Month: August 2021

Electric Literature of 7252-83-7,Some common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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.

Step 1: Synthesis of 2-chloro-7-(2,2-dimethoxyethyl)-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidine To a solution of 2-chloro-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidine (650 mg, 2.7 mmol) in DMF (10 mL) were added 2-bromo-1,1-dimethoxyethane (0.65 mL, 5.4 mmol) and Cs2CO3 (1.067 g, 3.3 mmol). The resulting mixture was heated at 80 C. under nitrogen overnight, and cooled to room temperature. Water was added, and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4. The solvent was removed under reduced pressure to give the title compound as light yellow solid (665 mg, 75% yield), which was used in next step without further purification. MS(ESI) m/z 327.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,1-dimethoxyethane, its application will become more common.

Reference:
Patent; Wyeth; US2010/3250; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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. name: 1-Bromo-4-(difluoromethoxy)benzene

A mixture of 1-bromo-4-(difluoromethoxy)benzene (230 mg, 1.05 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (402 mg, 1.58 mmol), PdCl2 (dppf) (20 mg), and Cs2CO3 (682 mg, 2.1 mmol) in dioxane was sealed in a microwave reaction cube and reacted at 180 C. for 2 hours in a microwave reactor. Then it was purified by flash column chromatography (PE/EA) to give the crude compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5905-69-1, its application will become more common.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 4393-09-3, 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. 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: 1-Benzyl-N-(2,3-dimethoxybenzyl)-3-hydroxy-2-oxo-1,2-dihydropyridine-4-carboxamide (J4) The methyl ester J3 (1 equivalent) was heated at 100 C. in 2,3-dimethoxybenzylamine (35 equivalents) overnight. The reaction was cooled, diluted with water and extracted with DCM. The organic phase was dried, concentrated and the residue purified by reverse phase chromatography twice to give the desired amide J4. 1H NMR (CDCl3, 400 MHz,) delta 8.1 (1H, br. s), 7.3 (3H, m), 7.25 (2H, m), 7.0 (2H, m), 6.95 (1H, m), 6.83 (3H, m), 5.14 (2H, s), 4.64 (2H, d, J=5.6 Hz), 3.88 (3H, s), 3.84 (3H, s).

The chemical industry reduces the impact on the environment during synthesis (2,3-Dimethoxyphenyl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P, ANGELETTI S.P.A.; MERCK & CO., INC.; US2007/155744; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, 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 7252-83-7, Application In Synthesis of 2-Bromo-1,1-dimethoxyethane

Dissolve 4-fluorophenol (5.5 g, 49.1 mmol) in acetonitrile (49 mL) and treat the solution with 2-bromo-l, l-dimethoxy ethane (11.6 mL, 98.1 mmol) and K2CO3 (16.95 g, 122.7 mmol). Heat the solution to reflux with stirring for five days. Filter the mixture, and concentrate the filtrate under reduced pressure. Subject the resulting crude material to silica gel chromatography eluting with a gradient of 0% to 50% EtOAc/hexanes. Concentrate the fractions containing the desired product under reduced pressure to furnish the title compound as a colorless oil (5.85 g, 60% yield). Mass spectrum (m/z) 218 (M + NH4)+, 223 (M + Na)+.

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; ELI LILLY AND COMPANY; SCHIFFLER, Matthew Allen; YORK, Jeremy Schulenburg; WO2014/4229; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 202865-80-3, 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 202865-80-3 as follows.

