Month: August 2021

Reference of 54149-17-6,Some common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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.

3-(2-(2-Methoxyethoxy)ethoxy)prop-1-yne (9) To a stirred suspension of sodium hydride (3.12 g, 78.0 mmol) in THF (100 mL) cooled to 5 C. in an ice-bath was added a solution of propargyl alcohol (4.60 g, 78.0 mmol) in THF (20 mL) drop-wise. The mixture was stirred at 5 C. for 30 min and was then allowed to warm to RT and treated dropwise with 1-bromo-2-(2-methoxyethoxy)ethane (7.00 mL, 52.0 mmol). The reaction mixture was stirred at RT for 16 hr and was then, diluted with water (100 mL) and extracted with diethyl ether (2*100 mL). The combined organic extracts were dried, filtered and evaporated in vacuo. The residue was purified by flash column chromatography, eluting with 30% EtOAc in heptane, to afford the title compound (9) (250 mg, 9%) as a colourless oil: 1H NMR (500 MHz, MeOD) delta: 4.18 (2H, d), 3.66-3.69 (2H, m), 3.60-3.66 (4H, m), 3.52-3.56 (2H, m), 3.36 (3H, s), 2.84 (1H, t).

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-methoxyethoxy)ethane, its application will become more common.

Reference:
Patent; King-Underwood, John; Ito, Kazuhlro; Murray, Peter John; Hardy, George; Brookfield, Frederick Arthur; Brown, Christopher John; US2012/208799; (2012); A1;,
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Synthetic Route of 101-55-3,Some common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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.

The (S) -A40.2g (0.64mmol), 4- phenoxy-bromobenzene 0.24g (0.96mmol, 1.5eq.), Palladium acetate 0.013g (0.06mmol, 0.1eq.), BINAP0.037g (0.06mmol after, 0.1eq.), cesium carbonate 0.52g (1.6mmol, 2.5eq.) swap argon, DMF (4mL), the reaction 100 8 h, concentrated after adding saturated brine, extracted with methylene chloride and dried, Biotage silica gel column chromatography (petroleum ether / ethyl acetate = 28%) to give a pale yellow solid A70.27g, yield 87%.

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-phenoxybenzene, its application will become more common.

Reference:
Patent; Nanjing Yong Shan Biological Technology Co., Ltd.; Wang Yazhou; Jin Qiu; Tang Feng; Huang Wei; Hua Yulin; (10 pag.)CN103113375; (2017); B;,
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Related Products of 171290-52-1, These common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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 solution of methoxy ethynylbenzenes (20 mmol) and methoxy substituted aryl iodide (22 mmol) in isopropylamine (120 ml) were added Pd(PPH3)2Cl2 (0.2 mmol) and CuI (0.4 mmol). The reaction mixture was stirred at ambient temperature for 6 hours under a slow stream of nitrogen. The reaction mixture was filtered and the residues were washed with ethyl acetate and the solvent evaporated from the combined filtrates. The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (9:1) as an eluent to give methoxytolans.

Statistics shows that 3,5-Dimethoxyphenylacetylene is playing an increasingly important role. we look forward to future research findings about 171290-52-1.

Reference:
Patent; KENT STATE UNIVERSITY; SUMMA HEALTH SYSTEM; WO2008/157745; (2008); 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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Bromo-4-fluoro-2-methoxybenzene

A mixture of 1 -bromo-4-fluoro-2-methoxybenzene (CAS No. [450-88-4]; 10.0 g, 48.8 mmol) in concentrated sulfuric acid (50 ml.) was cooled to 0 C and treated dropwise with a freshly prepared mixture of fuming nitric acid (1.05 eq., 2.1 ml_, 51 mmol) and concentrated sulfuric acid (1.85 eq., 4.8 ml_, 90 mmol). The reaction mixture was stirred at 0 C for 30 minutes and poured in small portions on ice water. The formed precipitate was filtered off, washed with cold water and kept. The filtrate was extracted with ethyl acetate and the organic layer combined with the isolated precipitation. The organic layer was dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (Si02-hexane/ ethyl acetate) to give the title compound (5.88 g, 44%). 1H-NM (400MHz, DMSO-de): delta [ppm] = 4.00 (s, 3H), 7.44 (d, 1 H), 8.40 (d, 1 H).UPLC- UPLC-MS (ESI-): [M – H]” = 248/250; Rt = 1.17 min (Br isotope pattern; Method E).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; PANKNIN, Olaf; ZIMMERMANN, Katja; NEUHAUS, Roland; (162 pag.)WO2017/5674; (2017); A1;,
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Synthetic Route of 1116-77-4, 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. 1116-77-4, name is 4,4-Diethoxy-N,N-dimethyl-1-butanamine, This compound has unique chemical properties. The synthetic route is as follows.

