0.19 mmol) and DIPEA (1.62 ml, 9.48 mmol) were dissolved in MeCN (10 ml). Reaction mixture was degassed with nitrogen for 5 mins. Palladium tetrakis triphenylphospine (109.5 mg, 0.09 mmol) was added and reaction heated to 80C in a sealed tube for 90 mins. Reaction mixture was cooled to RT, partitioned between saturated aq. NaHCO3 solution and EtOAc and organics separated. Organics were washed with brine, dried, filtered and concentrated. Crude material was purified by FCC on Biotage (0 – 50% EtOAc / Heptane) to give the title compound as a yellow solid (867.0 mg, 100%). 1H NMR (500 MHz, Chloroform-d) delta 8.59 (d, J = 1.9 Hz, 1H), 8.27 – 8.12 (m, 2H), 8.00 (d, J = 1.9 Hz, 1H), 7.78 (d, J = 4.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 7.52 (t, J = 7.8 Hz, 2H), 6.71 (d, J = 2.3 Hz, 2H), 6.62 (d, J = 4.0 Hz, 1H), 6.50 (t, J = 2.3 Hz, 1H), 3.83 (s, 6H). M/Z: 418.10, M+1: 418.90, tR= 1.63 min (System 1).

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Evotec (UK) Ltd.; Mills, Matthew; McCarthy, Clive; EP2924038; (2015); A1;,
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Application of 1836-62-0, These common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, 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.

General procedure: A solution of 2-phenoxyethylamine (1.31 mL, 10 mmol) in methanol (10 mL) was added to a solution of triethylamine(Et3N) (2.76 mL, 20 mmol) in methanol (10 mL) at 0 C. A solution of 2-chloropyridine (3.80 mL, 40 mmol) in methanol(10 mL) was then added at 0 C under N2. After being stirred for 30 min, the reaction mixture was heated to 25 C and stirred for 3 days. Then, the solvent was evaporated under reduced pressure to afford a yellow solid L1 washed with methanol and dried under vacuum.

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Jun; Liu, Jinyi; Chen, Liduo; Lan, Tianyu; Wang, Libo; Transition Metal Chemistry; vol. 44; 7; (2019); p. 681 – 688;,
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Application of 126-38-5,Some common heterocyclic compound, 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, molecular formula is C5H11BrO2, 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 sealed flask, 3,6-dichloro-4-methylpyridazine (27 g, 161 mmol) was suspended in aqueous ammonia (25%, 300 mL). The reaction mixture was heated at 110 C for 48 hours (turned into solution after 1 hour). After cooling to room temperature, the reaction was poured into CH2C12, and the organic phase was separated, dried over Na2SO4, and concentrated under vacuum, to give 22.4 g of 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl-pyridazin-3-amine as a mixture of regioisomers which were used directly in the next step. The mixture of regioisomers 6-chloro-4-methyl-pyridazin-3-amine and 6-chloro-5-methyl- pyridazin-3-amine (22.4 g) was suspended in 2-propanol (300 mL). 1-bromo-2,2- dimethoxypropane (36.0 g, 26.6 mL, 193 mmol, 1.2 eq.) and PPTS (2.96 g, 11.6 mmol, 0.0725 eq.) were added, and the resulting solution was heated at 105C overnight. The solvent wasremoved in vacuo and the residue was taken up in CH2C12 and washed with NaHCO3. The organic phases were dried over Na2SO4, concentrated in vacuo and the crude light brown solid was chromatographed (EtOAc / Heptane 1/2 -1/1) to give separately 6.1 g of 6-chloro-2,8- dimethyl-imidazo[1,2-b]pyridazine MS m/z 182.1 [M+H] (21%) as a white solid and 5.9 g of 6- chloro-2,7-dimethyl-imidazo[1,2-b]pyridazine MS m/z 182.1 [M+H] (20%) as a white solid.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ALSENZ, Jochem; GRASSMANN, Olaf; KUEHL, Peter; METZGER, Friedrich; MCCARTHY, Kathleen Dorothy; MORAWSKI VIANNA, Eduardo Paulo; WOODHOUSE, Marvin Lloyd; (130 pag.)WO2017/80967; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22236-08-4, name is 3-(Difluoromethoxy)aniline, belongs to ethers-buliding-blocks 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 22236-08-4, HPLC of Formula: C7H7F2NO

