Tag: M.W=200-300

Synthetic Route of 92248-06-1,Some common heterocyclic compound, 92248-06-1, name is Bis(3-methoxyphenyl)amine, molecular formula is C14H15NO2, 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,Adding 2,2′-dibromo-9,9′-spirobifluorene (0.7 g, 1.48 mmol),Bis (3-methoxyphenyl) amine (1.01 g, 4.44 mmol),Palladium acetate (18mg, 0.082mmol),Cesium carbonate (1.74g, 5.33mmol)And tri-tert-butylphosphine (0.038mL, 0.15mmol) in toluene(10mL) mixed well in the solution,Heat and stir at 110 C for 20 hours.After cooling to room temperature,The reaction was quenched with a saturated ammonium chloride solution.The aqueous layer was extracted three times with ethyl acetate,Use up the combined organic phasesAnd washed with aqueous sodium chloride.After the organic phase was dried over anhydrous sodium sulfate,The solvent was evaporated to dryness under reduced pressure,The obtained product was further purified by silica gel column chromatography,Petroleum ether / ethyl acetate (10: 1, v / v) was used as the eluent.Get pure product,As a white solid.Yield: 95% (1.08 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Bis(3-methoxyphenyl)amine, its application will become more common.

Reference:
Patent; Nanjing Tech University; Hang Xiaochun; Qian Chunyue; Huang Wei; Shen Kang; Qin Tianshi; (57 pag.)CN110790629; (2020); A;,
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Adding a certain compound to certain chemical reactions, such as: 6358-77-6, name is 5-Bromo-2-methoxyaniline, 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 6358-77-6, name: 5-Bromo-2-methoxyaniline

N, N-DIISOPROPYLETHYLAMINE (13.49 ml, 77.4 mmol) and methyl bromoacetate (0.95 eq, 49.0 mmol) were added to a solution of 5-bromo-2-methoxyaniline (1 eq, 51.6 mmol) in anhydrous DMF (100 ml) under nitrogen. The solution was heated for 16 hours at 60 C before cooling to ambient temperature. DMF was removed under reduced pressure. The residue was dissolved in 500 ml of DCM, washed with 2 x 200 ml of water, was dried over sodium sulfate and was filtered and concentrated under reduced pressure. The title compound was precipitated from DCM/hexanes as an off-white, brownish solid (10.34 G)

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/41799; (2004); A1;,
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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. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

[0403] To a solution of 5-acetyl-N-(2,6-diethylphenyl)-1-methyl-1H-pyrazole-3-carboxamide (0.013 g, 0.043 mmol) in DMF (1.5 mL), N,N-dimethylformamide di-tertbutyl acetal (0.0.63 mL, 0.650 mmol) was added. The mixture was stirred at 80 C. for 2 h. The reaction was diluted with water, extracted with AcOEt (2×20 mL). The organic fractions were combined, dried over Na2SO4, filtered, and concentrated in vacuo and the residue used without any further purification. (0.017 g, 78% yield). [0404] 1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (s, 1H), 7.71 (d, J=12.33 Hz, 1H), 7.36 (s, 1H), 7.21 (t, J=7.60 Hz, 1H), 7.12 (d, J=7.60 Hz, 2H), 5.75 (d, J=12.33 Hz, 1H), 4.18 (s, 3H), 3.16 (s, 3H), 2.92 (s, 3H), 2.52 (q, J=7.57 Hz, 4H), 1.09 (t, J=7.57 Hz, 6H) [0405] HRMS (ESI) calcd for C20H27N4O2 [M+H]+ 355.2129. found 355.2133.

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; Casuscelli, Francesco; Brasca, Maria Gabriella; Caldarelli, Marina; Cervi, Giovanni; Disingrini, Teresa; Quartieri, Francesca; US2014/51708; (2014); A1;,
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Synthetic Route of 17061-62-0,Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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.

N,N-bis(4-methoxybenzyl)ethanesulfonamide, Example 12.0. To a solution of bis(4-methoxybenzyl)amine 12.01 (900 g, 3.49 mol, 1 eq) in DCM (9 L) was added TEA (634 mL, 4.55 mol, 1.3 eq), followed by dropwise addition of ethanesulfonyl chloride (399 mL, 4.19 mol, 1.2 eq). (The internal temperature was kept between 5-10 C during the addition of the ethane sulfonyl chloride). Once the addition was complete, the cooling bath was removed. After 1.5 h, TLC showed complete loss of starting material. The reaction was quenched by the addition of water (4 L) to the reaction mixture. The layers were separated and the aqueous layer extracted with DCM (2 x 2 L). The combined organic layers were washed with brine (2x 1 L), dried over Na2SO4, and concentrated in vacuo. The material thus obtained was adsorbed onto a plug of silica gel and purified by chromatography (silica gel (60-120 mesh) eluting with a gradient of 10- 80% EtOAc in hexanes) to provide the title compound 12.0 (1125 g, 3.22 mol, 92%) as white solid. ?H-NMR (400 MHz, CDC13) 7.23 (dd, J= 2.08, 6.62 Hz, 4H), 6.90 (dd, J= 2.12, 6.60 Hz, 4H), 4.29 (s, 4H), 3.83 (s, 6H), 2.92 (q, J 7.40 Hz, 2H), 1.33 (t, J 7.40 Hz, 3H). GC-MS (ESI pos. ion) m/z: 372.2 (M+Na).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Bis(4-methoxybenzyl)amine, its application will become more common.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
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Reference of 6943-97-1,Some common heterocyclic compound, 6943-97-1, name is 1-(3-Bromopropyl)-3-methoxybenzene, molecular formula is C10H13BrO, 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 flask containing solution of Mg turnings (271 mg, 11.31 mmol) in THF (10 mL) and a few crystals of iodine under nitrogen was added a solution of compound 15 (2.42 g, 11.31 mmol) in THF (15 mL) drop wise and reflux for 3 hrs. After 3 hrs the majority of the Mg had dissolved and a clear grayish colored solution had formed. The solution was cooled to 0 C and a solution of compound 16 (1.5 g, 7.07 mmol) in THF was added drop wise. The mixture was allowed to warm slowly to rt and reaction was monitored by tlc. Once the starting material is consumed the reaction mixture was quenched by saturated aqueous NH4Cl solution (30 mL). The reaction mixture was extracted with EtOAc (20 mL x 3) and layer was separated and washed with brine and dried over MgSO4. Removal of solvent and drying under vacuum provided the crude product that was separated by flash chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(3-Bromopropyl)-3-methoxybenzene, its application will become more common.

Reference:
Article; Asim, Muhammad; Klonowska, Daria; Choueiri, Christine; Korobkov, Ilia; Carlson, Kathryn E.; Katzenellenbogen, John A.; Durst, Tony; Bioorganic and Medicinal Chemistry Letters; vol. 22; 11; (2012); p. 3713 – 3717;,
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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. 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,2-Dibromo-4,5-dimethoxybenzene

a) Preparation of 4′,5′-Dimethoxy-[1,1′:2′,1″-terphenyl]-4,4″-dicarbonitrile A flask containing 4,5-dibromoveratrole (407 mg, 1.375 mmol), 4-cyanophenylboronic acid (606 mg, 4.125 mmol), Pd(PPh3)4 (159 mg, 0.1375 mmol), and Na2CO3 (729 mg, 6.875 mmol) was degassed and dioxane (6 mL) and H2O (3 mL) were added. Reaction was refluxed at 102 C. overnight then cooled to RT and diluted with EtOAc. Solution was washed with saturated NaHCO3 solution followed by brine and organic layer was collected, dried over Na2SO4, and concentrated. Chromatography using ISCO max gradient 50% EtOAc/hexane yielded product as a light yellow solid (467 mg, quantitative); 1H NMR (400 MHz) (CDCl3) delta 7.46-7.44 (m, 4H), 7.14-7.12 (m, 4H), 6.83 (s, 2H), 3.89 (s, 6H); 13C NMR (100 MHz) (CDCl3) delta 149.4, 145.6, 132.0, 131.3, 130.6, 118.7, 113.5, 110.6, 56.2.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LaVoie, Edmond J.; Arnold, Eddy; Bauman, Joseph D.; Kerrigan, John E.; Parhi, Ajit K.; Das, Kalyan; Kelley, Cody; Patel, Dishaben V.; US2015/322022; (2015); A1;,
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Related Products of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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 4-bromo-2-methoxyaniline (208 mg, 1.03 mmol), 1 ,2,4-triazole (80 mg, 1.13 mmol), Cs2CO3 (0.67 g, 2.06 mmol) and Cul (20 mg, 0.103 mmol) in DMF was heated at 110 oC for 20 h. Further portions of 1,2,4-triazole (0.1 g, 1.44 mmol), Cs2CO3 (0.67 g, 2.06 mmol) and Cul (0.1 g, 0.52 mmol) were added and the mixturewas heated a further 72 h at 110 oC. The mixture was cooled, diluted with ethyl acetate (20 mL) and washed with water (2 x 20 mL). The combined aqueous washes were reextracted with ethyl acetate (20 mL). The combined organics were passed through a phase separation cartridge and the solvent removed under reduced pressure. Purification of the residue via silica gel column chromatography (0-100% ethyl acetate isohexane)gave 2-methoxy-4-(1H-1,2,4-triazol-1-yl)aniline as a light red solid (92 mg, 47%). ?H NMR (400 MHz, CDC13): oe 8.41 (s, 1H); 8.05 (s, 1H); 7.11 (d, J = 2.3, 1H); 6.99 (dd, J = 8.3, 2.3, 1H); 6.74 (d, J = 8.3, 1H); 3.97 (s, 2H); 3.92 (s, 3H).

