Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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 702-24-9, Safety of 4-Methoxy-N-methylbenzylamine

As shown in Scheme 3, 4-bromo-2,6-di-tert-butylphenyl tert-butyl carbonate5 (115 mg, 0.3 mmol, 1.0 equiv.), 1-(4-methoxyphenyl)-N-methylmethanamine (1.2 equiv.), Pd2(dba)3.CHCl3 (0.1 equiv.), xantphos (0.15 equiv.) and Cs2CO3 (2.5 equiv.) were weighed in a Biotage microwave reaction vial in a glove box. The mixture was treated with toluene (0.05 mM) and the vial was sealed and removed from the glove box. The reaction mixture was heated in an oil bath (100 C., 16 h). The crude mixture was cooled to room temperature and purified by silica gel chromatography using hexane and ethyl acetate as eluents to afford Compound 14 (98 mg, 71% yield).

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, 4-Methoxy-N-methylbenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The University of Kansas; Peterson, Blake R.; Rane, Digamber; (28 pag.)US2019/310263; (2019); A1;,
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Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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. COA of Formula: C9H11BrO

General procedure: 3,5-dimethyl-1-(3-phenoxypropyl)-1H-pyrazole (L1): A solution of 3,5-dimethyl-1H-pyrazole (0.30 g, 3.2 mmol) in DMF/THF (v/v = 1:1, 12 mL) was added to a suspension of NaH (0.15 g, 6.4 mmol) in DMF/THF (v/v = 2:1, 15 mL) and stirred at 60 ¡ãC for 2 h. Then, the resulting solution was added under stirring to a solution of 3-bromopropyl phenyl ether (0.70 g, 3.2 mmol) in DMF (7 mL). The mixture was allowed to stir for 24 h at 60 ¡ãC, cooled, and treated cautiously with H2O (5 mL) to decompose excess NaH. The solvents were then evaporated under reduced pressure. The residue was extracted with ethyl acetate (3 * 15 mL), washed with H2O (2 * 15 mL). The organic phase was dried over MgSO4 and filtered, before the solvent was evaporated under reduced pressure. After workup and purification by chromatographic column on silica gel (hexane/ethyl acetate, 90:10), L1 was obtained as a colorless oil (0.47 g, 64percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 588-63-6, its application will become more common.

Reference:
Article; Ulbrich, Ana H.D.P.S.; Campedelli, Roberta R.; Milani, Jorge L. Sonego; Santos, Joao H.Z. Dos; Casagrande, Osvaldo De L.; Applied Catalysis A: General; vol. 453; (2013); p. 280 – 286;,
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Application of 2674-34-2,Some common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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 dry and nitrogen-flushed 25 ml Schlenk tube equipped with a magnetic stirrer, Mg(3.5 mmol, 3.5 equiv) and dry LiCl (3 mmol, 3.0 equiv) were covered with dry THF(3 mL) and activated by the addition of a few drops of TMSCl. After stirring for 30min, L1 (0.05 mmol, 0.05 equiv) and NiI (0.05 mmol, 0.05 equiv) were added. Thereaction mixture was stirred at 0oC. A solution of aryl bromine (1.0 mmol, 1.0 equiv)and allyl bromide (3.0 mmol, 3.0 equiv) in THF (2 mL) was added in with a syringepump at 0oC (flow rate was 3 mL/h). The resulting mixture was stirred under nitrogenat 0oC for 12 h before the addition of saturated aqueous NH4Cl solution (10 ml). Theresulting mixture was extracted with ethyl acetate (3 ¡Á 30 mL). The organic fractionswere dried over Na2SO4, concentrated in vacuo and purified by silica gelchromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Zhang, Zhan; Xu, Lijun; Chen, Zhengkai; Liu, Zhubo; Miao, Maozhong; Song, Jinyu; Ren, Hongjun; Synlett; vol. 26; 20; (2015); p. 2784 – 2788;,
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Electric Literature of 645-36-3, 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. 645-36-3, name is 2,2-Diethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 26; 5-Chloro-thiophene-2-carboxylic acid (2,2-diethoxyethyl) amide; Add 5-chlorothiophene-2-carboxylic acid (100 g, 0.60 mol) and dichloromethane (1000 mL) to a 3 L three-necked round bottom flask equipped with an overhead stirrer, nitrogen inlet/outlet, addition funnel, and thermocouple. Stir the resulting solution under nitrogen while cooling to 4 0C. Add via addition funnel 2,2-diethyoxyethylamine (88.5 ml, 0.60 mol) in dichloromethane (35 mL) over 12 minutes. Add l-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (123 g, 0.64 mol) to the chilled mixture. Add additional dichloromethane (165 mL) and stir the reaction mixture for 22 h at room temperature. Quench the reaction with water (1000 mL) and separate the resulting layers. Back extract the aqueous layer with dichloromethane (500 mL) and combine the organic layers. Dry over sodium sulfate and purify through a silica gel bed eluting with dichloromethane followed by a mixture of 1% MeOH in dichloromethane and then a mixture of 10% MeOH in dichloromethane to afford 108 g (65%) of the title compound as a white solid. 1H NMR (500 MHz, CDCl3): delta 7.26 (d, J= 3.5 Hz, IH), 6.85 (d, J= 3.5 Hz, IH), 6.37 (bs, IH), 4.57 (t, J= 5.5 Hz, IH), 3.68-3.74 (m, 2H), 3.48-3.57 (m, 4H), 1.19 (t, J= 7.5 Hz, 6H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 645-36-3, name is 2,2-Diethoxyethanamine, 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 645-36-3, Computed Properties of C6H15NO2

