Month: February 2021

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 450-88-4 as follows. Quality Control of 1-Bromo-4-fluoro-2-methoxybenzene

General procedure: Example 3Tandem Borylation/Dehalogenation of 1-Chloro-4-fluoro-3-Substituted- and 1-Bromo-4-fluoro-3-Substituted BenzenesTandem borylation/dehalogenation was also investigated as a strategy for the ortho-borylation of arenes that are substituted with an electron-withdrawing group. The scheme below illustrates the tandem borylation/dehalogenation methodology which was investigated. As discussed above, in the case of arenes that are substituted with an electron-withdrawing group, iridium-catalyzed C-H activation-borylation of the arene is typically governed by steric effects. In tandem borylation/dehalogenation, the substrate can include an electron-withdrawing group and a sacrificial atom (e.g., a halogen such as Cl or Br) positioned para to the electron-withdrawing group, so as to sterically hinder attack of the iridium catalyst at the otherwise sterically favored position meta to the electron-withdrawing group. As a result, iridium-catalyzed C-H activation-borylation of the arene exclusively generates the ortho-borylated (electronic) product. Subsequent dehalogenation can afford exclusively the desired electronic product.[0337] General Procedure for Borylation [0338] In a nitrogen atmosphere glovebox B2Pin2 (140 mg, 0.55 mmol) was weighed into a 20 mL vial containing a magnetic stir bar. [Ir(OMe)cod]2 (6.6 mg, 0.02 mmol) and 4,4?-di-tert-butyl-2,2?-dipyridyl ligand (5.4 mg, 0.02 mmol) were weighed into two separate test tubes, each being diluted with THF (2 mL). The [Ir(OMe)cod]2 solution was transferred into the 20 mL vial containing B2Pin2. This mixture was stirred until a golden yellow clear solution was obtained. The solution containing ligand was transferred into the vial, and the mixture was stirred until it became a dark brown color solution. The substrate (1 mmol) was added to the vial, which was then sealed. The reaction mixture stirred for 24 h at rt, after which the vial was removed from the glovebox. The reaction mixture was passed through a short plug of silica eluting with a 10:1 hexane/EtOAc solution (2¡Á10 mL). The volatiles were removed by rotary evaporation affording the product, which was characterized using standard methodologies. 1-Bromo-4-fluoro-2-methoxybenzene was borylated using the general procedure described above. After workup, a white solid was obtained (0.313 g, 95%): mp 104-105 C.; 1H NMR (500 MHz, CDCl3) delta 7.89 (d, J=6.5 Hz, 1H), 6.61 (d, J=11.0 Hz, 1H), 3.72 (s, 3H), 1.35 (s, 12H); 13C NMR (125 MHz, CDCl3) delta 167.6 (d, J=251.2 Hz), 159.5 (d, J=11.4 Hz), 140.2 (d, J=10.4 Hz), 108.3 (d, J=22.7 Hz), 105.9 (d, J=2.9 Hz), 83.9, 56.4, 24.8; 19F NMR (470 MHz, CDCl3) delta 100.4; 1113 NMR (160 MHz, CDCl3) delta 29.5 (br s).

According to the analysis of related databases, 450-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smith, III, Milton R.; Maleczka, JR., Robert E.; Li, Hao; Jayasundara, Chathurika; Oppenheimer, Jossian; Sabasovs, Dmitrijs; US2015/65743; (2015); 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. 41864-45-3, name is 4,5-Dimethoxy-2-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 41864-45-3

The compound 68 (150 mg, 0.415 mmol) was dissolved in acetic acid (0.75 mL). 4,5-dimethoxy-2-methylaniline (84 mg, 0.501 mmol) was added to the solution. The mixture was stirred at 100C for 3 hours. Water was added to the reaction mixture. The mixture was extracted with ethyl acetate. The organic layer was washed by brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica-gel column chromatography (ethyl acetate-n-hexane) to give the compound 1-1252 (112 mg, yield 56%). 1H-NMR (DMSO-D6) delta: 1.24 (t, J = 7.2 Hz, 3H), 1.98 (s, 3H), 3.69 (s, 3H), 3.74 (s, 3H), 4.26 (q, J = 6.8, 14.0 Hz, 2H), 5.37 (s, 2H), 6.76 (s, 1H), 6.83 (s, 1H), 7.36 (dd, J = 6.8 Hz, 2H), 9.05 (s, 1H).

The synthetic route of 41864-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd; TANAKA, Satoru; OGAWA, Tomoyuki; KAI, Hiroyuki; OGATA, Yuki; HIRAI, Keiichiro; KUROSE, Noriyuki; FUJII, Yasuhiko; (438 pag.)EP3287443; (2018); A1;,
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Some common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, molecular formula is C9H13NO, 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: C9H13NO

Respectively, weighed o-iodobenzoic acid 252 mg,N-methyl-4-methoxybenzylamine 68 mg was added to 10 ml of chloroform,The reaction was stirred under reflux for 6 hours.Natural cooling to room temperature after pumping to remove IBX And its reduction products o-iodo benzoic acid(IBA),The filtrate was washed with 10percent Na0H solution,1M hydrochloric acid, water and saturated sodium chloride solution were washed 3 times,Each about 10 ml,The solvent chloroform was removed by rotary evaporation,The product was directly characterized by NMR, and the yield of 4-methoxybenzaldehyde was 91percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 702-24-9, its application will become more common.

Reference:
Patent; Guizhou University; CONG, Hang; WANG, Fang; TAO, Zhu; (8 pag.)CN105732351; (2016); A;,
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Synthetic Route of 645-36-3, A common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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.

2,2-Diethoxyethylamine (505 muL, 3.48 mmol) and Et3N (485 muL,3.48 mmol) were added to a soln of pyrimidine 3 (0.5 g, 2.32 mmol)in MeOH (25 mL), and the mixture was stirred at r.t. for 20 h. H2O(100 mL) was added and the precipitate was collected by filtration,dried, and crystallized (hexane) to give a colorless solid; yield: 0.62g (82%); mp 84-85 C.IR (KBr): 3320 (NH), 2220 (CN) cm-1.1H NMR (300 MHz, CDCl3): delta = 1.26 (t, J = 6.9 Hz, 6 H, 2 ¡Á CH3),2.53 (s, 3 H, SCH3), 3.58 (dq, 2J = 9.6 Hz, 3J = 6.9 Hz, 2 H,2 ¡Á CHAHBCH3), 3.69 (t, J = 5.4 Hz, 2 H, NCH2), 3.76 (dq, 2J = 9.6Hz, 3J = 6.9 Hz, 2 H, 2 ¡Á CHAHBCH3), 4.02 (s, 3 H, OCH3), 4.61 (t,J = 5.4 Hz, 1 H, OCH), 5.65 (t, J = 5.4 Hz, 1 H, NH).13C NMR (75 MHz, CDCl3): delta = 14.5, 15.6, 43.8, 54.9, 63.3, 70.6,100.7, 114.7, 162.8, 169.7, 175.6.Anal. Calcd for C13H20N4O3S: C, 49.98; H, 6.45. Found: C, 50.08;H, 6.59.

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Juskenas, Robertas; Masevicius, Viktoras; Tumkevicius, Sigitas; Synthesis; vol. 45; 17; (2013); p. 2438 – 2446;,
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Reference of 1535-75-7, The chemical industry reduces the impact on the environment during synthesis 1535-75-7, name is 2-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

Synthesis of2-chloro-5-methoxy-N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine [0342] To a stirred solution of 2, 4-dichloro-5-methoxypyrimidine (5 g, 28.08 mmol) in tertiary butyl alcohol (35 mL) under argon atmosphere were added 2-(trifluoromethoxy) aniline (4 g, 22.47 mmol) and diisopropylethylamine (35 mL) at RT. The reaction mixture was stirred at 160 C for 48 h in a sealed tube. After completion of the reaction (monitored by TLC), the volatile components were removed in vacuo. The crude material was purified by silica gel column chromatography using 10% EtOAc:hexanes to afford 2-chloro-5-methoxy- N-(2-(trifluoromethoxy) phenyl) pyrimidin-4-amine (2 g, 22%) as a colorless syrup. 1H-NMR (CDCls, 400 MHz): delta 8.64 (d, 1H), 7.79 (s, 1H), 7.72 (br s, 1H), 7.38 (t, 1H), 7.30-7.27 (m, 1H), 7.10-7.07 (m, 1H), 4.00 (s, 3H); LC-MS: 320.3 (M+l); (column; X Select CSH C-18 (50 x 3.0 mm, 3.5 muiotaeta); RT 4.63 min. 0.05% Aq TFA: ACN; 0.80 ml/min); TLC: 15% EtOAc:hexanes {Rf. 0.3).

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

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, 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 349-65-5, Computed Properties of C8H8F3NO

To a solution of phosgene (1.93 M in toluene; 16 mL, 31.4 mmol) in CH2Cl2 (120 mL) at 0 C was added a solution of 2-methoxy-5-(trifluoromethyl)aniline (3.0 g, 15.7 mmol) and pyridine (2.3 mL, 47.1 mmol) in CH2Cl2 (30 mL) dropwise. The resulting mixture was stirred at 0 C for 30 min and at room temp for 3 h, then concentrated under reduced pressure. The residue was diluted with toluene (30 mL), concentrated under reduced pressure, and treated with Et2O. The resulting precipitate (pyridinium hydrochloride) was removed and the filtrate was concentrated under redeuced pressure to give the title compound as a yellow oil (3.0 g) which crystallized upon standing at room temp. for a few days.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Bayer Corporation; EP1449834; (2004); A2;,
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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. 2734-70-5, name is 2,6-Dimethoxyaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2,6-Dimethoxyaniline

To a solution of 2,6-dimethoxyaniline (500 g, 3.25 mol, 1 eq) in DCM (5.0 L) was added 2,6- lutidine (1.5 L, 13.0 mol, 4 eq). The reaction mixture was cooled to 0 C (internal temperature) and CSC12 (374 mL, 4.88 mol, 1.5 eq) was added drop-wise. The reaction mixture was allowed to stir for 2 h. The solvent was then evaporated in vacuo, and the initial mass was purified by Si02 column to provide 2-isothiocyanato-1,3- dimethoxybenzene, Example 28.0 as white solid. LCMS-ESI (pos.) m/z: (M+H) = 196. 1H NMR (400 MHz, CDC13) oe 7.16 (t, J= 8.48 Hz, 1H), 6.55 (d, J= 8.48 Hz, 2H), 3.90 (app s, 6H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); 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. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H14ClNO

Example 52-1 NL- (4-benzyloxyphenyl)-4-methoxybenzamidine To a solutionof 4-benzyloxyaniline hydrochloride (3g) in tetrahydrofuran (15ML), 1.OM sodium bis (trimethylsilyl) amide in tetrahydrofuran (26. 7ML) wasadded dropwise at room temperature. After the mixture was stirred for20min, anisonitrile (1.69g) was added.The reaction mixture was stirred for 4hrs, and then poured into 300ML OFice-water. The precipitates were collected by filtration, washed withdiisopropyl ether to give the target compound (3.3g).1H NMR (200MHZ, DMSO-D6, D) : 3.8 (3H, s), 5.05 (2H, s), 6.09 (2H, bs),6.74-6. 8 (2H, m), 6.96 (4H, d, J=8.5Hz), 7.29-7. 49 (5H, m), 7.92 (2H,d, J=8.9Hz).MS m/e: 333 (M+H) +.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; WO2004/99130; (2004); 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. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H11NO

Starting material Boc-L-phenylalanine (1) (2.90 g, 10.93 mmol, 1.5 eq.),1H-benzotriazol-1-yloxytripyrrolidinyl hexafluorophosphate (5.69 g, 10.93 mmol, 1.5 eq.) was added to 20 mL of dichloromethane and stirred for 30 min under ice bath;Then N,N-diisopropylethylamine (3.61 mL, 21.87 mmol, 3 eq.) was added.And N-methyl-4-aminoanisole (1.0 g 7.29 mmol, 1 eq.),Remove the ice bath and transfer to room temperature for stirring. TLC monitoring; after 6 hours, the reaction is completed.The solvent was distilled off under reduced pressure, and then 40 mL of saturated sodium hydrogen carbonate solution and 40 mL of dichloromethane were added to the residue, and the organic phase was separated and washed with 40 mL of 1N HCl solution.The organic phase was separated and washed with 40 mL of a saturated sodium chloride solution.The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated.The obtained crude product was separated by silica gel column chromatography (eluent EA: PE = 1:8 v/v)Getting an intermediate(S)-(1-((4-Methoxyphenyl)(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamic acid tert-butyl ester (2) crude product 2.48 g, yellow oil, yield 88%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5961-59-1.

Reference:
Patent; Shandong University; Liu Xinyong; Sun Lin; Zhan Peng; Huang Tianguang; Li Guoxiong; Wu Gaoshan; (39 pag.)CN109796418; (2019); A;,
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Reference of 41789-95-1, A common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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: Asolution of the cinnamic acid (5 mmol) and oxalyl chloride (5.5 mmol) in DCM(50 mL) and 2 drops of DMF was stirred at room temperature for 2h, untilevolution of CO2 had ceased.The DCM was removed by rotary evaporation, the residue dissolved in CHCl3(30 mL) and the CHCl3 removed by rotary evaporation to remove anyexcess oxalyl chloride. The residue wasdissolved in DCM (20 mL) and added to a stirred solution of the benzylamine(6.5 mmol) and triethylamine (7 mmol) in DCM (100 mL) at 0 C. The reaction was stirred at room temperaturefor 1h, washed with 2M aq. HCl (30 mL), water (30 mL) and 2M aq. K2CO3(30 mL) and dried (MgSO4). Removal of the solvent gave a solid which was recrystallised fromEtOAc/petroleum ether. (E)-N-(3-Methoxy-benzyl)-N-methyl-3-phenyl-acrylamide 9e. Obtained as a colourles oil (77% yield), spectroscopically identical to the literature.5

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; King, Frank D.; Caddick, Stephen; Tetrahedron; vol. 69; 40; (2013); p. 8592 – 8601;,
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