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; CHAMBERS, Mark; CHAN, Bryan K.; ESTRADA, Anthony; SWEENEY, Zachary Kevin; WO2013/79495; (2013); A1;,
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Synthetic Route of 944317-92-4, 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. 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 500 mL dry flask was charged with 2-bromo-5-fluoro-4-isopropylanisole (compound of formula 4, Scheme 3) (24.6 g, 0.1 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri-isopropylborate (32 mL, 0.14 mol) was added. The mixture was cooled to -80 C. Then 10 M n-BuLi in hexanes (12.5 mL, 0.125 mol) was added slowly, maintaining a temperature below -55C. Thirty minutes after completion of the n-BuLi addition, the reaction was warmed to -35C and quenched into 3 M H2S04 solution (75 mL, 0.225 mol). DIPE (200 mL) was added to the mixture to dilute the organic layer. The mixture was stirred (15 min) and the aqueous layerwas cut away. The organic layerwas washed with 3.0 M H2S04 (75 mL). The organic phase was extracted three times with 1 M NaOH (200 mL first and then 50 mL and 50 mL). The three NaOH extractions were combined, diluted with 2-propanol (85 mL), and cooled to 15 “C. Then the solution was slowly acidified to pH ~ 2 using 3 M H2SO4 (70 mL) while maintaining temperature at 15-20 C. The resulting slurry was stirred for 1 hour and then filtered. The filter cake was washed with water (3 x 30 mL) and dried under an air flow for 1 day. The filtered solid was placed in an oven under vacuum at 50 C for 2-3 days to decompose a diaryl impurity and to dry the solid. The white crystalline solid was isolated to yield boronic acid of formula 5 (Scheme 3) (19.23 g, 91 %): mp 100-102 C; H NMR (CDCI3) delta 1.25 (d, J = 6.9 Hz, 6H), 3.17 (sept, J = 6.9 Hz, 1 H), 3.88 (s, 3H), 5.83 (S, 2H), 6.59 (d, J = 12 4 Hz, 1 H), 7.72 (d, J = 6.6 Hz, 1 H). The impurity 5-ethyl-4-fluoro-2-methoxyphenylboronic acid (-4%), which is formed from 1-bromo-5-ethyl-4-fluoro- 2-methoxybenzene (BrMET) present in the starting material under the conditions described in Step 4, was detected in the product.

The synthetic route of 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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Related Products of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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: An autoclave was filled with catalyst (1 molpercent based on the molar amount of amine), flushed with argon and topped up with a solution of amine (0.1 mol) and orthocarboxylic acid ester (0.11-0.3mol) in 10 ml of methanol (or ethanol) and 0.5 ml of a 0.2 M solution of anhydrous ptoluenesulphonic acid in methanol (or ethanol). The mixture was heated to 120°C and hydrogen was injected to 40 bar and then the mixture was stirred at a constant pressure until hydrogen absorption could no longer be detected (0.2 – 6 h). After being filtered off from the catalyst, the filtrate was distilled.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EVONIK DEGUSSA GMBH; KADYROV, Renat; (19 pag.)WO2017/133913; (2017); A1;,
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Reference of 588-96-5, 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. 588-96-5 name is p-Bromophenetole, 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.

Example I.1 (S)-N-(1-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide 147 mg (0.60 mmol) (S)-N-[1-(Piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) are added to a mixture of 100 mg (0.50 mmol) 1-bromo-4-ethoxy-benzene, 197 mg (2.00 mmol) sodium tert-butyrat, 59 mg (0.20 mmol) 2-(di-tert-butylphosphino)biphenyl and 46 mg (0.05 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 2.0 mL 1,4-dioxane. The mixture is stirred for 4 h at 45 C. After that time, the mixture is filtered over celite. The solvent is removed in vacuo from the filtrate. The residue is purified by HPLC (column: Waters XBridge 5 muM; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product. C23H30N2O2 (M=366.5 g/mol) ESI-MS: 367 [M+H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, p-Bromophenetole, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/157425; (2012); A1;,
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