49 g of Compound 3 was suspended in a solvent mixture of CH3OH (1 l) and THF (1 l), and 42.4 ml (1.1 eq) of diethyl aminoacetal and 22.8 ml (1.5 eq) of acetic acid were added at room temperature, and the mixture was warmed to 50 C. so that undissolved Compound 3 was completely dissolved, and then the mixture was stirred at room temperature for 1 hour. 18.4 g (1.1 eq) of NaCNBH4 was added at room temperature and the mixture was stirred for 1 hour, followed by performing layer separation using H2O and EA, dehydrating with MgSO4, filtering and drying under reduced pressure, thus obtaining a crude title compound. This crude title compound was purified using column chromatography, yielding 70 g (87.3%) of the title compound (Compound 4). 1H NMR (300 MHz, DMSO-d6, ppm, delta): 9.37 (bs, 1H), 8.28 (s, 1H), 7.69 (d, J=7.58, 1H), 7.49 (bs, 1H), 7.31 (t, J=8.05, 1H), 4.90 (bs, 1H), 4.63 (bs, 2H), 4.15 (s, 3H), 3.60 (m, 4H), 3.15 (bs, 2H), 1.15 (t, J=6.98, 6H)

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

Reference:
Patent; JW PHARMACEUTICAL CORPORATION; Chung, Jae-Uk; Kim, Mi-Jung; Lee, Yong-Sil; Ma, Sang-Ho; Cho, Young-Seok; Lee, Sang-Hak; Na, Young-Jun; Kang, Myoung-Joo; Park, Woul-Seong; US2013/196972; (2013); A1;,
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Application of 1017779-69-9, 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. 1017779-69-9 name is 3-Fluoro-4-(trifluoromethoxy)aniline, 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 120 6-(5,6-difluoro-2-methyl-lH-benzimidazol-l-yl)-N-[3-fluoro-4- ) To a mixture of l-(6-chloropyrazin-2-yl)-5,6-difluoro-2-methyl-lH-benzo[d]imidazole (140 mg, 0.5 mmol) in DME was added K3P04 (360 mg, 0.85 mmol), Pd2dba3 (23 mg, 0.0125 mmol) and X-Phos (24 mg, 0.025 mmol). The reaction mixture was stirred at 100 C for 4 hours, then cooled to room temperature. The product was filtered and washed with DME, then dried under reduced pressure to give the title compound as a white solid (195 mg, 92%). ]H NMR (500 MHz, DMSO-i) delta 10.37 (br. s., 1 H), 8.40 (d, 7=2.52 Hz, 2 H), 7.91 (dd, 7=13.24, 2.52 Hz, 1 H), 7.66 – 7.81 (m, 2 H), 7.52 (t, 7=8.67 Hz, 1 H), 7.44 (dt, 7=8.99, 1.34 Hz, 1 H), 2.58 – 2.70 (S, 3 H); MS m/z 440.4 (ESI) [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-4-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; PTC THERAPEUTICS, INC.; BAIAZITOV, Ramil; CHOI, Soongyu; DU, Wu; HWANG, Seongwoo; LEE, Chang-Sun; LIU, Ronggang; MOON, Young-Choon; PAGET, Steven, D.; REN, Hongyu; SYDORENKO, Nadiya; WILDE, Richard, Gerald; WO2015/76800; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, 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 37895-73-1, Formula: C8H8Br2O2

