Author: Jessica.F

Reference of 13918-92-8, 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 13918-92-8 as follows.

General procedure: To a solution of 5-bromo-2-methoxypyridin-3-amine (1) (2.01 g,10 mmol) in pyridine (50 ml) at 0 C, 4-fluorophenylsulfonylchloride (2.14 g, 11 mmol) was added. Then the mixture was stirredat room temperature for 24 h. Pyridine was removed underreduced pressure and adding water (100 ml), extracted with ethylacetate (3 100 ml), the organic layer was washed with water(50 ml), dried with Na2SO4 and evaporated to give compound 2a asa white solid (3.22 g, 89.4% yield).

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fan, Yan-Hua; Li, Wei; Liu, Dan-Dan; Bai, Meng-Xuan; Song, Hong-Rui; Xu, Yong-Nan; Lee, SangKook; Zhou, Zhi-Peng; Wang, Jian; Ding, Huai-Wei; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 95 – 106;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 39191-07-6, These common heterocyclic compound, 39191-07-6, name is 1-(3-Chlorophenyl)-N-methylmethanamine, 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.

To a stirred solution of Step 1 intermediate (100 mg, 0.64 mmol) in THF (6.0 mL) at 0C were added triethylamine (195 mg, 1.93 mmol) and 4-nitrobenzoyl chloride (132 mg, 0.70 mmol). The mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with ethyl acetate (100 mL), washed with saturated aqueous sodium bicarbonate solution (20 mL)and saturated ammonium chloride solution (20 mL). The organic layer was washed with water (30 mL) and dried over anhydrous sodium sulfate. The residue thus obtained was purified by silica gel column chromatography to yield 152 mg of titled compound. ?H NMR (300 MHz,DMSO-d6): oe 2.82 (s, 3H), 2.94 (s, 2H), 7.38-7.44 (m, 5H), 7.68-7.77 (m, 3H).

The synthetic route of 39191-07-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (98 pag.)WO2017/199103; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2770-11-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2770-11-8 name is 2-(4-Chlorophenoxy)aniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-[2-(4-Chlorophenoxy)phenylcarbamoyI]piperidine-l-carboxylic acid fer/-butyl ester (AMR01031) C23H27ClN2O4, MW 430,92A solution of piperidine-l,4-dicarboxylic acid mono-tert-butyl ester (AMRO 1030, 417 mg, 1.82 mmol) in dry DCM (8 mL) was stirred under nitrogen, and 4- dimethylaminopyridine (DMPA, 40 mg, 0.327 mmol), (l-(3-dimemylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDC, 1.05 g, 5.46 mmol) and triethylamine (0.25 mL) were added. The resulting mixture was stirred for 30 min under nitrogen and 2-(4-chloro- phenoxy)-phenylamine (AMR01029, 400 mg, 1.82 mmol) in dry DCM (4 mL) was added. After stirring at room temperature for 24 h, the mixture was diluted with DCM, washed EPO with HCl IM (3 x 25 mL), water, saturated NaHCO3 (2 x 25 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated. Flash chromatography on silica gel of the crude product using hexane/EtOAc 8:2 as eluent gave starting material (104 mg). Further elution using hexane/EtOAc 7:3 gave 4-[2-(4-chlorophenoxy)- phenylcarbamoyl]piperidine-l-carboxylic acid tert-butyl ester (430 mg, 55%) as a white solid, mp 97-99 0C. Rf: 0.22 (hexane/EtOAc 7:3) LC/MS (APCI) tr = 3.83 min, m/z 431.23 (33), 429.21 (M’-H,100). 1H NMR (270 MHz, CDCl3) ¡ê 1.44 (9H5 s, 3CH3), 1.68 (2H, m, CH2), 1.83 (2H, m, CH2), 2.36 (IH, tt, J= 11.4, 3.7 Hz), 2.75 (4 H, br t, 2CH2), 4.11 (4H, m, 2CH2), 6.81 (IH, dd, J= 8.2, 1.5 Hz, ArH), 6.93 (2H, AA’BB’, ArH), 7.01 (IH, td, ArH), 7.12 (IH, td, ArH), 7.31 (2H, AA’BB’, ArH), 7.68 (IH, br s, NH) and 8.40 (IH, dd, J= 6.9, 1.5 Hz, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Chlorophenoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
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. 53145-38-3, name is 2-Chloro-6-fluoroanisole, A new synthetic method of this compound is introduced below., Computed Properties of C7H6ClFO

