Month: February 2021

Electric Literature of 102503-23-1, 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. 102503-23-1, name is 1-(2,4-Dimethoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: N-(2,4-dimethoxybenzyl)-N-methyl-3-phenylprop-2-yn-1-amine (5a). CuI (20 mg, 0.10 mmol) was added to a solution of phenylacetylene(510.6 mg, 5.0 mmol), HCHO (36% aq., 2 mL),N-methyl(2,4-dimethoxybenzyl)amine (1.09 g, 6.0 mmol) in DMSO (10.0mL). The resulting yellow green solution was stirred at room temperatureovernight and then diluted with H2O (10 mL), extracted with Et2O (15 mL x 3). The combined extractswas washed with H2O (2 x), brine (2 x) respectively, dried over Na2SO4, filtered, concentrated. Theresultant yellow oil was purified through flash column chromatography (silica gel, EtOAc/Hex = 1:6 to1:3) to give the product (5a, 1.14 g, 96%).

The synthetic route of 1-(2,4-Dimethoxyphenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Miao; Odelberg, Shannon J.; Tong, Zongzhong; Li, Dean Y.; Looper, Ryan E.; Tetrahedron; vol. 69; 27-28; (2013); p. 5744 – 5750;,
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Synthetic Route of 37895-73-1,Some common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-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: To a Schlenk tube (20 mL) were added PdCl2(MeCN)2 (26 mg, 0.10 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 0.16 g, 0.40 mmol). The Schlenk tube was capped with a rubber septum and then evacuated and purged with argon. The evacuation-purge operation was repeated twice. To the tube was added 1,4-dioxane (6.0 mL), 1,2-dibromobenzene (1.63 g, 0.82 mL, 5.0 mmol), NEt3 (3.04 g, 4.18 mL, 30.0 mmol), and pinacolborane (2.18 mL, 1.92 g, 15.0 mmol) in this order with syringes, respectively, through the septum. The reaction mixture was heated at 110 C and the progress of the reaction was monitored by gas chromatography. After the complete consumption of the dibromide was confirmed, the reaction mixture was then allowed to cool to room temperature. The resulting solution was filtered through a thin pad of Celite with EtOAc as the eluent. The organic solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography on silica gel followed by recrystallization from hexane at -20 C, giving rise to 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (3h, 0.83 g, 51%) as a colorless solid.

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-Dibromo-4,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Shimizu, Masaki; Nagao, Ikuhiro; Tomioka, Yosuke; Kadowaki, Tsugumi; Hiyama, Tamejiro; Tetrahedron; vol. 67; 41; (2011); p. 8014 – 8026;,
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Synthetic Route of 123652-95-9, The chemical industry reduces the impact on the environment during synthesis 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine, I believe this compound will play a more active role in future production and life.

To a screw-capped vial equipped with a magnetic stir bar were added 3,4- dimethylthieno[2,3-c]pyridazine-6-carboxylic acid (Intermediate 2) (35 mg, 0.17 mmol), DMF (1 mL), DIEA (90 tL, 0.48 mmol), and HATU (77 mg, 0.20 mmol). This mixture was allowed to stir at ambient temperature for 30 minutes, and then excess (3-fluoro-4- methoxyphenyl)methanamine (2.1) was added. After stirring at room temperature for 30 minutes, purification by reversed-phase HPLC (eluting with water/0. 1% trifluoroacetic acid and acetonitrile) afforded the title compound. LCMS: RT = 0.81 mm, >99% 254 nm,>99% 215 nm; mlz (M + 1)= 346. ?H NMR (400 MHz, d6-DMSO) oe 9.5 (t, J= 5.8 Hz, 1H), 8.3 (s, 1H), 7.1-7.3 (m, 3H), 4.5 (d, J= 5.8 Hz, 2H), 3.8 (s, 3H), 2.7 (s, 3H), 2.6 (s, 3H); HRMS calculated for C,7H,6FN302S (M+H) mlz: 346.1026, measured: 346.1023.

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, (3-Fluoro-4-methoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig, W.; CONN, P., Jeffrey; WOOD, Michael, R.; POSLUSNEY, Michael, S.; TARR, James, C.; MELANCON, Bruce, J.; WO2015/27214; (2015); 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. 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 31576-51-9

In a round bottom flask under nitrogen 150 mg (0.35 mmol) of intermediate Awas dissolved in 5 mL ofCH2Ch and 0.18g of DIPEA (1.4 mmol) was added followed by 125 mg (1.05 mmol) of2-(2-Methoxy-ethoxy)-ethylamine. The mixture was allowed to stirovernight and then condensed in vacuo. The residue was dissolved in 20 mL of EtOAc andwashed with 2x 20 mL of water, 20 mL of brine, dried over Na2S04 and condensed in vacuo.Purification by biotage flash chromatography (Si02, MeOH/CH2Ch/Et3N gradient) affords 99mg of the title compound as a clear oil