To a mixture of 2-amino-5-[3-(t-butyl)dimethyl-silanoxypropyloxy]-1-(4-methylbenzyl)benzene (54 mg, 0.14 mmol), 4-bromo-2-fluoro-1-isopropoxybenzene (32.6 mg, 0.14 mmol), dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl (3.3 mg, 0.007 mmol), potassium t-butoxide (28.3 mg, 0.29 mmol) and toluene (2 mL) was added palladium acetate(II) (1.6 mg, 0.007 mmol) under nitrogen atmosphere, and the resulting mixture was stirred at 100C for 1 hour. The reaction mixture was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1-(4-chlorobenzyl)-3-[3-(t-butyl)dimethyl-silanoxypropyloxy]-6-(3-fluoro-4-isopropoxy phenylamino)benzene (69 mg, Yield: 92%) as brown oil. 1H-NMR (delta ppm TMS/DMSO-d6): 0.00(6H, s), 0.84 (9H, s), 1.21 (6H, d, J = 6.0 Hz), 1.84 (2H, q, J = 6.0 Hz), 2.22 (3H, s), 3.70 (2H, t, J = 6.0 Hz), 3.80 (2H, s), 3.92 (2H, t, J = 6.0 Hz), 4.27 (1H, q, J = 6.0 Hz), 6.32-6.42 (2H, m), 6.62 (1H, d, J = 3.0 Hz), 6.75 (1H, dd, J = 2.4 Hz, 8.4 Hz), 6.84-6.94 (1H, m), 6.97-7.08 (5H, m), 7.25 (1H, s).

According to the analysis of related databases, 202865-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., SDS of cas: 54314-84-0

To a solution of methyl isobutyrate 23 (5g, 49 mmol) in THF was added slowly a solution of LDA (52 mmol, generated from n-BuLi and diisopropyl amine) in THF at -78 0C, the reaction was stirred for 20 minutes. The resulting solution was treated with a solution of Benzyl 3-bromopropyl ether 22 in HMPA and stirred at -78 0C for 12 h, aq. HCI (1 N) was added and the resulting mixture extracted with ether, Organic layer washed with water, saturated NaHCO3, dried and concentrated, it was purified by to give the desired ester 24 (11.6 g, 80percent). 1HNMR (CDCI3) delta 7.36-7.26 (m, 5H), 4.49 (s, 2H), 3.65 (s, 3H), 3.45 (t, J = 6.5 Hz, 2H), 1.62-1.52 (m, 4H), 1.18 (s, 6H); 13C NMR (CDCI3) delta 178.3, 138.5, 128.3, 127.6, 127.5, 72.8, 70.5, 51.7, 42.0, 37.1 , 25.3, 25.1.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/158381; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 2734-70-5, 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. 2734-70-5, name is 2,6-Dimethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,6-dimethoxyaniline (0.51 g, 3.3 mmol) and 5-methylnicotinonitrile (0.39 g, 3.3 mmol) in toluene (10 ml) at 0° C. was added dropwise TMS-OTf (1.2 ml, 6.5 mmol). The resulting mixture was stirred at 0° C. for 10 min and heated to 110° C. for 2 days. The reaction mixture was cooled to 0° C., quenched with 1N HCl (10 mL) solution and diluted with EtOAc. The organic layer was washed with 1N HCl solution and dried over sodium sulfate, decanted and concentrated to give a brown oil. The residue was added to a silica gel (40 g) column and was eluted with 0-100percent 1percent Et3N/EtOAc in DCM. Collected fractions to give Compound 7a (0.65 g, 73percent yield) as an off white solid. MS m/z=272.2 (M+H). 1H NMR (500 MHz, CHLOROFORM-d) delta 8.90 (s, 1H), 8.56 (s, 1H), 8.24 (s, 1H), 7.07 (t, J=8.3 Hz, 1H), 6.68 (d, J=8.3 Hz, 2H), 4.76 (br s, 2H), 3.84 (s, 6H), 2.43 (s, 3H).