2,6-CFA (10.0 g, 62. 28 mmol) was weighed in a separate flask and transferred to a 3-neck, 500-ml round bottom flask equipped with a thermocouple temperature probe, stir bar, and a N2 inlet. The flask was rinsed with anhydrous DME. Additional DME was added to the reaction flask to give a total DME volume of 106 ml. The reaction was cooled to -78C with a dry ice/acetone bath. Once the reaction reached -77C, ft-BuLi (29 ml, 71.62 mmol, 2.5 M in hexanes) was added slowly, dropwise, using a syringe pump over a 45 minute period. The highest temperature reached during addition was -70.1 C. After complete addition of w-BuLi, the reaction was left to stir for 1 hour at -74.1C. After 1 hour, B(OMe)3 (10.5 ml, 93.42 mmol) was added dropwise using a syringe pump over a period of 22 minutes. The highest temperature reached during the B(OMe)3 addition was -67.0C. After the complete addition of B(OMe)3, the dry ice/acetone bath was removed and the reaction mixture warmed to room temperature (about 23.1 C). Once the reaction mixture reached room temperature, the reaction was left to stir an additional 1 hour at that temperature. This procedure was repeated several times to generate a large amount of PBA-diMe in DME. 244.0 g of PBA-diMe in DME (10.3% PBA basis), 27.82 g of 45% KOH, and 108.70 g of deionized water were added to a one liter flask containing a magnetic stirrer. The one liter flask was cooled with a cold water bath to maintain a temperature of 25C to 30C during the additions. The mixture was stirred for about 2 h and was then vacuum filtered to remove lithium salts. Aqueous and organic phases of the mixture were then separated. Concentrated HC1 (40.48 g) was added to the aqueous phase. The aqueous phase was cooled with a cold water bath during the addition of the HC1 to maintain a temperature of 25C to 30C. The aqueous phase was stirred for about 15 minutes to achieve complete dissolution. MIBK (35.91 g) was added to the aqueous phase and the aqueous phase was stirred for about 15 minutes. An organic phase separated from an aqueous phase to give 127.6 g of the organic phase. Analysis of the organic phase gave 17.57% by weight (89.1% yield) of PBA. The organic phase was concentrated to dryness and then placed in a vacuum oven at 50C to give a white 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; DOW AGROSCIENCES LLC; OPPENHEIMER, Jossian; WO2013/101665; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 15205-15-9 as follows. Computed Properties of C7H7ClFN

Compound 13 was prepared according to the procedure outlined in Scheme 2. The ester was reduced with sodium borohydride (step (a)) and the product alcohol was converted to the corresponding aldehyde utilizing Dess- Martin reagent (step (b)). The aldehyde was condensed with 2-chloro-6- fluorobenzylamine in the presence of anhydrous magnesium sulfate to give an imine, which was subsequently reduced with sodium triacetoxyborohydride to give the secondary amine 13 (step (c)). The imide derivative 16 was also prepared starting with a carboxylic acid which was first converted to the corresponding acid chloride (step (d)). This material was then allowed to react with the anion of 2-chloro-6-fluorobenzamide generated with sodium hydride to give imide 16 in 34% yield (step (e)).

According to the analysis of related databases, 15205-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; TRUSTEES OF BOSTON UNIVERSITY; WO2009/23272; (2009); 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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-4-chloro-2-fluorobenzene

To a stirred and cooled (-78 C) solution of 1-bromo-4-chloro-2-fluorobenzene (1.0 mL, 8.012 mmol) in diethyl ether (10 mL) was added n-BuLi (1.6 M in ether, 5 mL) and stirred for 30 mm. A solution of 1,3-dichloroacetone (1.01 g, 8.012 mmol) in diethyl ether (10 mL) was added to the reaction mixture at -78 C and stirred at -78C to 0 C for lh. To that mixture was added a solution of ferric chloride (26 mg,0.163 mmol) in diethyl ether (5 mL) followed by ethyl magnesium bromide (13.3 mL,40.059 mmol) at 0 C and gradually warmed to RT. The reaction mixture was stirredat RT for 18 h. The reaction mixture was quenched with saturated ammoniumchloride solution (50 mL). The aqueous mixture was extracted with ethyl acetate (2 x100 mL). The combined organic layers were washed with water (100 mL) and driedover anhydrous sodium sulfate. The solution was filtered, concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography to yield 425 mg of the product as a semi-solid. ?H NMR (300 MHz, DMSO-d6) oe 0.96 (d, J = 10.2 Hz, 4H), 6.02 (s, 1H), 7.24 (d, J = 8.7 Hz, 1H), 7.33 (dJ = 9.3 Hz, 1H), 7.51 (t, J = 8.7 Hz, 1H).