Intermediate 2 rac- Allyl [3 -(4-chloro-3 -methylphenyl)- 1 – {N’ -cyano-N- [3 -(difluoromethoxy)phenyl] caxbamimidoyl } – 4.5-dihydro- 1 //-pyrazol-4-yl j carbamate To a stirred solution of m-difluoromethoxyaniline, 6.55 g (41.2 mmol) in tetrahydrofuran (60 mL) at – 70 to -60 C was added n-butyllithium, 21 mL (41.2 mmol, 2 M in hexanes) dropwise. The mixture was stirred for 1 hour at this temperature, at which time a solution of n/< -phenyl -4- { [(allyloxy)carbonyl]amino } -3 -(4-chioro-3 -methylphenyl)-N-cyano-4,5-dihydro- 1 H-pyrazoie- 1 - carboximidate (intermediate 10), 6.00 g (13.7 mmol) in tetrahydrofuran (100 mL) was added dropwise maintaining the temperature below -60 C. The reaction mixture was stirred for 2 hours and was then poured into saturated aqueous ammonium chloride solution (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine (200 mL), dried over magnesium sulfate and concentrated to give a yellow solid. The solid was slurried with diethyl ether (50 mL) and dried to give rac-allyl [3-(4-chloro-3-methylphenyl)-l-{N'-cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl}- 4,5-dihydro- l/ -pyrazol-4-yl] carbamate, 6.20 g (90%) as a white solid. NMR (400 MHz, DMSO-d, ): delta [ppm] = 2.32 (s, 3H), 4.06 (dd, 1H), 4.35-4.53 (m, 311 ). 5.11 (d, 1H), 5.17 (dd, 1H), 5.49-5.60 (m, 1H), 5.84 (ddt, 1H), 6.98 (dd, 1H), 7.12-7.27 (m, 3H), 7.35-7.42 (m, 1H) 7.51 (d, 1H), 7.69 (dd, 1H), 7.83 (d, 1H), 8.15 (d, 1H), 9.70 (br s, 1H). LCMS (method 3): Rt = 1.79 min MS (ESI): [M + H j = 503.2 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, 3-(Difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see. Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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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. 589-10-6, name is (2-Bromoethoxy)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H9BrO

Alternate synthesis: l-(2-phenoxyethyl)-lH-pyrazole-4-carbaldehydeSodium hydride (60%>, 6.3 g, 1.0 eq) was added to a solution of lH-pyrazole-4- carbaldehyde (15 g, 156 mmol) in DMF (150 ml) at 0C. The mixture was allowed to warm and was stirred at room temperature. (2-Bromoethoxy)benzene (30.2 g, 1 eq) was then added and the resulting mixture was stirred overnight at room temperature. It was quenched by addition of aqueous ammonium chloride, diluted with water and extracted with EtOAc. The combined organic layers were dried over Na2S04, filtered, and concentrated. The residue was purified by column chromatography using a hexane/EtOAc gradient (10: 1 to 0: 100). Pure fractions were combined and evaporated under reduced pressure to yield l-(2-phenoxyethyl)-lH-pyrazole-4-carbaldehyde (24 g, 71%).

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; REPLIGEN CORPORATION; JACQUES, Vincent; RUSCHE, James R.; PEET, Norton P.; SINGH, Jasbir; WO2012/118782; (2012); A1;,
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Reference of 74137-36-3, These common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 2-To a solution of R-27b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford R-28.

The synthetic route of 74137-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billedeau, Roland Joseph; Sweeney, Zachary Kevin; US2009/170856; (2009); A1;,
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Application of 645-36-3, 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 645-36-3 as follows.

