Month: August 2021

Electric Literature of 39021-83-5, The chemical industry reduces the impact on the environment during synthesis 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, I believe this compound will play a more active role in future production and life.

General procedure: A 100-mL round-bottomed flask was charged with 6 g of silica gel and set up tostir vigorously. Then, a solution of 2.75 g of cerium ammonium nitrate (CAN) (5.0mmol) in water (2.5 mL) was added dropwise. The stirring continued until a freeflowingyellow solid was obtained. DCM (25 mL) was then added to the flask. Thecorresponding substrates where dissolved in 2 mL of DCM and added to the stirredreaction mixture. The reaction was monitored by TLC and after complete consumptionof the starting materials the mixture was filtered through a sintered-glass funnel. Thesolid was washed with about 75 mL of DCM. After solvent removal the quinones wereobtained with high purity. 2,3-Dimethyl-1,4-benzoquinone (46): 1,4-dimethoxy-2,3-dimethylbenzene(43)6 (1 mmol, 166 mg) was used. 46 was obtained without the need of purification (85mg, 63% yield) as an orange powder; m.p. (C) = 54.9-56.4 (Petrol/CH2Cl2); HRMS(EI+): 136.0569 [M]+. Cald. for [C8H8O2]: 136.0524; 1H NMR (400 MHz, CDCl3) delta:6.70 (s, 2H), 2.01 (s, 6H); 13C NMR (100 MHz, CDCl3) delta: 187.4, 141.0, 136.2, 12.2.Data are consistent with those reported in the literature.

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, 1,4-Dimethoxy-2,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jardim, Guilherme A.M.; Silva, Thaissa L.; Goulart, Marilia O.F.; de Simone, Carlos A.; Barbosa, Juliana M.C.; Salomao, Kelly; de Castro, Solange L.; Bower, John F.; da Silva Junior, Eufranio N.; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 406 – 419;,
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Synthetic Route of 929-75-9, These common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, 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: A two-neck flask equipped with a magnetic stirrer and reflux condenser, flushed with dry argon, was charged with diazacrown derivative 4-9 (0.2-0.25 mmol), Pd(dba)2 (8-16 mol%), BINAP or DavePhos ligand (9-18 mol%), absolute dioxane (10-12 mL), the reaction mixture was stirred for several minutes, then the corresponding polyamine (0.2-0.25 mmol) and NaOt-Bu (0.6-0.75 mmol) were added, and the reaction mixture was stirred at reflux for 24 h. After cooling down to room temperature the residue was filtered off, washed with CH2Cl2 (5-10 mL), the combined organic fractions were evaporated in vacuo, the residue was dissolved in CH2Cl2 (10 mL), washed with distilled water (3 × 10 mL), dried over 4A molecular sieves, and the solvent was evaporated in vacuo. The solid residue was chromatographed on silica gel (40-60 mum) using a sequence of eluents: CH2Cl2, CH2Cl2-MeOH 100:1-3:1, CH2Cl2-MeOH-NH3(aq) 100:20:1-10:4:1.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yakushev, Alexei A.; Chernichenko, Nataliya M.; Anokhin, Maxim V.; Averin, Alexei D.; Buryak, Alexei K.; Denat, Franck; Beletskaya, Irina P.; Molecules; vol. 19; 1; (2014); p. 940 – 965;,
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Synthetic Route of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

4-Hydroxy phenyl acetic acid-t-butyl ester (Reagent E) A stirred suspension of 4-hydroxy-phenyl acetic acid (0.152 g, 1 mmol) in anhydrous toluene (5 mL) was heated at 80 C. and N,N-dimethyl formamide-di-t-butyl acetal (1 mL, 4.17 mmol) was added when the solution became homogenous. After 0.5 h, the reaction mixture was cooled to ambient temperature and the volatiles were distilled off in vacuo. The residue was diluted with water and extracted with diethyl ether (*2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 16% ethyl acetate in hexane as the eluent to afford the title compound as a solid (0.11 g, 56%). 1H-NMR (300 MHz, CDCl3): delta1.44(s, 9H), 3.45(s, 2H), 6.55(s, 1H), 6.69(d, J=8.8 Hz, 2H), 7.06(d, J=8.5 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; Allergan Sales, Inc.; US6313107; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, 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 887581-09-1, Application In Synthesis of (2-Bromo-5-methoxyphenyl)methanamine

General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 × 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

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

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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102-52-3, name is 1,1,3,3-Tetramethoxypropane, 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

Stage 5- Preparation of 3-(phenylamino)allylidene)aniline hydrochloride (Bioorg. Med. Chem. 2006, 4, 92-97). Compound having formula (VI) where n=1. 24.7 g of aniline in solution in 300 mL of 0.75 N HCl is added drop by drop to 21.8 g of 1,1,3,3-tetramethoxypropane in solution in 300 mL of 0.75 N HCl. The appearance of an intense orange colour and the precipitation of an orange crystalline solid are observed. The medium is then left under stirring for 3 hours at 50 C. The cooled medium is filtered, vacuum-dried to obtain 15.2 g of orange solid (Yd=44.2%). C15H14N2, HCl-(Mass ESI+400 C. MH+=223.1).

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); PIERRE FABRE MEDICAMENT; Guminski, Yves; Imbert, Thierry; Pesnel, Sabrina; Pillon, Arnaud; Le Pape, Alain; Lerondel, Stephanie; US2013/183247; (2013); A1;,
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Reference of 393-15-7,Some common heterocyclic compound, 393-15-7, name is 4-Methoxy-3-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

4-Methoxy-3-trifluoromethyl-phenylamine (5 g, 26 mmol) in 12 mL water was cooled to -5 degrees C. (Ice/Methanol bath). Conc. HCl was added dropwise (7 ml), and the reaction mixture was stirred for five minutes. A solution of NaNO2 (2.0 g, 29 mmol) dissolved in 3 ml water was added dropwise over 10 minutes, and the reaction mixture was stirred for 30 min. Sodium acetate (1.8 g, 22 mmol) was then added, and stirring was continued at -5 degrees C. In a separate flask, ethyl alpha-acetoacetate (4.55 g, 29 mmol) in 20 ml absolute ethanol was stirred, and KOH (1.6 g, 29 mmol) dissolved in 3 ml water was added, followed by ice (30 g). The resulting diazonium salt was added quickly to the reaction mixture, rinsing in with 5 ml EtOH, and the reaction mixture was stirred at zero degrees C. for 3.5 hours, then stored at -10 C) for 16 hours. The reaction mixture was warmed to room temperature and extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. Solvent was removed under reduced pressure to leave a liquid residue. In a separate flask 100 ml EtOH and 21 ml acetyl chloride were mixed, with cooling in an ice bath, then heated to 70 degrees C. The liquid residue was added via pipette over 15 minutes to the acetyl chloride solution. This reaction mixture was heated to reflux for 2.5 hours, cooled, evaporated under reduced pressure. The residue was purified by column chromatography (10% ethyl acetate/hexane) to give 3.0 g 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester, 38% as a white solid and triturated with diethyl ether to give 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (1.0 g) as a white solid, and 5-Methoxy-3-methyl-4-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (14%) as a white solid.

The synthetic route of 393-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2007/49609; (2007); 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 22236-10-8

Preparation 9 6-Chloro-N*4*-(4-difluoromethoxyphenyl)-2-methylpyrimidine-4,5-diamine; 4,6-dichloro-2-methyl-pyrimidin-5-ylamine (20.0 g, 110 MoI) was added with stirring to EtOH (80 mL) over 3 minutes to give complete solution. 4-Difluoromethyoxyaniline (18.8 g, 118 MoI) was then added with stirring over 3 minutes. A dark brown solution was observed. EtOH (20 mL) was then added followed by a premixed solution of c.HCI (10 mL) in EtOH (40 mL) at a steady rate over 20 minutes. A slight exotherm up to approx 2O0C was noted. The solution was then warmed to 850C and held at that temperature for 4 hours. The reaction mixture was then cooled to room temperature, and a beige solid precipitated. This reaction mixture was filtered then washed with EtOH (100 ml_) followed by MTBE (3OmL) to remove EtOH traces. The resultant solid was dried in vacuo over the weekend to give the title compound, as the hydrochloride salt, as a beige solid (17.2 g, 45%) 1H NMR (400MHz, CD3OD) delta = 2.55 (s, 3H), 6.89 (t, 1 H), 7.27 (d, 2H), 7.75 (d, 2H) LCMS (System 4) 3.07 mins; m/z (APCI) = 301 [MH+]

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

Reference:
Patent; PFIZER LIMITED; WO2009/144632; (2009); 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., SDS of cas: 450-88-4

To a mixture of magnesium (0.79 g, 32.5 mmol) and lithium chloride (1.52 g, 35.80 mmol) in THF (33 ml) at room temperature was added 1-bromo-4-fluoro-2-methoxybenzene (3.13 mL, 24.39 mmol) and the reaction was stirred at 70 C for 1.5 hr. The reaction was then cooled to 0 C, and Fe(acac)3 (0.574 g, 1.63 mmol) was added. After 1 minute, allyl chloride (1.33 mL, 16.26 mmol) was added and the reaction was stirred at 0 C for 30 min. The mixture was warmed to room temperature over 1 hr and was heated at 70 C overnight. The reaction was cooled and diluted with petroleum ether (100 mL). The reaction was then quenched by the addition of a saturated NH4Cl solution (100 mL). The mixture was filtered through a Celite pad and the layers were separated. The aqueous layer was extracted with petroleum ether (2 x 100 mL) and the combined organic phases were dried over Na2SO4 and carefully concentrated (25 C, 250 mbar). The residue was purified by Isco chromatography (100% pet ether as the eleuent) to provide (E,Z)-4-fluoro-2- methoxy-1-(prop-1-en-1-yl)benzene (2.25 g, 83 % yield) as a colorless oil. This mixture was approximately a 3:1 mixture of E and Z isomers with a trace of the allyl isomer present. This material was used directly in the next step.1H NMR (400 MHz, CDCl3) delta 7.31 (dd, J = 8.3, 6.8 Hz, 1H), 6.65- 6.53 (m, 3H), 6.14 (dq, J = 15.8, 6.6 Hz, 1H), 3.82 (s, 3H), 1.88 (dd, J = 6.6, 1.7 Hz, 3H).19F NMR (376 MHz, CDCl3) delta -113.30.

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; DOW AGROSCIENCES LLC; BUCHAN, Zachary A.; LU, Yu; JONES, David M.; MEYER, Kevin G.; YAO, Chenglin; (110 pag.)WO2018/44996; (2018); A1;,
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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. 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

To a suspension of NaH (120 g , 3.0 mol) in DMF (1 L) was added dropwise diisopropyl malonate (507 g, 2.7 mol) under an Ar atmosphere, and the reactionwas stirred.Compound 29.2(360 g, 1.35 mol) was then added in portionsand the mixturewas heated to reflux for 48 hr.The reaction mixture was poured into water (2 L), and extracted with PE (6 x 1 L). The combinedorganic layers were dried, filteredand concentrated under reduced pressure 15 to give a yellow oil, which was purified by distillation under reduced pressureto yield compound 29.3 (150 g, 45%) as a colorless oil.

According to the analysis of related databases, 22094-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHAOGEN, INC.; LINSELL, Martin Sheringham; AGGEN, James Bradley; DOZZO, Paola; HILDEBRANDT, Darin James; COHEN, Frederick; KASAR, Ramesh Annasaheb; KANE, Timothy Robert; GLIEDT, Micah James; MCENROE, Glenn A.; WO2014/165075; (2014); A1;,
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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. 59557-91-4, name is 4-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 59557-91-4

Intermediate 10 4-Bromo-2-methoxy-N /V-dimethylaniline [00406] Formaldehyde (3.7 mL, 49 mmol, 37% aqueous) and acetic acid (57 uL, 1 mmol) were added to a solution of 4-bromo-2-methoxyaniline (2.0 g, 9.9 mmol) in methanol (10 mL) at 25 C. The mixture was stirred for 2 h, and then sodium cyanoborohydride (3.11 g, 49.5 mmol) was added in portions. The resulting mixture was stirred for 12 h, poured into a saturated NaHC03 solution (40 mL), and then extracted with ethyl acetate (3 x20 mL). The combined organic phases were washed with brine (2×20 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate; 15/1) to give 4-bromo-2-methoxy-N,N-dimethylaniline (2.0 g, 80%) as a brown oil. 1H MR (CDC13): delta 7.02 (dd, 1H), 6.95 (d, 1H), 6.78 (d, 1H), 3.87 (s, 3H), 2.76 (s, 6H); MS: 230.0 [M+H]+.

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 59557-91-4.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
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