The synthetic route of 31576-51-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZAFGEN, INC.; ZAHLER, Robert; VATH, James, F.; WO2013/169860; (2013); A1;,
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Related Products of 1515-89-5, A common heterocyclic compound, 1515-89-5, name is 1-Bromo-3-(methoxymethyl)benzene, molecular formula is C8H9BrO, 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 1-bromo-3-methoxymethyl-benzene. (286 mg, 1.42 MMOL) and bis- (PINACOLATE) DIBORON. (397 mg, 1.56 MMOL) in DMSO (8 mL) are added KOAC (419 mg, 4.27 MMOL) and Pd (DPPF) CI2. CH2CI2 (58 mg, 0.071 MMOL). The reaction mixture is stirred at 80 C under nitrogen atomosphere for 1 h. After dilution with ether, the mixture is washed with water (x2) and brine. The organic layer is dried over MGS04, filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography (n-hexane: EtOAc=10: 1) to give the corresponding boron ester.

The synthetic route of 1515-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/69256; (2004); A1;,
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Related Products of 22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 9; 2-ButyI-4-{[4-(difluoromethoxy)phenyl]amino}-5-phenyIisothiazol-3(2H)-one 1,1-dioxide; 2-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.63g, 2.1 mmol) and 4- (difluoromethoxy)-aniline (0.67g, 4.2mmol) were mixed in MeCN (4 mL, dry). The mixture EPO was put in the microwave reactor at 160 0C for 1 h, then additional 1 h and then 1 h more. It was evaporated to dryness. The residue was purified by column chromatography (ISOLUTE SI, 50 g/150 mL), eluting with DCM/heptane (50:50, then 75:25), to give the title compound (0.688g, 78%) as a yellow solid;

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-(Difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2006/73363; (2006); A1;,
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Synthetic Route of 53087-13-1, 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.2 g, 0.76 mmol), 3- cyanophenylboronic acid (0.223 g, 1.52 mmol), barium hydroxide (0.285 g, 1.67 mmol), Pd(PPh3)4 (0.088 g, 0.076 mmol), DME (5 mL) and H2O (3 niL) was heated (80C) for 6 hours with vigorous stirring under an argon atmosphere. The reaction mixture was cooled to RT, diluted with ethyl acetate, and filtered through a plug of celite. The filtrate was diluted with brine; the organic phase was separated, dried (MgSO4), and concentrated in vacuo. The residue obtained was purified by flash column chromatography (20% diethyl ether-hexane) to give 75 (0.130 g, 60% yield) as a viscous liquid.[0411] 75 was confirmed as follows: 1H NMR (500 MHz, CDCl3) delta 7.85 (t, J = 2.5 Hz, 1H), 7.78 (dt, J = 7.5 Hz, J = 1.5 Hz, 1H), 7.63 (dt, J = 8.0 Hz, J = 1.5 Hz, 1H), 7.53 (t, J = 8.0 Hz, 1H), 7.46 (d, J = 7.5 Hz, 2H), 7.44-7.37 (m, 3H), 7.35 (t, J = 7.0 Hz, 1H), 7.18-7.14 (m, 2H), 7.02 (dd, J = 8.5 Hz, J = 2.5 Hz, 1H), 5.17 (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-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NORTHEASTERN UNIVERSITY; WO2009/52319; (2009); A1;,
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Reference of 7252-83-7, 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 100-mL, three-neck flask was charged with 2-bromo-l,l-dimethoxyethane 4 (23.2 g (16 mL, 137.2 mmol) and aqueous HBr (47.6% HBr by wt, 8.8 mmol/mL, 6.6 mL, 58.8 mmol), and the reaction mixture was heated to reflux (55C) for 2 hours. The mixture was allowed to cool to 40C, and solid NaHCC3 was added in small portions, until evolution of gas ceased. The resulting suspension was filtered, under vacuum, into a 500-mL, three-neck flask, and the filter cake was washed with isopropanol (200 mL). Solid 3,5-dibromopyrazin-2-amine (3) (12.0 g, 47.2 mmol) was added into the isopropanol filtrate, and the reaction mixture was heated at reflux (78C) for 16 hours. The resulting suspension was cooled to room temperature, filtered, the cake was washed with cold isopropanol (100 mL), and then the cake was dried under vacuum. The cake was transferred into a three-neck flask, into which, water (200 mL) was added, followed by solid K2CC3, in small portions, until gas evolution ceased, after which the reaction was stirred for 30 minutes. The resulting precipitate was isolated by filtration, and washed with water (200 mL). The solid was dried at 50C, to constant weight, then dissolved in THF, filtered through a plug (celite, silica gel, and charcoal). The solvent was removed under vacuum, to give 12.0 g of the desired product (5) as a white solid at 99% purity, as determined by NMR and LC-MS. IH NMR (500 MHz, CDC13) delta 8.26 (s, IH), 7.84 (d, J = 1.0 Hz, IH), 7.78 (d, J = 1.1 Hz, IH); 13C NMR (126 MHz, CDC13) delta 136.93, 134.06, 120.29, 119.26, 115.78.

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-1,1-dimethoxyethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; ONDARI, Mark E.; WELSH, Dean M.; FROESE, Robert DJ; NA, Hong-Yeop; (38 pag.)WO2016/209895; (2016); A1;,
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Related Products of 102503-23-1, 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 102503-23-1 as follows.

Reference Example 60; 1- (2, 4-dimethoxyphenyl) -N- { [4-fluoro-5- (2-fluoropyridin-3-yl) – lH-pyrrol-3-yl]methyl }-N-methylmethanamine; Sodium hydride (60% in oil, 2.23 g) was washed twice with hexane and suspended in tetrahydrofuran (180 mL) . To the suspension was added dropwise a solution of l-(2,4- dimethoxyphenyl) -N-methylmethanamine (9.09 g) in tetrahydrofuran (10 mL) at 0C. After the completion of the dropwise addition, the mixture was stirred at 600C for 18 hr. The reaction mixture was cooled to 0C, a solution of 3- (4, 4- difluoro-3-methylene-3, 4-dihydro-2H-pyrrol-5-yl) -2- fluoropyridine (9.64 g) in tetrahydrofuran (10 mL) was added dropwise, and the mixture was stirred at the same temperature for 1 hr. Ice water and saturated brine were added, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate) to give the title compound as a yellow oil (yield 16.8 g, 97%) . 1H-NMR (CDCl3) delta: 2.24(3H,s), 3.51(2H,s), 3.54(2H,s), 3.79(3H,s), 3.80(3H,s), 6.45(lH,s), 6.42-6.50 (IH,m) , 6.68(lH,dd, J=4.7,3.6Hz) , 7.18-7.29 (2H,m) ,7.98 ( IH, ddd, J=4.5, 1.9, 1.5Hz) , 8.25 (IH, ddd, J=IO .2 , 8.0, 1.9Hz) , 8.67(1HzS) .

According to the analysis of related databases, 102503-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/108380; (2008); A2;,
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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. 136-90-3, name is 4-Methoxy-3-methylphenylamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H11NO

General procedure: 4-amino-6-chloropyrimidine (200 mg, 1.54 mmol) and KI(127.82 mg, 0.77 mmol) was dissolved in ethanol (35 mL). Trifluoroaceticacid (200 mL) was added after stirring and heating10 min for activating pyrimidine. Then to a stirred solution ofsubstituted aniline (1.23 mmol) in ethanol (15 mL) was added byway of drip for 1 h. The resulting mixture was heated to reflux for36 h, allowed to cool to room temperature, and concentrated invacuo. Then the solid residue was diluted with ethyl acetate and asaturated aqueous solution of NaHCO3. The aqueous layer wasseparated and extracted with ethyl acetate. The organic phase waswashed with brine, dried (Na2SO4), filtered, and concentrated. Purificationof the crude product by silica gel column chromatography(ethyl acetate/light petroleum, 2:1 and 1:1), provided the desiredproduct (batch1). Substituted aniline (2,6-dichloro and 3,5-dimethoxy) (200 mg) was dissolved in CH2Cl2 (15 mL) was addedby way of drip phosgene which dissolved in CH2Cl2 (20 mL)(batch1/phosgene, 2:1 (mol)) at 0 C for 0.5 h. The resulting mixturewas heated to reflux for 3e6 h, allowed to cool to room temperature,and concentrated in vacuo. Then the solid residue was dilutedwith ethyl acetate and a saturated aqueous solution of NaHCO3. Theaqueous layer was separated and extracted with ethyl acetate. Theorganic phase was washed with brine, dried (Na2SO4), filtered, andconcentrated. Purification of the crude product by silica gel columnchromatography (CH2Cl2/MeOH/aqueous NH3, 96:3:1), providedthe desired product (batch2). Batch1 and batch2 (batch1/batch2,5:6 (mol)) were dissolved in toluene (10 mL,18.89 mmol), theresulting mixture was heated to reflux for 8e10 h, allowed to coolto room temperature, then filtered by toluene to provide the endproduct(the residue).

According to the analysis of related databases, 136-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xie, Zixin; Wu, Kaiqi; Wang, Yuexuan; Pan, Yaqian; Chen, Bo; Cheng, Donghua; Pan, Suwei; Guo, Taoning; Du, Xuze; Fang, Longcheng; Wang, Xuebao; Ye, Faqing; European Journal of Medicinal Chemistry; vol. 187; (2020);,
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