In a 100 mL flask, 3-fluoro-4-((phenoxycarbonyl)amino)benzoic acid methyl ester was added(3. 3 g, 11. 4 mmol, 1 Oeq.),2, 2-diethoxyethanamine (1.28 g, 13. 68 mmol, 1.2 eq.),piperidine (1.4 ml, 17.1 mmol, 1.5 eq.)And 6 mL of N, N-dimethylformamide,95 degrees Celsius heating and stirring 15h.To the reaction solution was added lmL concentrated hydrochloric acid for quenching,Then 40 mL of water was added to extract with ethyl acetate (40 X 3)The organic phases were combined,The organic phase was washed with saturated brine (40 mL)Dried over anhydrous Na2S04, filtered, and the organic solvent was distilled off under reduced pressure to give a brown liquid (3.3 g, Y = 89%)

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hubei Xinxiwang Bio-technology Co.,Ltd; xiao, hong; (19 pag.)CN105294567; (2016); A;,
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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. 126-38-5, name is 1-Bromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H11BrO2

Step B: To a suspension 5-chloro-3-(difluoromethyl)pyrazin-2-amine (0.5 g, 2.8 mmol) in iPrOH (10 ml) was added l-bromo-2,2-dimethoxypropane (1.1 ml, 8.4 mmol), pyridinium para-toluene sulfonic acid (0.1 g, 0.3 mmol) and the mixture heated to 65C in a sealed tube for 18h. The reaction was diluted with DCM, washed with saturated sodium hydrogen carbonate solution, dried (Na2S04) and concentrated. Purification by flash column chromatography on silica gel (EtOAc: Hept 1:4- 1:0) afforded the titled product as a brown powder (0.20 g, 40%). MS (m/e): 218.1. (M+H+, CI)

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 126-38-5.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GREEN, Luke; PINARD, Emmanuel; RATNI, Hasane; WILLIAMSON, Patrick; (95 pag.)WO2015/197503; (2015); A1;,
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Reference of 6851-80-5,Some common heterocyclic compound, 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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.

General procedure: To a mixture of the corresponding secondary amines 7a-d (0.77mmol), anhydrous K2CO3 (106.2mg, 0.77mmol) and KI (8.6mg, 0.052mmol) in CH3CN (10mL) were added the appropriate intermediates 12-14 (0.60mmol). The reaction mixture was warmed to 60-65C and stirred for 12-15h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Water (30mL) was added to the residue and the mixture was extracted with dichloromethane (30mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixture of CH2Cl2/CH3OH as eluent, obtaining the corresponding 7-O-MOM-4?-O-modified genistein derivatives.

The synthetic route of 6851-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qiang, Xiaoming; Sang, Zhipei; Yuan, Wen; Li, Yan; Liu, Qiang; Bai, Ping; Shi, Yikun; Ang, Wei; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 76; (2014); p. 314 – 331;,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3-Fluoro-4-methoxyaniline

To a sample of 113 (1.011 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solutionof 3-fluoro-p-anisidine (0.541 g, 3.8 mmol) in acetone (10 mL) followed by additionof NaOH (1.52 mL, 2.5 N, 3.8 mmol) and water (3 mL). The reaction mixture was allowed to stir at reflux for about 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane ; the combined organic layers were washed with brine solution and dried over potassium carbonate. The sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (silica gel, 70: 30 hexanes : ethyl acetate) yielded light yellow solid compound 114 (0.581 g, 42percent), mp98 C ; TLC (silica gel, 30: 70 ethyl acetate: hexanes), Rf 0.36 ; MS (ESI):m/z 369 (39.1), 368 (22.1), 367 (M+H, 100), 273 (3.2), 271 (10.7). Compound 115 was obtained as a by-product (0.159 g) via column chromatography (silica gel, 70: 30 hexanes : ethyl acetate), mp181 C ; TLC (silica gel, 30: 70 ethyl acetate: hexanes), Rf 0.17 ; MS (ESI): nez 472 (M+H, 100), 261 (1.5).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
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