The synthetic route of 2,6-Dimethoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Pi, Zulan; Bilder, Donna M.; Brigance, Robert Paul; Finlay, Heather; Jiang, Wen; Johnson, James A.; Lawrence, R. Michael; Meng, Wei; Myers, Michael C.; Phillips, Monique; Tora, George O.; Zhang, Xiaojun; (59 pag.)US2017/275272; (2017); 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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 768-70-7

A mixture of methyl 4-hydroxy-3-iodobenzoate (0.14 g, 0.50 mmol), 3-ethynylanisole (0.19 mL, 1.50 mmol), bis(triphenylphosphine)palladium(II) chloride (0.035 g, 0.050 mmol), copper(I) iodide (9.5 mg, 0.050 mmol) and 1,1,3,3-tetramethylguanidine (0.63 mL, 5.00 mmol) in N,lambda/-dimethylformamide (5 mL) under an atmosphere of argon was heated at 70 0C for 3 days. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using heptane:ethyl acetate (9:1) as the eluent, gave 0.13 g (91% yield) of the title compound.1H NMR (CDCl3) delta ppm 8.35 (dd, 1 H) 8.04 (dd, 1 H) 7.57 (d, 1 H) 7.49 (ddd, 1 H) 7.37 – 7.45 (m, 2 H) 7.10 (d, 1 H) 6.96 (ddd, 1 H) 3.98 (s, 3 H) 3.93 (s, 3 H); MS (EI) m/z 282 [M]+.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2009/64251; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 452-08-4, The chemical industry reduces the impact on the environment during synthesis 452-08-4, name is 2-Bromo-4-fluoro-1-methoxybenzene, I believe this compound will play a more active role in future production and life.

EXAMPLE 107 9-Fluoro-1,2-dihydro-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 207, structure 41 of Scheme XI, where R1 =H, R2 =F) 5-Fluoro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =F) In a 200-mL flask, a solution of 2-bromo-4-fluoroanisole (Aldrich: 4.00 mL, 30.8 mmol) in THF (50 mL) was cooled to -78 C. (CO2 /IPA). To this solution n-BuLi (Aldrich: 2.5M in hexanes; 12.4 mL, 31 mmol, 1.0 equivuiv) was added dropwise over a 30 min period. The reaction mixture was stirred at -78 C. for 60 min and treated with trimethylborate (Aldrich: 10.5 mL, 92.4 mmol, 3.0 equivuiv). The reaction mixture was allowed to slowly warm to rt, stirred overnight (12 h), and cooled to 0 C. (ice/H2 O). The solution was treated with 5% HCl until the pH reached 6. The reaction mixture was poured into sat’d NH4 Cl (80 mL) and extracted with CH2 Cl2 (3*100 mL). The extracts were washed with sat’d NH4 Cl (1*80 mL), combined, dried (MgSO4), filtered through a pad of Celite, and concentrated to afford 4.90 g (94%) of a white semi-solid. Data for 5-fluoro-2-methoxyphenylboronic acid: 1 H NMR (400 MHz, acetone-d6): 7.47 (dd, J=8.8, 3.3, 1H); 7.17 (m, 1H); 7.05 (dd, J=9.0, 3.9, 1H); 3.93 (s, 3H).

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-4-fluoro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H13NO

Step C: To a solution of the acid (1.85 g, 7.6 mmol) from step B above and N-methyl morpholine (1.5 mL, 13.7 mmol) in dichloromethane (50 mL) at -20 C. was added isobutyl chloroformate (1.2 mL, 9.1 mmol) dropwise. The reaction solution was stirred at -20 C. for 45 minutes and then a solution of 3-(methoxybenzyl) methylamine (1.3 g, 8.4 mmol) in dichloromethane (10 mL) was added to it dropwise. The resultant solution was warmed to room temperature and stirred overnight. The reaction solution was then washed with water, saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (95:5 to 50:50 hexanes/ethyl acetate) to give the desired product (2.0 g, 78%) as a yellow oil: 1H NMR (CDCl3, 500 MHz) delta 7.96-7.86 (m, 3H), 7.59-7.37 (m, 2H), 7.34-7.26 (m, 2H), 7.04-6.78 (m, 4H), 4.70 (d, J=13.5 Hz, 2H), 3.80 (s, 3H), 3.10 (d, J=17.9 Hz, 3H).

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; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem