Month: February 2021

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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25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: ethers-buliding-blocks

25 mL single neck flask was charged with 2-bromo-1,4-dimethoxybenzene (1.0 g, 4.6 mmol), AcOH (5 mL),Then slowly add HNO3 (0.4 mL) dropwise,A large number of yellow solid solution was precipitated,After 0.5h,filter,Rinse the residue with plenty of water,Finally dried in a vacuum oven,Obtained bright yellow solid powder compound 4 (1.1 g, 92%).

The synthetic route of 25245-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Zhao Xin; Yin Zhijian; Zhan Tianguang; (17 pag.)CN107353242; (2017); A;,
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Synthetic Route of 22483-09-6, 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 22483-09-6 as follows.

(3,4,5-Trimethoxybenzylidene)-(2,2-dimethoxyethyl)amine (11c). Aminoacetaldehyde dimethylacetal (20.0 mL, 19.5 g, 0.185 mol) was dissolved in chloroform (80 mL) and MgSO4 (15 g) was added. Then 3,4,5-trimethoxybenzaldehyde (10c, 10.03 g, 0.05112 mol) was also added and the mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with chloroform (70 mL), washed with water (4*150 mL), brine (150 mL), dried (Na2SO4), and concentrated to provide the pure imine as a colorless oil (14.47 g, 100%). 1H NMR (300 MHz CDCl3) 8.10 (s, 1H), 6.91 (s, 2H), 4.58 (t, J=5.4 Hz, 1H), 3.81 (s, 6H), 3.79 (s, 3H), 3.69 (s, J, =5.4 Hz, J2=1.2 Hz, 2H), 3.33 (s, 6H).

According to the analysis of related databases, 22483-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cushman, Mark S.; Ioanoviciu, Alexandra S.; Pommier, Yves G.; US2008/242692; (2008); A1;,
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Synthetic Route of 2734-70-5, These common heterocyclic compound, 2734-70-5, name is 2,6-Dimethoxyaniline, 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: To a 0.5 M solution of the acid 9/10 in dichloromethane under nitrogen atmosphere, was added oxalyl chloride (2 eq.) and a few drops of DMF at room temperature. After effervescence subsided, the mixture was heated to reflux at 45 ¡ãC for 2 h. It was then cooled to room temperature, concentrated in vacuo, co-evaporated three times with toluene and then re-dissolved in dichloromethane. The aniline (2 eq.) was then added at 0 ¡ãC, followed by DIPEA (3 eq.) and the mixture stirred overnight at room temperature. The reaction was quenched by addition of NaHCO3 and the aqueous layer was extracted three times with dichloromethane. The combined organic layer was washed once with brine, dried over Na2SO4 and concentrated in vacuo. Purification by silica gel chromatography using a toluene/acetone or dichloromethane/methanol solvent system gave access to the pure protected amides (30percent?75percent yields).

The synthetic route of 2734-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chofor, Rene; Risseeuw, Martijn D.P.; Pouyez, Jenny; Johny, Chinchu; Wouters, Johan; Dowd, Cynthia S.; Couch, Robin D.; Van Calenbergh, Serge; Molecules; vol. 19; 2; (2014); p. 2571 – 2587;,
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These common heterocyclic compound, 202865-59-6, name is 2-Bromo-4,6-difluoroanisole, 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. Safety of 2-Bromo-4,6-difluoroanisole

Palladium (II) acetate (0.040 g, 0.18 mmol) and xantphos (0.104 g, 0.179 mmol) were stirred in toluene (1 mL) at room temperature for 2 min. 1- Bromo-3,5-difluoro-2-methoxybenzene (4.00 g, 17.9 mmol), (diphenylmethylene)hydrazine (3.52 g, 17.9 mmol) and sodium tert-butoxide (2.41 g, 25.1 mmol) were added followed by the addition of toluene (4 mL). The mixture was degassed twice and was stirred for 6 h at 100 C under argon. After cooling, EtOAc and H20 were added. The organic layer was separated. The aqueous phase was extracted one more time with EtOAc. The combined EtOAc layers were washed with I0, then brine, dried over MgSO^ filtered, and concentrated. The crude was dissolved in a small amount of CH2CI2 and added to a silica gel column and was eluted with hexanes/EtOAc to give Intermediate 12A (6.0 g, 15 mmol, 84% yield). lH NMR (400 MHz, CDC13) delta ppm 3.63 (br. s, 3 H), 6.14 – 6.38 (m, 1 H), 7.08 – 7.20 (m, 5 H), 7.45 – 7.68 (m, 5 H), 7.97 (s, 1 H). 9F NMR (376.5 MHz, Acetone-d6) delta ppm -115.46, -129.88.

The synthetic route of 2-Bromo-4,6-difluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; THIBEAULT, Carl; CLARK, Charles, G.; DELUCCA, Indawati; HU, Carol, Hui; JEON, Yoon; LAM, Patrick, Y., S.; QIAO, Jennifer, X.; YANG, Wu; WANG, Yufeng; WANG, Tammy, C.; WO2014/22349; (2014); A1;,
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