Month: June 2021

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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H7F2NO

4-(Difluoromethoxy)aniline (1 g, 6.28 mmol) was dissolved in aqueous hydrochloric acid (12%, 7.35 ml, 25.1 mmol). The solution was cooled to 0 C. and sodium nitrite (434 mg, 6.28 mmol) dissolved in water (2 ml) was slowly added at a temperature below 5 C. After being stirred at 0 C. for 30 min, a solution of ethyl isocyanoacetate (711 mg, 6.28 mmol) and sodium acetate (5.16 g, 62.8 mmol) in MeOH (20 ml) and water (6 ml) was slowly added dropwise at the same temperature. The reaction mixture was stirred for 2 h at 0 C. The solvent was evaporated, 1 M hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic phase was washed with sodium bicarbonate solution and brine and dried with MgSO4. After chromatography (Silica gel, 40 g, 50% EtOAc in heptane) 220 mg ester was obtained that was dissolved in a mixture of tetrahydrofuran (2 ml), methanol (1 ml) and water (1 ml). Lithium hydroxide hydrate (97.8 mg, 2.33 mmol) was added and the solution was heated to 80 C. for 2 h. The solvent was removed under reduced pressure. The residue obtained was dissolved in 1 M hydrochloric acid and the solution was extracted with ethyl acetate twice. The combined organic layers were dried over MgSO4 and evaporated. The orange solid was recrystallized in a mixture of heptane and ethyl acetate (4:1). 121 mg (7%) of an off-white solid was obtained. 1H NMR (300 MHz, CDCl3) ? ppm: 7.34 (t, 1H; J=73 Hz), 7.41 (d, 2H; J=8.7 Hz), 7.95 (d, 2H; J=8.7 Hz), 9.38 (s, 1H).

According to the analysis of related databases, 22236-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; Galley, Guido; Ghellamallah, Cedric; Norcross, Roger; Pflieger, Philippe; US2015/191458; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 62415-74-1, name is 1,2-Dibromo-4-methoxybenzene, 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 62415-74-1, Product Details of 62415-74-1

General procedure: Into a dried two-necked flask (50 mL) equipped with a condenser were placed a stirrer bar, Mg powder (99.9%, 8 mmol), LiCl (8 mmol),DMI (10 mL), and chlorotrimethylsilane (16 mmol). After stirring the mixture at rt for 15 min, 1,2-dibromoarene (1 mmol) was added and the mixture was stirred for 4 h. The mixture was quenched with sat.NaHCO3 and the resulting precipitates were filtered off. The filtrate was extracted with hexane (3 ×) and the combined organic extracts were washed with brine, dried (anhyd Na2SO4), and concentrated by a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexane or hexane/CH2Cl2).

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

Reference:
Article; Kitamura, Tsugio; Yamada, Rin; Gondo, Keisuke; Eguchi, Nobuo; Oyamada, Juzo; Synthesis; vol. 49; 11; (2017); p. 2495 – 2500;,
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These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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. category: ethers-buliding-blocks

In an open ChemGlass vial with pressure -release top, a stirred mixture of 3- bromobenzaldehyde diethylacetal (Aldrich, St. Louis, MO) (65 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′- diisopropoxybiphenyl (23 mg, 0.05 mmol), K2C03 (138 mg, 1.0 mmol) and trans-2- (trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H20 (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100 C and stirred overnight. After allowing to cool, the reaction mixture was diluted with H20 (15 mL) and EtO Ac (20 mL), filtered through Celite and the filter cake washed with EtO Ac (2 x 20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2 x 15 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (3 prep TLC plates used) using EtOAc / hexane (1:4) as eluent to give the product (58.6 mg, 69% – yield adjusted for purity) as an oil [note: desired product contaminated with another compound after prep TLC – approximately 85% pure by 1H NMR and LC/MS].[00221] 1H NMR (CDC13, 300MHz): delta 7.34-7.24 (m, 3H), 7.08 (dt, / = 7.1, 1.7 Hz, 1H), 5.46 (s, 1H), 3.67-3.48 (m, 4H), 2.40-2.34 (m, 1H), 1.88-1.75 (m, 1H), 1.40-1.31 (m, 1H), 1.24 (t, 7 = 7.1 Hz, 6H), 1.20-1.14 (m, 1H). 19F NMR (CDC13, 282 MHz): -66.8 (d, / = 6.8 Hz), m/z = no mass-ion by LC/MS or HRMS.

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DUNCTON, Matthew; SINGH, Rajinder; WO2012/75316; (2012); 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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H11BrO

To a flame-dried Schlenk tube containing CpFe(CO)2Cl (6) (10.3 mg, 0.05 mmol),3-bromopropyl phenyl ether (1j) (223 mg, 1.04 mmol), THF (0.25 mL), n-BuMgCl (2a)(2M in THF, 0.75 mL, 1.5 mmol), and 1,3-butadiene (90 mL as gas, 4.0 mmol) wereadded successively at ?78 C followed by stirring at 0 °C for 2 h and rt for 22 h. Thereaction was quenched by the addition of sat NH4Cl aq., extracted with Et2O (10 mL x3), concentrated, and purified by PTLC (eluent: hexane/Et2O = 99/1) to obtain heptylphenyl etherS2 (3ja) as yellow oil (79.5 mg, 40percent).

According to the analysis of related databases, 588-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwasaki, Takanori; Shimizu, Ryohei; Imanishi, Reiko; Kuniyasu, Hitoshi; Kambe, Nobuaki; Chemistry Letters; vol. 47; 6; (2018); p. 763 – 766;,
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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. 707-07-3, name is (Trimethoxymethyl)benzene, A new synthetic method of this compound is introduced below., Product Details of 707-07-3

To toluene (200 mL), 5-bromo-2-amino-benzylamine (9.5 g, 47.2 mmol) and trimethyl- benzoic orthoester (8.2 g, 47.2 mmol) were added, followed by p-toulensulfonic acid (1.35 g, 7.1 mmol). The resulting suspension was stirred at reflux for 50 hours. The reaction mixture was cooled at r.t., diluted with AcOEt (150 mL), washed with saturated sodium bicarbonate, then with water. The organic layer was dried and concentrated to provide the intermediate dihydroquinazoline as a light brown solid (8.5 g; 63%). This intermediate is dissolved in DCM (20 mL) at r.t., then MnO2 (5.1 g ) was added. The resulting mixture was stirred at r.t. for 48 hrs, then filtered on celite. The filtrate was concentrated to provide the title product as white solid ( 8.1 g, 95%). Cj4H9BrN2; MW: 285.15; MS m/z: 286 (M+ 1). 1H-NMR (300 MHz, d6-DMSO) ppm: 7.58-7.61 (m, 3H), 8.02 (d, IH), 8.17 (dd, IH), 8.49-8.56(m, 3H), 9.70(s, IH).

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; ROTTAPHARM S.P.A.; WO2009/152868; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, 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 13321-74-9, category: ethers-buliding-blocks

General procedure: NaOt-Bu (0.240 g, 2.5 mmol), Pd(OAc)2 (0.006 g, 0.025 mmol) and [HPt-Bu3][BF4] (0.010 g, 0.035 mmol) were suspended in toluene (3 ml) in a 5 ml microwave vial. The appropriate 2-chloroaniline (0.50 mmol) and aryl bromide (0.50 mmol) were then added and the vial sealed. The reaction was then heated in the microwave reactor at 160 C for 3 h, allowed to cool, and then quenched by addition of aqueous HCl (2 M, 3 ml). The organic phase was extracted with CH2Cl2 (2×20 ml), dried (MgSO4), then filtered and the solvent removed under reduced pressure. The crude product mixture was then subjected to column chromatography (SiO2).

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:
Article; Bedford, Robin B.; Bowen, John G.; Weeks, Amanda L.; Tetrahedron; vol. 69; 22; (2013); p. 4389 – 4394;,
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Electric Literature of 2734-70-5, The chemical industry reduces the impact on the environment during synthesis 2734-70-5, name is 2,6-Dimethoxyaniline, I believe this compound will play a more active role in future production and life.

A slurry of 398.1 (5.31 g, 28.7 mmol) and potassium hydroxide (3.06 g, 54.5 mmol) in water (20.5 mL) was heated at reflux for 1.25 h. The reaction was allowed to cool to RT and then 3 N HCl was added until the pH was 2. The mixture was extracted with EtOAc (4X). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to afford 398.2 (3.76 g, 83percent yield) as a light yellow oil. Note that 398.2 contains 35percent of the corresponding decarboxylation byproduct 4-ethylthiazole. Yhis mixture was used in the subsequent step. An ice-cooled solution of 398.2 (3.70 g, 65percent pure, 15.3 mmol) in DMF (55 mL) was treated with TEA (5.95 mL, 42.8 mmol) followed by HATU (7.0 g, 18.4 mmol) directly. After 5 min, 2,6-dimethoxyaniline (Amfinecom Inc., 2.3 g, 15.3 mmol) was added. The resulting brown solution was warmed to RT and stirred for 1.75 h. The reaction was then partitioned between water (275 mL) and EtOAc (2X). The combined organic layers were washed with water (1X) and brine (1X), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gelchromatography (eluent: 10-100percent EtOAc in hexanes) to provide Example 398.3 (2.54 g, 57percent yield) as a light yellow solid. LCMS-ESI (pos.) m/z: 293.0 (M+H)+.

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, 2,6-Dimethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
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Reference of 768-70-7, A common heterocyclic compound, 768-70-7, name is 3-Ethynylanisole, molecular formula is C9H8O, 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: Preparation of Copper Acetylides; Procedure 1To a solution of CuI (3.8 g, 20.0 mmol) in a mixture of NH4OH(28% NH3 solution, 50 mL) and EtOH (30 mL) was added the alkyne1 (10.0 mmol) dropwise. The deep blue reaction mixture wasstirred overnight at r.t. under argon and the yellow precipitate wascollected by filtration and successively washed with NH4OH (10%NH3 solution, 3 × 50 mL), H2O (3 × 50 mL), EtOH (3 × 50 mL), andEt2O (3 × 50 mL). The bright yellow solid was then dried under highvacuum overnight to afford the desired polymeric copper acetylide2, which was used without further purification.

The synthetic route of 768-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Theunissen, Cedric; Lecomte, Morgan; Jouvin, Kevin; Laouiti, Anouar; Guissart, Celine; Heimburger, Jeremy; Loire, Estelle; Evano, Gwilherm; Synthesis; vol. 46; 9; (2014); p. 1157 – 1166;,
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Reference of 6096-89-5, 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 6096-89-5 as follows.

Example 167. N-(3-(3,4-dichlorophenyl)propyl)-l-(2-(4-fluorophenoxy)ethyl)-4- h drox -5 -oxo-2,5 -dihydro- 1 H-pyrrole-3 -carboxamide[00219] To a solution of 2-(4-fluorophenoxy)ethanamine (0.022 g, 0.14 mmol) in MeOH (3 mL) was added DIPEA (0.024 mL, 0.14 mmol). The mixture was stirred for 5 min at rt, then paraformaldehyde (4.19 mg, 0.140 mmol) was added. The mixture heated at 60 C for 10 min using microwave irradiation. The reaction was cooled to rt, then Intermediate 5 (50 mg, 0.140 mmol) was added in a single portion. The reaction mixture was heated at 100 C for 15 min using microwave irradiation, then stirred at rt for 16 h. The reaction mixture was diluted with MeOHiH^O (9: 1) containing 0.1 % TFA, then purified by RP preparative HPLC (Method C) to obtain 9.2 mg (14% yield) of Example 167. HPLC/MS (Method C) RT = 3.35 min, [M+H]+ 468; .H NMR (500 MHz, methanol-^) (delta ppm): 1.83-1.95 (m, 2 H), 2.66 (t, J=7.70 Hz, 2 H), 3.36 (t, J=6.87 Hz, 2 H), 3.85 (t, J=5.22 Hz, 2 H), 4.11-4.20 (m, 4 H), 6.91 (d, J=4.40 Hz, 1 H), 6.93 (d, J=3.85 Hz, 1 H), 6.99 (t, J=8.80 Hz, 2 H), 7.14 (dd, J=8.25, 2.20 Hz, 1 H), 7.35-7.41 (m, 2 H).

According to the analysis of related databases, 6096-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ABELL, Lynn; ADAM, Leonard; CAVALLARO, Cullen L.; FINLAY, Heather; FRIENDS, Todd J.; HANGELAND, Jon J.; JIANG, Ji; LAWRENCE, R. Michael; LLOYD, John; PI, Zulan; TORA, George O.; QIAO, Jennifer X.; HU, Carol Hui; WANG, Tammy C.; WO2013/48982; (2013); A1;,
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91-16-7, name is 1,2-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. Quality Control of 1,2-Dimethoxybenzene

Preparation A 1,2-dibromo-4,5-dimethoxybenzene 16.16 g of 1,2-dimethoxybenzene (117 mmol) are stirred at 0 C. in CCl4 (120 mL). 13.2 mL of dibromine (2.2 eq; 257.4 mmol; 41.13 g) dissolved in CCl4 (25 mL) are added dropwise (30 min) whilst monitoring the temperature (0-5 C.) [Fit an outlet which bubbles into a solution of Na2CO3 in order to neutralise the hydrobromic acid which forms]. After stirring for 2 hours at 0 C., the reaction mixture is then poured onto a mixture of water+ice, and the organic phase is washed with aqueous 10% NaHSO3 solution and then with aqueous 10% NaOH solution. After evaporation and drying, 33.42 g of a white solid corresponding to the title product are obtained. Yield=97% m.p. 92-93 C. 1H NMR (CDCl3): delta=7.06 (s; 2H); 3.86 (s; 6H). 13C NMR (CDCl3): delta=148.8; 115.9; 114.7; 56.2.

The synthetic route of 91-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Les Laboratoires Servier; Vaysse-Ludot, Lucile; Le Flohic, Alexandre; Vaultier, Michel; Pucheault, Mathieu; Kaminski, Thomas; US8859763; (2014); B1;,
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