Author: Jessica.F

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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, A new synthetic method of this compound is introduced below., Quality Control of 3,5-Dimethoxyphenylacetylene

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 ¡Á 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Formula 2 for the general method in accordance with, 1:1 t-BuOH/H2O (3 mL) in a compound 7a (95.8 mg, 300 mumol), 1-ethynyl -3,5-dimethoxybenzene (121 mg, 750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. Using ascorbate (60.0 mg, 300 mumol) was prepared in the desired compound. After stirring at room temperature the reaction mixture for 2 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 40: 1 CH2Cl2 / MeOH) to compound 2a using a was obtained as a brown solid (138 mg, 98%).

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

Reference:
Patent; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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Electric Literature of 60789-54-0, These common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, 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.

EXAMPLE 231 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (1.1 g) as starting compound, potassium carbonate (1.5 g) and 4-benzyloxybutyl bromide (1.0 g) were reacted and treated in the same manner as in Example 168 to give 0.32 g of 4-amino-5-chloro-2-methoxy-N-((1-(4-benzyloxybutyl)piperidin-4-yl)methyl)benzamide. 1 H-NMR (CDCl3,ppm) delta: 1.40-1.81(9 H,m), 2.82(2 H,t), 2.98(2 H,t), 3.20(2 H,t), 3.44(4 H,m), 3.82(3 H,s), 4.45(3 H,s), 5.93(2 H,s), 6.48(1 H,s), 7.33-7.45(5 H,m), 7.66(1 H,s), 8.00(1 H,t)

The synthetic route of 60789-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yoshitomi Pharmaceutical Industries, Ltd.; US5864039; (1999); A;,
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Related Products of 5467-58-3,Some common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, molecular formula is C11H9BrO, 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.

Under a nitrogen atmosphere, into a 250 mL three-necked flask equipped with a magnetic stirrer, a thermometer, and a condenser, 6.6 g (27.9 mmol) of 1-bromo-4-methoxynaphthalene and 12.0 g (36.3 mmol) of 4- were added. Nitrophenyl-2-amino-9,9-dimethylhydrazine,10.6g (167.4mmol) of copper powder, 23.1g (167.4mmol) of potassium carbonate, 7.4g (27.9mmol) of 18-crown-6, then add 57.2ml of o-dichlorobenzene, react at 170 C for 20h; Filtration, distillation of o-dichlorobenzene under reduced pressure, and the obtained crude product was ethanolRecrystallization with N,N-dimethylacetamide (V:V = 1:2.7),4-nitrophenyl-4′-methoxynaphthyl-2-amino-9,9-dimethylfluorene 10.2 g, yield 75%

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-4-methoxynaphthalene, its application will become more common.

Reference:
Patent; Jilin University; Chen Chunhai; Su Kaixin; Wang Daming; Sun Ningwei; Zhou Hongwei; Zhao Xiaogang; (23 pag.)CN108912003; (2018); A;,
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Synthetic Route of 41365-75-7, 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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-(chloromethyl)-benzoyl chloride (1.17 g, 6.21 mmol) in DCM (10 mE) was added a solution of 3,3-diethoxypropan-1-amine (0.914 g, 6.21 mmol) and triethylamine (1.04 mE, 7.77 mmol) in DCM (10 mE). The reaction mixture was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure and the residue dissolved in ethyl acetate. The organic phase was washed with 1 M aqueous sodium hydroxide, brine and dried over anhydrous magnesium sulfate and the filtrate was evaporated under reduced pressure to afford the title compound(1.83 g, 99%). 1H NMR (400 MHz, DMSO-d5); oe 8.45 (dd, J=5.5,5.5 Hz, 1H), 7.83 (d, J=8.4 Hz, 2H), 7.52 (d, J=8.3 Hz, 2H),4.81 (s, 2H), 4.56 (dd, J=5.5, 5.5 Hz, 1H), 3.59 (ddd, J=7.1,9.5, 14.1 Hz, 2H), 3.45 (ddd, J=7.1, 9.5, 14.1 Hz, 2H), 3.29 (dd, J=6.0, 7.4 Hz, 2H), 1.79 (dd, J=6.4, 13.6 Hz, 2H), 1.12 (dd, J=7.0, 7.0 Hz, 6H).

The chemical industry reduces the impact on the environment during synthesis 1-Amino-3,3-diethoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; RANCATI, Fabio; RIZZI, Andrea; CARZANIGA, Laura; LINNEY, Ian; KNIGHT, Chris; SCHMIDT, Wolfgang; (176 pag.)US2016/235734; (2016); A1;,
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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. 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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