Example 9 (0448) Synthesis of N-(4-(2-acetoxy-4-methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan- 1 -aminium bromide (0449) In a N2 purged 20mL weighed glass vial with stir bar is added 1 .5g (0.004mol, 1 .0 eq) of AcO-Bzp-OMe-CH2-Br prepared in Example 7 and 8 mL ethyl acetate to give a clear solution on stirring for 20mins at RT. 2.06 g 4,4-Diethoxy-N,N-dimethyl-1 -butanamine (0450) (NNDMABADEA, from TCI-America) (0.01 mol, 2.5 eq) is slowly added to the reaction solution with stirring. A precipitate is soon formed and gradually thickenes with stirring over 30- 60minutes. The reaction mixture is stirred at RT overnight. The stirring is stopped and the mixture is allowed to stand for an hour. The mixture is filtered through a coarse filter frit at around 850mbar. The precipitate is washed five times with 10ml_ ethyl acetate. The precipitate is transferred into a 10OmL rb flask with about 18ml of Dl Water. The residual organics are removed under reduced pressure to give a clear solution. The solution is filtered through a Whatman1 (1 1 urn) filter paper to give a clear solution with neutral pH, that is frozen and lyophilized to give a off white solid which is confirmed to be N-(4-(2-acetoxy-4- methoxybenzoyl)benzyl)-4,4-diethoxy-N,N-dimethylbutan-1 -aminium bromide and is stored under dry N2 in desiccator.

The chemical industry reduces the impact on the environment during synthesis 4,4-Diethoxy-N,N-dimethyl-1-butanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; CHANG, Frank; DESOUSA, Ryan; HOLLAND, Troy Vernon; LAREDO, Walter R.; (68 pag.)WO2017/93835; (2017); A1;,
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Electric Literature of 1758-46-9, 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. 1758-46-9, name is 2-Phenoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

d) (4-Methyl-7-trifluoromethyl-3,4-dihydro-quinazolin-2-yl)-(2-phenoxy-ethyl)-amine 4-Methyl-2-methylsulfanyl-7-trifluoromethyl-3,4-dihydro-quinazoline hydroiodide (116 mg, 0.30 mmol) and 2-phenoxyethyl amine (126 mg, 0.9 mmol) were dissolved in acetonitrile (0.9 ml) and heated to 170° C. in a sealed tube in a microwave oven for 30 minutes. After cooling the reaction was treated with 1N aqueous sodium hydroxide solution, methylene chloride and 5 to 7 drops of 30percent aqueous hydrogen peroxide solution. After the reaction has ceased the reaction was diluted with little water and the precipitated product was filtered off, washed with water, dried in vacuo to yield the title compound as a white solid (104 mg, 94percent). (MS: m/e=350.2, 351.1 [M+H+]). 1H NMR (CDCl3): delta 1.25 (3H, d), 3.58 (2H, m), 4.05 (2H, t), 4.55 (1H, q), 6.08 (1H, bt), 6.37 (1H, s), 6.91-7.01 (5H, m), 7.11 (1H, d), 7.29 (2H, t).

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

Reference:
Patent; Alanine, Alexander; Gobbi, Luca Claudio; Kolczewski, Sabine; Luebbers, Thomas; Peters, Jens-Uwe; Steward, Lucinda; US2006/252779; (2006); A1;,
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Related Products of 62257-15-2, 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. 62257-15-2 name is 2-Fluoro-5-methoxyaniline, 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.

2-Fluoro-5-methoxyaniline (2.32 g, 16.4 mmol) was dissolved in acetic acid (11.6 mL) and water (1.16 mL), then a solution of potassium cyanate (1.33 g, 16.4 mmol) in water (1 mL) was added dropwise and the mixture was stirred at rt for 3 h. The reaction mixture was filtered, the filter cake was washed with water and ether and was dried under vacuum to give the title compound as an off-white solid. [M+H] = 185.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; DART NEUROSCIENCE, LLC; SANTORA, Vincent, John; CHEN, Mi; CHUNG, DeMichael; (377 pag.)WO2019/14305; (2019); A1;,
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Electric Literature of 52411-34-4,Some common heterocyclic compound, 52411-34-4, name is 1,2-Bis(o-aminophenoxy)ethane, molecular formula is C14H16N2O2, 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.

