Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 32943-25-2, name is 3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepine, belongs to chlorides-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 32943-25-2, Product Details of 32943-25-2

A solution of 3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine (5.00 g, 21.8 mmol) (The Journal of Biological Chemistry (2009) 285, 11, 8363-8374) in toluene (50.0 mL) was treated with chloropropionyl chloride (2.18 mL, 22.9 mmol) and heated to 100 C for 1 h. The mixture was cooled to 25 C, concentrated under N2 stream, dissolved in a minimal amount of toluene and purified by flash chromatography (SiO2, 5-20% ethyl acetate-hexanes) to afford the title compound as an off-white solid (4.74 g, 68%). 1H NMR (600 MHz, CDCl3) (mixture of rotamers) 7.38 (1H, s), 7.29 (2H, br m), 7.25 (1H, m), 7.20 (1H, m), 7.14 (1H, m), 7.06 (1H, d, J = 8.2 Hz), [2H, 3.82 (br m), 3.77 (br m)], [2H, 3.39(br m), 3.33 (br m), 3.29 (t, J = 4.7 Hz)], 2.81 (3H, m), [1H, 2.57(t, J = 6.7 Hz), 2.53 (t, J = 6.8 Hz), 2.50 (t, J = 6.6 Hz)]; LCMS m/z 320.4 ([M + H+], C17H15Cl2NO requires 320.1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepine, and friends who are interested can also refer to it.

Reference:
Article; Kastrinsky, David B.; Sangodkar, Jaya; Zaware, Nilesh; Izadmehr, Sudeh; Dhawan, Neil S.; Narla, Goutham; Ohlmeyer, Michael; Bioorganic and Medicinal Chemistry; vol. 23; 19; (2015); p. 6528 – 6534;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1435-50-3, A common heterocyclic compound, 1435-50-3, name is 2-Bromo-1,4-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

Compound4-(4-(3-ethynyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester (0.20 g) , 0.51 mmol) was suspended in DMF (15 mL), and then Pd(PPh3)2Cl2 (36 mg, 0.051 mmol), CuI (10 mg, 0.051 mmol) and1,4-Dichloro-2-bromobenzene (0.12 g, 0.51 mmol). After the reaction liquid is exchanged for three times (nitrogen),Et3N (1.4 mL, 10.2 mmol) was added. After the reaction solution was stirred at 75 C for 2 hours under a nitrogen atmosphere,The organic layer was concentrated under reduced pressure. EtOAc (EtOAc)The organic phase obtained by liquid separation was dried over anhydrous Na2SO?The residue was subjected to silica gel column chromatography(PE/EtOAc(v/v)=1/2)Purification to give the title compound as a yellow solid(0.17 g, 62%).

The synthetic route of 1435-50-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Xiaobo; Zhou Shiqing; (62 pag.)CN103833753; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, A new synthetic method of this compound is introduced below., Formula: C7H7ClFN

Compound 38. 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid 2-chloro-4-fluoro-benzylamide (B250110) 4-(4-Chloro-phenyl)-thiazole-2-carboxylic acid (61 mg, 0.25 mmol) was dissolved in THF (5 mL), followed by addition of CDI (50 mg, 0.31 mmol). The slurry mixture was stirred at RT for 1 hour. 2-Chloro4-fluorobenzylamine (41 mg, 0.26 mmol) dissolved in THF (2 mL) was added to it. The slurry mixture became a clear yellow solution. The reaction was continued at RT overnight. After removal of the solvent, the residue was washed twice with water (2×10 mL). After filtration, the residue was dissolved in dichloromethane (40 mL) and washed with 0.5 N HCl (20 mL) and water (20 mL). The organic solution was dried over sodium sulfate. Rf value (chloroform, Silica) was 0.55. After filtration through a pad of silica eluted with chloroform, the solvent was removed to afford a semisolid (63 mg, Y=66%).

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; Apogee Biotechnology Corporation; US2007/32531; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3BrClF

EXAMPLE 76 5′-(3-Chloro-4fluorophenyl)-spiro[cyclopentane-1,3′-[3H]indol]-2′(1’H)-one A solution of 3-chloro-4-fluoro-bromobenzene (0.4 cm3, 0.66 g, 3.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1’H)-one-5-yl) boronic acid (1.0 g, 4.7 mmol) and sodium carbonate (1.0 g, 9.4 mmol) in water (5 cm3). The solution was brought to reflux for 18 hours and then cooled to room temperature, poured into 2N NaOH and extracted with EtOAc (*3). The combined extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, EtOAc, hexane) to afford the title compound (0.65 g, 66%) as a pale-yellow solid. mp: 202-204 C.; 1H NMR (DMSO-d6) delta10.4 (s, 1H), 7.9 (dd, 1H, J=2.3, 4.9 Hz), 7.7-7.6 (m, 1H), 7.6 (d, 1H, J=1.5 Hz), 7.5 (s, 1H) 7.4 (d, 1H, J=1.8 Hz), 6.9 (d, 1H, J=8.0 Hz), 2.0-1.9 (m, 8H); MS [M-H]-=314.

According to the analysis of related databases, 60811-21-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6391907; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene

General procedure: A mixture of (4-iodophenyl)(methyl)sulfane (Compound 4A) (500 mg, 2 mmol), 4-bromophenylboronic acid (400 mg, 2 mmol), Na2CCh (636 mg, 6 mmol), and Pd(PPh3)4 (115 mg, 0.1 mmol) in toluene/EtOH/H20 (20/10/4 mL) was stirred at 80 C under nitrogen overnight The mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford Compound 4B. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used. – NMR (CDCb, 500 MHz): d (ppm) 2.52 (s, 3H), 7.32 (d, J= 8.5 Hz, 2H), 7.43 (d, J= 8.5 Hz, 2H), 7.48 (d, J= 8.5 Hz, 2H), 7.55 (d, J= 8.5 Hz, 2H).

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

50638-46-5, name is 4-Bromo-3-chloroanisole, belongs to chlorides-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: chlorides-buliding-blocks

Step 2: (E)-tert-Butyl 3-(4-((E)-2-(2-chloro-4-methoxyphenyl)-2-cyclobutyl-l-(4- morpholinophenyl)vinyl)phen l)acrylate[00401] A mixture of (E)-tert-butyl 3-(4-((Z)-2-cyclobutyl-2-(5,5-dimethyl-l ,3,2-dioxaborinan-2- yl)-l-(4-morpholinophenyl)vinyl)phenyl)acrylate (754 mg, 1.64 mmol), l -bromo-2-chloro-4- methoxybenzene (545 mg, 2.46 mmol), Pd(PPh3)2Cl2(1 15 mg, 0.16 mmol), and KOH (6M, 1.6 mL, 9.9 mmol) in 1 ,4-dioxane (10 mL) was heated to 90C for lh. After cooling, ethyl acetate and brine were added to the reaction mixture and the two layers were separated. The organic layer was washed with more brine, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel to afford 520 mg of the title compound as a yellow foam. 1H NMR (400 MHz, DMSO-d6): delta 7.37-7.33 (m, 3H), 7.1 1 (d, 1H), 7.04 (d, 2H), 6.95-6.90 (m, 5H), 6.82 (m, 1H), 6.34 (d, 1H), 3.74 (m, 4H), 3.71 (s, 3H), 3.42 (m, 1H), 3.13 (m, 4H), 1.87 (m, 3H), 1.67 (m, 2H), 1.46 (m, 1H), 1.43 (s, 9H); LCMS: 586 (M+H)+.

The synthetic route of 50638-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; GOVEK, Steven, P.; KAHRAMAN, Mehmet; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2014/151899; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 20850-43-5, 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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows.

5-Chloromethyl benzo [1,3]dioxol g, 65.7 mmol) was dissolved in Dimethylformamide. Then, potassium carbonate (18.2 g, 131.4 mmol), sodium iodide (10.8 g, 72.27 mmol) and ethyl benzoylacetate (12.5 mNo., 72.27 mmol) were added thereto and stirred for 5 hours at room temperature. The reaction mixture was extracted with ammonium chloride and ether, the organic layer was separated, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 2- benzo [1,3]dioxol-5-ylmethyl-3-oxo-3-phenylpropionate ethyl ester (16.4 g, 76 %). ¹H NMR (200MHz, CDCl3) : No. 7.98-6.69 (m, 3H), 5.90 (s, 2H), 4.56 (t, J=7.4 Hz, 1H), 4.09 (q, J=7.2 Hz, 2H), 3.26 (d, J=7.4 Hz, 2H), 1.13 (t, J=7.2 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis 5-(Chloromethyl)benzo[d][1,3]dioxole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; JEIL PHARM. CO., LTD.; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; CJ CORP.; WO2005/100303; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-3,5-dichlorobenzene

