Month: June 2021

Electric Literature of 36865-41-5, The chemical industry reduces the impact on the environment during synthesis 36865-41-5, name is 1-Bromo-3-methoxypropane, I believe this compound will play a more active role in future production and life.

To a solution of Intermediate 7 (4.02 g, 20.7 minol) in DMF (50 mL) sodium hydride 60% in mineral oil (992 mg, 22.7 minol) was added carefully at 0 00. The ice bath was removed and the mixture was stirred for 30 min at room temperature. The resulting suspension was cooled at 00 and 1-bromo-3-methoxypropane (2.3 mL, 20.7 minol) was added. The reaction mixture wasstirred over night at room temperature. The mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washes with brine, dried over Na2SO4 and evaporated. The crude material was purified by flash-chromatography on silica gel to yield the desired product (4.6 g, 85%).1H-NMR (400MHz, DMSO-d6): oe [ppm]= 1.02 (d, 3H), 1.80 (quin, 2H), 2.24 (dd, IH), 2.62 (dd, IH), 3.21 (s, 3H), 3.24-3.36 (m, 3H), 3.57-3.68 (m, IH), 3.82-3.93 (m, IH), 5.55 (s, 2H), 6.53- 6.61 (m, 2H), 7.42 – 7.56 (m, 2H).UPLO (Method 2): R = 0.79; MS (ESIpos): mz [M÷H] 276.

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, 1-Bromo-3-methoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; QUANZ-SCHOEFFEL, Maria; MUeLLER, Thomas; GUeNTHER, Judith; BOeHNKE, Niels; GRIEBENOW, Nils; BARAK, Naomi; BOeMER, Ulf; NEUHAUS, Roland; OSMERS, Maren; KOPITZ, Charlotte Christine; KAULFUSS, Stefan; REHWINKEL, Hartmut; WEISKE, Joerg; BADER, Benjamin; CHRISTIAN, Sven; HILLIG, Roman; (426 pag.)WO2018/86703; (2018); A1;,
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Reference of 22236-10-8, These common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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.

2-Butyl-4-{[4-(difluoromethoxy)phenyl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide; 2-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.63g, 2.1mmol) and 4-(difluoromethoxy)-aniline (0.67g, 4.2mmol) were mixed in MeCN (4mL, dry). The mixture was put in a microwave reactor at 1600C for 1 hour, then for additional 1 hour then for 1 hour more. It was evaporated to dryness. The residue was purified by column chromatography (ISOLUTE SI, 50g/150mL), eluting with dichloromethane/heptane (50:50, then 75:25), to give the title compound (0.688g, 78%) as a yellow solid;

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/73364; (2006); A1;,
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These common heterocyclic compound, 2398-37-0, name is 1-Bromo-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. Computed Properties of C7H7BrO

The advantageous effect of adding zinc chloride to an amination reaction was demonstrated in the amination reaction of 3-bromoanisole. the results of which are summarized in Table 10. When 3-bromoanisole was reacted under the standard lithium amide amination conditions, using lithium amide (10 eq.) in the presence of (CyPF-^-Bu)PdCl2 (1 mol%) in DME gave a complicated mixture of products was obtained (Table 10, Entry 1). When conducted in the presence of zinc chloride and TMEDA, however, the reaction could successfully gave the desired monoarylation product, 3-methoxyaniline, although at high concentrationsN,N-dimethyl-3-methoxyaniline was formed in a significant amount as a by- product (Table 10, Entries 3 and 4). Under optimized conditions (Table 10, Entries 8 and 9), 3-methoxyaniline was formed selectively in good yield.

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

Reference:
Patent; YALE UNIVERSITY; WO2007/109365; (2007); A2;,
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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, HPLC of Formula: C7H8BrNO

To a stirred 100 mL RBF was added 5-bromo-2-methoxyaniline (7 g, 34.6 mmol) and DIEA (12.05 mL, 69.3 mmol) in DCM (100 mL). At 0 C, furan-2-carbonyl chloride (3.41 mL, 34.6 mmol) was added dropwise. The reaction mixture was stirred at 0 C and allowed to warm to RT overnight. The reaction mixture was diluted with water and extracted with DCM. The combined organic layers were washed with brine and dried over MgSO4. The solution was filtered and concentrated in vacuo. The sample was preloaded on silica and purified with flash chromatography on a CombiFlash silica gel column (80 g, Teledyne Isco, gradient 20% EtOAc in hexanes) to give Example 209.1. LCMS (ESI) m/z= 297 [M+Hf?.

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

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
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Some common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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. Computed Properties of C7H8FNO

Compound a1-2 (8.0 g, 43 mmol) was placed in a 500 mL single-necked reaction flask and concentrated sulfuricacid (100 mL) was added under stirring at a constant rate to dissolve the substrate. Concentrated nitric acid (6.15 mL,48 mmol) was slowly added dropwise to the stirred reaction flask at -20 C and stirred at that temperature for 5 minutes.The progress of the reaction was checked by TLC. After the reaction of the substrate was complete, the reaction mixturewas poured into iced water. In -20 C ice bath, the aqueous solution of hydroxide/water (150 mL/300 mL) was slowly added to the reaction system and pH was adjusted to 8-9. After neutralization, the reaction solution was extracted threetimes with ethyl acetate/water system. The organic layer was separated, washed with water and then saturated brine,dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the compound 4-fluoro-2-methoxy-5-nitroaniline a1 (8.7 g) which was directly used in the next step. Yield: 80%; purity: 100%; MS m/z(ESI): 187.0 [M+H]+;1HNMR (400 MHz, DMSO-d6): delta 7.34 (d, J = 7.8 Hz, 1H), 7.04 (d, J = 13.4 Hz, 1H), 5.25 (brs, 2H), 3.90 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 450-91-9, its application will become more common.

Reference:
Patent; Shanghai Haiyan Pharmaceutical Technology Co., Ltd.; Yangtze River Pharmaceutical Group Co., Ltd.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; LEI, Jing; WEN, Chong; ZHANG, Zhiyuan; HE, Xiangyu; (57 pag.)EP3173412; (2017); A1;,
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Related Products of 24332-20-5, 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. 24332-20-5 name is 1,1,2-Trimethoxyethane, 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.

To a solution of methoxyacetaldehyde dimethylacetal (5 g, 41.63 mmol) in methanol (20 ml) was added a solution of hydroxylamine hydrochloride (2.9 g, 41.73 mmol) in water (10 ml). The reaction was stirred at room temperature for 18 hours. To the reaction was then added an aqueous solution of sodium hydroxide (1.67 g, 41.6 mmol in 10 ml water) and stirred for 3 hours at room temperature. The methanol was removed in vacuo and the mixture acidified with concentrated hydrochloric acid to pH 5-6, before extracting with f-butylmethyl ether, drying over Na2SO4 and concentrating in vacuo to afford the title compound as a 1.5:1 mixture of E/Z isomers (2.64 g, 71% yield).1HNMR (CDCI3): 3.4 (m, 3H), 4.05 (d, 1.2H), 4.3 (d, 0.8H), 6.9 (t, 0.4H), 7.5 (t, 0.6H), 8.55 (br s, 0.6H), 8.85 (br s, 0.4H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1,2-Trimethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
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Electric Literature of 16452-01-0, 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. 16452-01-0, name is 3-Methoxy-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 6-Methyl-7-methoxy-quinolineglycerol(2.5 eq) FeSO4«7H2O( 0.03 eq)[0182] Using a minimal amount of dioxane, 3-methoxy-4-methylaniline (5.00 g, 36.5 mmol) was slowly added to a mixture of sodium m-nitrobenzenesulfonate (6.62 g, 29.4 mmol), MsOH (20 mL), and FeSO4*7H2O (0.39 g, 1.4 mmol) in a 10OmL round bottom flask heated to an internal temperature of 145-155 0C. Glycerol( 10.75 g, 116.8 mmol) was then added dropwise via addition funnel while keeping the internal temperature at 145-155C. After addition, the reaction was stirred in a 150 0C oil bath until LCMS indicated completion (4-6 h). After being cooled to rt, ice (2Og) was added, then the solution was neutralized with IO N NaOH (calculated to same eq of MsOH) at a speed to keep the internal temperature below 40 0C. A thick suspension appeared after addition, and this was extracted with EtOAc (50 mL x 3). The organic layer was filtered through a Celite pad to remove insoluble black particles and then purified by flash column chromatography on silica gel to give the desired product (5.0 g, 79%). MS (ES) mlz 174.1 (M+ H+).

The chemical industry reduces the impact on the environment during synthesis 3-Methoxy-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; FAN, Pinchen; GLEASON, Mark, M.; JAEN, Juan, C.; LI, Lianfa; MCMAHON, Jeffrey, P.; POWERS, Jay; ZENG, Yibin; ZHANG, Penglie; WO2010/54006; (2010); A1;,
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Synthetic Route of 36942-56-0, 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. 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2.5M nBuLi (1.8 mL, 4.5 mmol) was added dropwise over 5 minutes into a mixture of 2-bromo-4-methoxy-1-methylbenzene (750 mg, 3.73 mmol) in anhydrous THF (30 mL) at -78 C. After the mixture was stirred at -78 C. for 20 minutes, anhydrous trimethyl borate (0.62 g, 6 mmol) was added into the solution at -78 C. The reaction mixture was brought to room temperature for over period of 2 h. The reaction was quenched by 2N HCl (1 mL). The THF was removed by vacuum. The crude product was diluted with 2N HCl (100 mL). The acidic solution was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate fraction was dried over sodium sulfate. The sodium sulfate was removed by filtration and the solvent was removed by vacuum to yield a pale yellow solid (0.43 g, 69%).

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, 2-Bromo-4-methoxy-1-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TargeGen, Inc.; US2005/245524; (2005); 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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-4-fluoro-2-methoxybenzene

A solution of dry diisopropylamine (10 g, 99 mmol) in dry THFunder nitrogen was cooled with a -78 C bath, n-butyl lithium (2.50 M in hexane, 40 mL, 99 mmol) was added andthe solution was stirred at -78 C for 20 minutes. 1-Bromo-4-fluoro-2-methoxybenzene (17.0 g, 82.5 mmol) wasadded. After stirring at -78 C for 2 hours, the solution was bubbled with CO2 and then warmed to 0 C. Then 1 NHCl was added until pH=3-4 and the mixtue was extracted with AcOEt. The combined organic layers were washedwith brine, dried over anhydrous sodium sulphate and concentrated to afford 3-bromo-6-fluoro-2-methoxybenzoicacid.

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

Reference:
Patent; Merck Sharp & Dohme Corp.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; (128 pag.)EP2744499; (2016); B1;,
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Application of 1663-61-2, 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. 1663-61-2, name is (Triethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Method B (microwave irradiation) – The reaction mixture composed of cinnamic acid hydrazide 2 (0.50 g, 3.0 mmol), triethyl orthoester (6.0 mmol) and 2 mL of glacial AcOH was placed into 10 mL crimp-sealed thick-walled glass tube. The reaction vessel was placed in CEM Discover microwave-enhanced synthesis system operating at 125 +/- 5 C, power 250 W and kept for 10 min. After cooling, the excessive orthoester and AcOH were evaporated under reduced pressure. The crude product was purified by column chromatography with silica gel and an eluent of benzene/AcOEt, 1:5, v/v.

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, (Triethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Tetrahedron Letters; vol. 53; 1; (2012); p. 76 – 77;,
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