A dried round-bottom flask was charged with the correspondingdibromoaryl (16.89 mmol, 1 eq) and furan (84.47 mmol, 5 eq) in dry toluene (50 mL) under argonatmosphere. The solution was cooled at -78 C and n-BuLi 1.6M in THF (18.58 mmol, 1.1 eq) was addeddropwise. After complete addition, the solution was warmed up to -40 C, extracted with EtOAc (3x20mL), dried over magnesium sulfate and concentrated under vacuum. The residue was purified bychormatography column (EtOAc/heptane). From 4,5-dibromoveratrol (5 g), 1.91 g of 1,4-dihydro-6,7-dimethoxy-1,4-epoxynaphthalene (56% yield) were obtained as a white solid (“H-NMR (500 MHz,CDCl3): (ppm) 7.01 (s, 21H), 6.94 (s, 21H), 5.65 (s, 21H), 3.82 (s, 6H)). From 5,6-dibromo-1,3-benzodioxole (4.73 g) were obtained 3.17 g of 5,8-dihydro-5,8-epoxynaphtho[2,3-d][1,3]dioxole (81%yield) as a white solid (“H-NMR (300 MHz, CDCl3): (ppm) 7.07 (s, 2H), 6.86 (s, 2H), 5.96 (d, 1H, J =1.4 Hz), 5.91 (d, 1H, J = 1.4 Hz), 5.66 (s, 2H)).

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, 1,2-Dibromo-4,5-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Deyris, Pierre-Alexandre; Caneque-Cobo, Tatiana; Gomes, Filipe; Narbonne, Vanessa; Maestri, Giovanni; Malacria, Max; Heterocycles; vol. 88; 1; (2014); p. 807 – 815;,
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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. 454-90-0, name is 3-(Trifluoromethyl)anisole, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7F3O

1. 2-Methoxy-6-trifluoromethylthiophenol. A three-neck 125 milliliter (mL) flask was purged with N2 and then fitted with a N2 inlet, magnetic stir bar, thermometer and a septum. To the flask was added 3-trifluoromethylanisole (12.8 g, 73 mmol), tetrahydrofuran (THF; 37 mL) and di(i-propyl)-amine (DIPA; 0.2 mL, 1.4 mmol). The solution was cooled to 0 C. and then n-BuLi (28 mL of 2.5 M in hexanes, ca. 70 mmol) was added at a rate to keep the temperature at 10-15 C. The resulting slurry was cooled to 5 C. and allowed to stir for 15 minutes (min). Gas chromatography (GC) analysis (quenched into di-n-propyl disulfide (DPS)(DPS)) indicated an isomer ratio of 77:5. DIPA (0.2 mL) was added and stirring continued for 50 min. GC analysis indicated an isomer ratio of 138:1. A second 125 mL three-neck flask was purged with N2 and fitted with a N2 inlet, Tefloncanula, stir bar and a thermometer. This vessel was loaded with sulfur (2.3 g, 72 mmol) and THF (20 mL). The resulting slurry was cooled to 5 C. and then the aryl lithium slurry was added via canula at a rate to maintain the temperature at 15-20 C. After the addition was complete the resulting amber solution was stirred at 10-15 C. for 35 min. The mixture was poured into 2M HCl (50 mL) and the phases separated. The aqueous phase was extracted with ethyl acetate (EtOAc; 25 mL). The combined organic extracts were washed with brine (75 mL) and dried (MgSO4). The solvents were removed in vacuo leaving an amber oil (16.5 g): gas chromatography/mass spectrometry (GC/MS) analysis indicated the oil contained about 4 percent of the starting anisole and 2 percent of an undesired isomer of the product. 1H NMR (CDCl3): 3.93 (s, 3H), 4.54 (q, J=5 Hz, 1H), 6.99 (d, J=8 Hz, 1H), 7.16 (apparent t, J=8 Hz, 1H), 7.24 (dd, J=8Hz, 2Hz, 1H); MS (GC, 70 eV) 208 (M+, 100%), 187 (95%), 145 (80%).

The synthetic route of 454-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smith, Michael Glenn; Pobanz, Mark Andrew; Roth, Gary A.; Gonzalez, Michael A.; US2002/10375; (2002); 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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

c) 4-(4-Chlorobenzyl)-1-(N-(2-(4-fluorophenoxy)ethyl)amino)piperidine hydrobromide. From a mixture of 1-amino-4-(4-chlorobenzyl)piperidine (500 mg, 2.22 mmol), 2-(4-fluorophenoxy)ethyl bromide (511 mg, 2.33 mmol) and K2CO3 (322 mg, 2.33 mmol) in CH3CN (10 mL) was obtained the title compound as colorless flakes (165 mg, 17%): mp 214-215 C. (dec). 1H NMR (CD3OD) 1.75-2.05 (m, 5H), 2.70 (d, J=6.9, 2H), 3.40-3.52 (m, 2H), 3.83 (d, J=13, 2H), 4.00 (t, J=4.5, 2H), 4.52 (t, J=4.5, 2H), 6.96-7.10 (m, 4H), 7.22 (d, J=8.7, 2H), 7.30 (d, J=8.7, 2H); Anal Calcd for C20H25BrClFN2O: C, 54.13; H, 5.68; N, 6.31. Found: C, 54.23; H, 5.59; N, 6.23.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Co.; Cocensys, Inc.; US6218404; (2001); B1;,
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Electric Literature of 171290-52-1, 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. 171290-52-1 name is 3,5-Dimethoxyphenylacetylene, 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 3: Synthesis of 3,4′,5-trimethoxydiphenylacetylene5 ml of pyrrolidine (99 %) were placed in a 10 ml glass tube fitted with a septum, a magnetic stirring bar and an argon supply. The pyrrolidine was degassed with argon for 30 minutes at room temperature. Afterwards 240 mg of 4-iodoanisol (98 %, 1 .01 mmol, 1 .00 eq.), 12 mg of triphenylphosphine (97 %, 0.044 mmol, 0.044 eq.), 40 mg of palladium on charcoal (10 %, 0.038 mmol, 0.037 eq.) and finally 249.3 mg of 1 -ethynyl-3,5-dimethoxybenzene (98 %, 1 .51 mmol, 1 .50 eq.) were added to the presented pyrrolidine.The mixture was stirred under argon at 85 0C (aluminum block temperature) for 17 hours. The reaction solution was cooled to room temperature and then 10 ml of ethyl acetate were added. Afterwards the suspension was filtrated with a membrane filter (0.45 mum).The solution was treated with 20 ml of a saturated ammonium chloride solution. Then an extraction was performed by extracting twice with 20 ml of ethyl acetate. The organic solutions were dried with sodium sulfate and afterwards concentrated at 40 0C and 180 mbar. The dark yellow crude material was purified by chromatography with ethyl acetate and n-heptane in a ratio of 5:95. The product containing fractions were collected and concentrated at 40 C and 90 mbar. The purified product was analyzed by GC-MS and NMR. The yield was 75 % based on the 4-iodoanisole. GC/MS: Retention time: 21 .61 min, Area %: 99.10 %; M: M+ 268, 253, 225, 210, 195, 182, 167, 152, 139.1H-NMR 300 MHz, d-Chloroform) delta 3.82 ppm (s, 6H, OCH3), 3.85 ppm (s, 3H, OCH3), 6.47 (t, J=2.31 Hz, 1 H, ArH), 6.70 ppm (d, J=2.31 Hz, 2H, ArH), 6.88 – 6.89 ppm (m, 2H, ArH), 7.48 – 7.52 ppm (m, 2H, ArH). 13C-NMR 75 MHz, d- Chloroform) delta 55.30 (OCH3), 56.42 (2xOCH3), 88.10 (C), 89.00 (C), 101 .57 (C), 109.22 (2xCH3), 1 14.02 (2xCH3), 1 15.20 (C), 124.91 (CH), 133.12 (2xCH), 159.71 (C), 160.55 (2xC).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dimethoxyphenylacetylene, and friends who are interested can also refer to it.

Reference:
Patent; DSM IP ASSETS B.V.; LETINOIS, Ulla; BONRATH, Werner; WO2011/9888; (2011); A2;,
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