Compound 3 (2.44 g, 0.01 mol) was dissolved in MeCN(10 mL), then (i-Pr)2NEt (6 mL) and methyl bromoacetate (3 mL) were added to the mixture with stirring. The reaction mixture was refluxed for 24 h. After the reaction, the mixture was cooled down, poured into EtOAc (20mL), and filtered to remove the generated white solid. The combined EtOAc filtrates were concentrated in vacuo to give an oily solid, then adding a little methanol, white solid was generated, filtered, air dried and recrystallized in MeOH to give white solid 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Bis(o-aminophenoxy)ethane, its application will become more common.

Reference:
Article; Cheng, Zhao; Yang, Bingqin; Yang, Meipan; Zhang, Binglin; Journal of the Brazilian Chemical Society; vol. 25; 1; (2014); p. 112 – 118;,
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These common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-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. Recommanded Product: 261762-35-0

A 100-mL round-bottom flask charged with Pd2dba3 (69 mg, 0.075 mmol), BINAP (112 mg, 0.18 mmol), and NaOt_Bu (650 mg, 6.5 mmol) was degassed and filled with N2. THF (20 mL) was added, followed by a solution 5-bromo-l,2-difluoro-3-methoxybenzene (1.1 g, 5 mmol) and l-(2,5-dimethoxyphenyl)ethanone (1.08 g, 6 mmol) in THF (10 mL). The resulting mixture was heated at 70 C for 16 h. Water (30 mL) was added, and the mixture was extracted with ether (3 x 50 mL). The combined organics were dried over anhydrous Na2S04, filtered, and concentrated to give the crude product, which was purified by column chromatography on silica gel (eluting with petroleum ether/ethyl acetate = 80/1 ~ 40/1) to give 2-(3,4-difluoro-5- methoxyphenyl)-l-(2,5-dimethoxyphenyl)ethanone (0.4 g) as a light yellow solid. ¾ NMR (CDCI3): delta 7.24 (d, 1H), 7.04 (dd, 1H), 6.92 (d, 1H), 6.68-6.61 (m, 2H), 4.23 (s, 2H), 3.90 (s, 3H), 3.87 (s, 3H), 3.78 (s, 3H); LCMS: 323 (M+H)+.

The synthetic route of 5-Bromo-1,2-difluoro-3-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
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Synthetic Route of 62257-15-2, 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 62257-15-2 as follows.

Example 9: Intermediate 9~ 8-fluoro-5-methoxy-2-methylquinoline[0235] 8-Fluoro-5-methoxy-2-methylquinoline was synthesized from 2-fluoro-5-methoxyaniline (30.0 g, 213 mmol) according to the procedures described above for 8-chloro-5-methoxy-2- methylquinoline hydrochloride (Intermediate 1 , Step 1) with the following change: The hydrochloride salt was dissolved in dichloromethane (400 mL) and the pH of the resulting solution was adjusted to 8-9 with saturated aqueous potassium carbonate solution. The resulting mixture was extracted with dichloromethane, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 20% ethyl acetate-petroleum ether) to afford 8-fluoro-5- methoxy-2-methylquinoline (25.2 g, 62%) as a yellow solid. MS (ESI, pos. ion) m/z 192[M+H]+. Step 1. 8-chloro-5-methoxy-2-methylquinoline hydrochloride [0204] A 1000-mL 3-necked round-bottom flask was charged with 2-chloro-5-methoxy aniline (50 g, 317 mmol), -butanol (120 mL), concentrated hydrochloric acid (37%, 90 mL), and chloranil (tetrachloro-l ,4-benzoquinone) (78 g, 317 mmol). The resulting solution stirred for 1 h at 100 C in an oil bath. A solution of (E)-crotonaldehyde (28.9 mL, 349 mmol) in -butanol (50 mL) was added dropwise over 1 h. The resulting solution stirred for 1 h at 100 C in an oil bath and was then cooled to 70 C. Tetrahydrofuran (650 mL) was added, and the reaction mixture stirred for 1 h at 70 C and was then cooled to 0 C. The resulting precipitate was held at 0- 5 C for 1 h. The mixture was filtered, the solids were washed with cold (ca. 0 C) THF (2 x 350 mL), and then dried in an oven to afford 8-chloro-5-methoxy-2-methylquinoline hydrochloride (83.0 g, 74%) as a yellow solid. MS (ES, m/z): 208 [M+H]+

According to the analysis of related databases, 62257-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
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