In the environment of nitrogen dissolved in I-20(85 g, 179 mmol) 700 mL of tetrahydrofuran (THF), where the 1-bromo-3,5-dichlorobenzene(48.5 g, 215 mmol) and tetrakis( triphenylphosphine) palladium was stirred into the (2.07 g, 1.79 mmol).Into a saturated potassium carbonate in water (61.8 g, 448 mmol) was heated to reflux at 80 ° C for 7 hours. After the reaction was completed, the reaction solution into water and extracted with dichloromethane (DCM) and then water was removed with anhydrous MgSO4, filter and was concentrated under reduced pressure. Thus separated and purified theresulting residue was purified by flash column chromatography compound to obtain a I-21(72.6 g, 82percent)

According to the analysis of related databases, 19752-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheil Industries Co., Ltd; Lee, Han Ir; Yu, Uhn Sun; Kang, Dong Min; Kang, Uii Soo; Yang, Yong Tak; Oh, Jae Jin; Yu, Dong Gyu; Lee, Sang Sin; Jang, Yuna; Jung, Su Young; Han, Su Jin; Hong, Jin Suk; (59 pag.)KR2015/6758; (2015); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13078-80-3, name is 2-(2-Chlorophenyl)ethanamine, belongs to chlorides-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 13078-80-3, Quality Control of 2-(2-Chlorophenyl)ethanamine

N-(2-Fluoropyrimidin-4-yl)-N-methyl-2-phenylpyrimidin-4-amine (442 mg, 1.5 mmol), 2-(2-chlorophenyl)ethanamine (0.32 mL, 2.25 mmol), and dioxane (7 mL) were mixed in a 25 mL roundbottom flask. The mixture was stirred at 100 C. overnight under nitrogen. The reaction was concentrated by vacuum and quenched with saturated NaHCO3 solution. The white solid was filtered and recrystallized to give N2-(2-chlorophenethyl)-N4-methyl-N4-(2-phenylpyrimidin-4-yl)pyrimidine-2,4-diamine as a white solid. MS m/z 417 (MH)+.

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-(2-Chlorophenyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Andersen, Denise Lyn; Chang, Catherine H.; Falsey, James R.; Frohn, Michael J.; Hong, Fang-Tsao; Liao, Hongyu; Liu, Longbin; Lopez, Patricia; Retz, Daniel Martin; Rishton, Gilbert M.; Rzasa, Robert M.; Siegmund, Aaron; Tadesse, Seifu; Tamayo, Nuria; Tegley, Christopher M.; US2006/69110; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 445-13-6, 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 445-13-6 as follows.

General procedure: A substituted aniline (3.0 mmol) and CDI (3.0 mmol) were dissolvedin anhydrous dichloromethane (15 mL) and the reaction was stirred atroom temperature for 1 h under a nitrogen atmosphere. The solvent wasthen removed under reduced pressure, yielding the crude carbamoylimidazolesas solids. The carbamoylimidazoles were then dissolved indichloromethane (5 mL), and added to a solution of amine 13a or 13b(2.0 mmol) in dichloromethane (15 mL). The reaction was then left tostir for 1 h at room temperature. Dichloromethane (50 mL) was thenadded, and the organic layer was washed with water (3×100 mL). Theorganic layer was dried over Na2SO4 and concentrated under reducedpressure. The product was purified on silica gel by step-wise gradientelution with dichloromethane/ethyl acetate (100:0 to 90:10).

According to the analysis of related databases, 445-13-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Al-Zubaidi, Yassir; Pazderka, Curtis; Koolaji, Nooshin; Rahman, Md Khalilur; Choucair, Hassan; Umashankar, Bala; Bourget, Kirsi; Chen, Yongjuan; Rawling, Tristan; Murray, Michael; European Journal of Pharmaceutical Sciences; vol. 129; (2019); p. 87 – 98;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics