Tag: M.W=200-300

Reference of 22094-18-4, A common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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.

Example 129A 3,3-dimethoxy-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarboxamide 2-[4-(Trifluoromethoxy)phenyl]acetonitrile (7.86 mL, 50 mmol), 1,3-dibromo-2,2-dimethoxypropane (13.10 g, 50.0 mmol), and sodium tert-butoxide (10.57 g, 110 mmol) were dissolved in DMSO (100 mL) and water (5 mL), and the mixture was heated for 1 hour at 125 C. The reaction was cooled to ambient temperature and stirred overnight. The reaction mixture was diluted with water and extracted three times with diethyl ether. The combined organic layers were washed with brine, dried with MgSO4, filtered, and concentrated to give the title compound (17.02 g, 53.3 mmol, 107% yield). MS (DCI+): m/z 320.1 (M+H), 337.1 (M+NH4). 1FINMR (300 MHz, DMSO-d6) delta 7.44 (d, J=8.8 Hz, 2H), 7.34 (s, 1H), 7.31 (d, J=8.8 Hz, 2H), 6.90 (s, 1H), 3.05 (s, 3H), 3.02-2.93 (m, 5H), 2.41 (d, J=13.4 Hz, 2H).

The synthetic route of 22094-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2014/80803; (2014); 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. 458-50-4, name is 4-Bromo-3-fluoroanisole, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Bromo-3-fluoroanisole

A mixture of 4-bromo-3-fluoro anisole (2.0 g, 9.75 mmol), methyl 3-methyl-4-(4,4,5,5- tetramethyl-1-3s2-dioxaborolan-2-yl)benzoate (2.8 g, 10.14 mmol), Cs2C03 (6.99 g, 21.46 mmol) and catalytic amount of Pd(PPh3)4 (1.13 g, 0.975 mmol) in dioxane (50 mL) was stirred at 80 °C overnight. The solvent was removed. Water was added. The mixture was extracted with CH2C12 (3 x 20 mL). Washed with brine and dried over Na2SC>4.The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/hexane (1:9) to give the title compound as a colorless solid.

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; MERCK SHARP & DOHME CORP.; LU, Zhijian; CHEN, Yi-Heng; SMITH, Cameron; LI, Hong; THOMPSON, Christopher, F.; SWEIS, Ramzi; SINCLAIR, Peter; KALLASHI, Florida; HUNT, Julianne; ADAMSON, Samantha, E.; DONG, Guizhen; ONDEYKA, Debra, L.; QIAN, Xiaoxia; SUN, Wanying; VACHAL, Petr; ZHAO, Kake; WO2012/58187; (2012); A1;,
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Related Products of 1112210-82-8,Some common heterocyclic compound, 1112210-82-8, name is 1,3-Dibromo-5-isopropoxybenzene, molecular formula is C9H10Br2O, 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.

Synthesis of Intermediate 2)Molecular Weight: 293.98 Molecular Weight: 186.21[00530] In a 3-neck 100 mL round-bottomed flask, intermediate- 1 (3.5 g, 1 eq.) was dissolved in DMF and degassed it for 20-30 min. To this reaction mixture, Zinc Cyanide (1.72 g, 1.2 eq.) and tetrakis (0.705 g, 0.05 eq.) was added. Resulting reaction mixture was stirred at 80-90C and reaction was monitored by TLC using Ethyl acetate: hexane (1 :9) as mobile phase, which shows starting material was consumed after 5 h. Reaction was quenched into ice-water slurry and compound was extracted using ethyl acetate (50 mL x 3), combined organic layer were dried over anhydrous sodium sulfate and concentrated under reduce pressure to give crude compound. The crude material was subjected to column chromatography using silica 60/120 as stationary phase and ethyl acetate :n-Hexane as mobile phase. Compound was eluted in 7% ethyl acetate in Hexane. Fractions containing compound was distilled out using rotary evaporation at 40 C/250 mm Hg to obtain 2.095 g (94.51%). Mass/LCMS: LC-MS purity 92.36%, NMR: Confirmed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-isopropoxybenzene, its application will become more common.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SHECHTER, Sharon; KAUFFMAN, Michael; SANDANYAKA, Vincent, P.; SHACHAM, Sharon; WO2011/109799; (2011); 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. 116557-46-1, name is 3-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H8BrNO

Step 3[00174j IntlO (2.0 g, 9.9 mmol) was dissolved in dioxane (40 mL) and the vessel purged with nitrogen for 5 minutes. Next bis(pinacolato)diborone (3.77 g, 14.85 mmol), [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (404 mg, 0.49 mmol) and potassium acetate (2.91 g, 29.7 mmol) were added. The flask was evacuated and backfilled with nitrogen, and then heated to 100 Cfor 15 hours. Water was added to quench the reaction and the product was then extracted with EtOAc. The combined organic layers were washed with brine (x3), dried over sodium sulfate, filtered, concentrated and purified using automated chromatography (elutes at 40% ethyl acetate) to provide Intl 1 (2.0 g, 8 1%). ?H NMR (400MHz, chloroform-d) oe 7.12 (dd,J=7.3, 1.8 Hz, 1H), 6.96-6.89 (m, 1H), 6.88-6.83 (m, 1H),3.82 (s, 3H), 1.37 (s, 12H). LC retention time 0.65 [J]. m/z: 250 (MHj.

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 116557-46-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; TOKARSKI, John S.; KUMAR, Amit; WO2014/74661; (2014); A1;,
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These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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. Recommanded Product: 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

(b) tert-Butyl1-(trifluoroacetyl)azetidine-3-carboxylate 1,1-di-tert-butoxy-N,N-dimethylmethanamine (16.5 g, 81 mmol) was added to a solution of 1-(trifluoroacetyl)azetidine-3-carboxylic acid (5 g, 25 mmol) and the mixture was heated to reflux for 8 hours. LC-MS showed remaining starting material and therefore an additional amount of 1,1-di-tert-butoxy-N,N-dimethylmethanamine (21.2 g, 81 mmol) was added and the heating was continued over night. LC-MS showed still some remaining starting material (starting material/product about 1/2) and the THF was exchanged for toluene (100 mL) and the mixture heated to 100 C. (oil bath temperature) for 2 hours. The solvent was evaporated and the residue dissolved in EtOAc (200 mL). The organic phase was washed with NaHCO3(sat) (2*50 mL), water (2*50 mL), Brine (50 mL), dried (Na2SO4), filtered and evaporated to give the desired product. Yield: 4.5 g (70%).

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US2008/171732; (2008); A1;,
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Application of 17715-69-4, These common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, 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 suspension of Pd2(dba)3 (6.9mg, 0.0075mmol), tBu3PHBF4 (8.7mg, 0.03mmol), KOH (42mg, 0.75mmol), aryl bromide 4 (0.36mmol) and tetralone 3 (0.3mmol) in a mixture of dioxane/water (4:1, v/v, 3mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100°C, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography. Dioxane quality is extremely important for the success of the reaction. Characterization of alpha-aryl-alpha-tetralones is given in Ref.[26].

Statistics shows that 1-Bromo-2,4-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 17715-69-4.

Reference:
Article; Fernandes, Talita de A.; Costa, Paulo R. R.; Manvar, Dinesh; Basu, Amartya; Kaushik-Basu, Neerja; Domingos, Jorge L. O.; Nichols, Daniel Brian; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 33 – 38;,
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Synthetic Route of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

10.0 g (0.049 mol) of 4-bromo-2-methoxyaniline in a three-necked flask,Take 13.0 g (0.060 mol) of di-tert-butyl dicarbonate,It was dissolved in tetrahydrofuran.After reacting for 5 hours at 40 C., the solvent is distilled off and represented by the formula (K-1)14.7 g of compound was obtained.

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-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DIC Corporation; Horiguchi, Masahiro; Hayashi, Masanao; Kusumoto, Tetsuo; (46 pag.)JP5888544; (2016); B2;,
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Reference of 106854-77-7, The chemical industry reduces the impact on the environment during synthesis 106854-77-7, name is 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene, I believe this compound will play a more active role in future production and life.

Step 7: 1 -Benzyl-N,4-dimethyl-N-neopentyl-3-(4-(2,2,2-trifluoroethoxy)phenyl)-5- (trifluoromethyl)-1 H-pyrrole-2-carboxamide (SC-260)Under an nitrogen atmosphere 1 -benzyl-N,4-dimethyl-N-neopentyl-3-(4,4,5,5-tetramethyl-1 3,2- dioxaborolan-2-yl)-5-(trifluoromethyl)-1 H-pyrrole-2-carboxamide (106 mg, 0.216 mmol) was dissolved in DMF (1 mL) and L1OH (4 mg, 0.216 mmol), bis(tri-tert-butylphosphine)palladium (0) (6 mg, 0.014 mmol) and 1-bromo-4-(2,2,2-trifluoroethoxy)benzene (50 mg, 0.196 mmol) were subsequently added. The reaction mixture was stirred at 80C under microwave irridation for I h. The mixture was cooled to RT and the reaction was stopped by addition of 1 M NaOH solution (2 mL). The crude product was extracted with EtOAc (2×3 mL) and the combined organic layers were washed with water (3×1 mL), dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude mass was purified by flash chromatography to give SC-260 (95 mg, 89.7 %).

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-Bromo-4-(2,2,2-trifluoroethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; STEINHAGEN, Henning; DAMANN, Nils; SKONE, Philip; HAMLYN, Richard; KIRBY, Robert; ROGERS, Marc; SUTTON, Kathy; WO2014/32801; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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 36805-97-7, Product Details of 36805-97-7

A solution of (S)-(+)-Z-4-amino-2-hydroxybutyric acid (5) (5 g, 19.74 mmol) in toluene (38 mL) containing N,N-dimethylformamide di-tert-butyl acetal (18.92 mL, 78.96 mmol) was heated to 95C for 3 h. The solvent was then evaporated and the crude product was purified by flash chromatography on silica gel (n-hexane/EtOAc = 7:4) to give (6) (3.4 g, 55.7 % yields) as yellow solid. Mp 42-44C; [alpha]20D= – 5.9 (c= 10.1 mg/ml, CHCl3) 1H-NMR (CDCl3) delta: 1.47 (s, 9H); 1.76-1.85 (m, 1H); 1.94-2.09 (m, 1H); 2.74 (br s, 1H); 3.36 (dd, J= 6.04 Hz, J= 11.99 Hz, 2H); 4.10 (dd, J= 4.02 Hz, J= 8.05 Hz, 1H); 5.09 (s, 2H); 5.21 (br s, 1H); 7.31-7.37 (m, 5H) Anal. Calcd. for C16H23NO5: C, 62.12; H, 7.49; N, 4.53. Found: C, 62.22; H, 7.48; N, 4.53.

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; Bracco Imaging S.p.A; EP2149568; (2010); 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. 4463-59-6, name is 1-(2-Bromoethoxy)-2-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-(2-Bromoethoxy)-2-methoxybenzene

36 g(0.156 ml) of 2-(methoxyphenoxy)ethylbromide and 27.3 grams (0.186 mole) of phthalimide are dissolved in 100 ml of dimethylacetamide, and stirred with heat for diffusion to 90 C. After 30 minutes, 10.45 g(0.186 mole) of potassium hydroxide is dissolved in 30 ml of methanol solution for heating and diffusing over 1.5 hours. Upon cooling, the mixed solution is poured into 300 ml of water. After filtrating the extracted solids, 200 ml of 10% potassium carbonate solution is added, and stirred with heat. The paste-like substance obtained is filtrated. After rinsing with tap water several times, moisture-free alcohol is used for re-crystallization until while crystallization is obtained. 21 grams(0.071 mole) of the above product and 3.55 grams (0.071 mole) of hydrazine hydrate are dissolved in 70 ml of moisture-free alcohol, and upon heating and diffusing for 45 minutes, 20 ml of 18% hydrochloric acid is added into the mixture to continue the diffusion for one hour before cooling. After filtration, the residue obtained from reduction is mixed with 20% of sodium hydroxide for alkalization. Chloroform is used for extraction, and upon filtration and pressurized reduction, it is filled into the silicone tube for separation, while using ethyl acetate as the diluent to obtain an oily product, i.e. 2-(2-methoxy-phenoxy)ethylamine.

The synthetic route of 4463-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Ing-Jun; US2001/56211; (2001); A1;,
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