According to the analysis of related databases, 1996-29-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin Sundarlal; THOMAS, Abraham; KADAM, Ashok Bhausaheb; DHONE, Sachin Vasantrao; ADIK, Bharat Gangadhar; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; WO2015/159233; (2015); A1;,
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. 67952-93-6, name is 3-Chloro-4-methylbenzylamine, A new synthetic method of this compound is introduced below., Safety of 3-Chloro-4-methylbenzylamine

To a solution of (,S)-3-(5-(aminomethyl)-l-oxoisoindolin-2-yl)azepane- 2,7-dione (TFA salt) (68 mg, 0.176 mmol) in DMF (4 mL) was added CDI (29.0 mg, 0.18 mmol) and the suspension was stirred at RT for 14 h. Then (3-chloro-4-methylphenyl) methanamine (28.0 mg, 0.18 mmol) was added and the mixture was stirred at RT for 8 h. The suspension was diluted with water and extracted with DCM. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give the crude product, which was purified by silica gel chromatography eluting with MeOH/DCM from 0% to 10% to give Compound 18 (21.0 mg, 25.1%) as a white solid. MS (ESI) m/z 469 A [M+H] +. MR (400 MHz, DMSO-de) delta 10.69 (s, 1H), 7.66 (d, J=8 Hz , 1H), 7.46 (s, 1H), 7.38 (d, J=8 Hz, 1H), 7.28 (d, J=7.2 Hz, 2H), 7.11 (d, J=8.8 Hz, 1H), 6.64-6.55 (m, 2H), 5.25-5.21 (m, 1H), 4.49 (s, 2H), 4.34 (d, 7 =6 Hz, 2H), 4.19 (d, 7 =6 Hz, 2H), 3.12-3.04 (m, 1H), 2.57 (d, 7 =16.8 Hz, 1H), 2.28-2.23 (m, 1H), 2.29 (s, 3H), 2.12-1.99 (m, 2H), 1.84-1.81 (m, 1H).

The synthetic route of 67952-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 933190-51-3 as follows. Recommanded Product: 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

Step 3a. Preparation of (6-Chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (214 mg, 921 mumol, Eq: 0.95) and 5-((4-methylpiperazin-1-yl)methyl)pyridin-2-amine (200 mg, 970 mumol, Eq: 1.00) in DMF (10.0 ml) was cooled to 0 C. To this was added sodium hydride (60% in mineral oil, 124 mg, 3.1 mmol, Eq: 3.2). The reaction was allowed to stir at 0 C. for 10 min and then allowed to warm to room temperature and stirred for 72 h. The reaction was quenched with saturated NaHCO3 (aq) and then diluted with water and EtOAc. The organic layer was separated and the aqueous phase was washed with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in Et2O. The organic layer was washed with water and dried over MgSO4. The drying agent was removed by filtration. The resulting solution was concentrated in vacuo to give (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine (170 mg, 49%) as a solid. LC/MS-ESI observed [M+H]+ 358.

According to the analysis of related databases, 933190-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; Brotherton-Pleiss, Christine E.; Lopez-Tapia, Francisco Javier; Lou, Yan; US2013/150360; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, 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 6775-78-6, COA of Formula: C6H4ClN3

Synthesis of 6-chloro-3-iodoimidazo[l , 2-bJpyridazine To a degassed solution of 6-chloroimidazo[l,2-b]pyridazine (1.0 g, 6.51 mmol) and NIS (2.2 g, 9.77 mmol) in MeCN (30 mL) was heated to 60 C for 10 hours. The reaction mixture was cooled to RT and extract with DCM. The organics were washed with Na2S203 (aq), brine and dried over Na2S04. After concentrated, the crude product was purified by column (PE : EA = 5 : 1) to obtain 6-chloro-3-iodoimidazo[l,2-b]pyridazine (1.4 g, yield: 83%). 1H- MR (CDC13, 400 MHz) delta 7.83 (s, 1H), 7.80 (d, J= 4.8 Hz, 1H), 7.04 (d, J= 9.6 Hz, 1H). MS(M+H)+: 280.

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, 6-Chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; HABERMANN, Joerg; KOCH, Uwe; NARJES, Frank; LI, Peng; PENG, Xuanjia; SOLL, Richard; WU, Hao; PALANI, Anandan; DAI, Xing; LIU, Hong; HE, Shuwen; DANG, Qung; WO2013/34048; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 468075-00-5, The chemical industry reduces the impact on the environment during synthesis 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

(Description 25; [L.] [OG,] 3.6mmol) and tri-n-butylvinyl tin (1.21g, 3. [8MMOL)] were dissolved in toluene (20mL) and the solution was degassed for 45 minutes with nitrogen. Tetrakis (triphenylphosphine) palladium [(0)] (lOOmg) was then added and the solution heated at reflux for 2 hours. Once cooled, the solution was concentrated and the residue was purified by silica chromatography to give the title compound [(274MG,] [1.] [2MMOL).] [ON] (360 MHz, [CDCL3)] : 7.40-7. 36 (2H, m), 7.09-7. 01 (2H, m), 5.75 [(1H,] d, J 17.5Hz), 5.47 [(1H,] d, J [10.] 9Hz).

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-chloro-4-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/31190; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics