Month: July 2021

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. 626-43-7, name is 3,5-Dichloroaniline, A new synthetic method of this compound is introduced below., COA of Formula: C6H5Cl2N

3,5-dichloroanilme ( 1 eq), ethyl 2-bromoacetate (3eq) and NaOAc (3 eq) in EtOH was refiuxed overnight. The solvent was removed under reduced pressure and the residue was extracted with DCM. The orgamc layer was dried over sodium sulfate, concentrated in vacuum, and the residue was purified through Hash chromatography on silica gel eluted with EA-Hexane to give ethyl 2-((3,5-dichlorophenyl)amino)acetate.

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; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1996-29-8, 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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 1-bromo-4-chloro-2-fluorobenzene (5 g, 23.87mmol) in tetrahydrofuran (40 mL) was cooled to -78 C was added LDA, 2M inTHF/heptane/ethylbenzene (14.92 mL, 29.8 mmol) dropwise and the reaction mixture was stirred at this temperature for 30 mm. The solution was allowed to warm to -20 C and stirred for 30 mm. The reaction was cooled to -78 C and trimethyl borate (3.47 mL, 31.0 mmol) dissolved in THF (5 mL) was addeddropwise and the reaction mixture was warmed to -20 C and stirred for 1 h. The reaction mixture was cooled to -78 C and peracetic acid (16 mL, 84 mmol) was added dropwise and the mixture allowed to warm to rt and stirred for 12 h. The reaction mixture was cooled to 0 C and quenched with 5% aqueous ammonium chloride and extracted with ethyl acetate (2X50 mL). The combined organiclayers were washed with brine (50 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure to yield 3-bromo-6-chloro-2- fluorophenol (4.99 g, 18.25 mmol, 76% yield) as yellow oil. LCMS (ESI) m/e 225.1 [(M+H), calcd for C6H4BrC1FO 224.9]; LC/MS retention time (method G): tR = 0.87 mm.

The synthetic route of 1-Bromo-4-chloro-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VRUDHULA, Vivekananda M.; PAN, Senliang; RAJAMANI, Ramkumar; MACOR, John E.; BRONSON, Joanne J.; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; WO2015/38112; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 51419-59-1, These common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, 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.

No. B1-152: N-(1?-Methyl-2?-oxo-1?,2?-dihydrospiro[cyclobutane-1,3?-indol]-5-yl)-1-(4-methylphenyl)methanesulfonamide (0136) (0137) In a round-bottom flask which had been dried by heating, and under argon, 1-methyl-1,3-dihydro-2H-indol-2-one (1.00 g, 7 mmol) and 1,3-dibromopropane (2.06 g, 10 mmol) were dissolved in abs. N,N-dimethylformamide, and the mixture was stirred at room temperature for 5 min. The reaction solution was then cooled to 0° C., and sodium hydride (0.82 g, 20 mmol, 60percent strength dispersion) was then added a little at a time. The resulting reaction mixture was stirred for about 2 h, methanol (4 ml) was then added and after a further 5 min sat. ammonium chloride solution (15 ml) and water (200 ml) were added. The aqueous phase was extracted intensively with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (360 mg, 29percent of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.52 (d, 1H), 7.27 (m, 1H), 7.09 (m, 1H), 6.77 (d, 1H), 3.20 (s, 3H), 2.67 (m, 2H), 2.33 (m, 4H). 1?-Methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (360 mg, 1.92 mmol) was added to conc. acetic acid (5 ml), and fuming nitric acid (0.21 ml, 5.06 mmol) was then added carefully. The resulting reaction mixture was stirred at room temperature for 2 h and then diluted with ice-water. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methyl-5?-nitrospiro[cyclobutane-1,3?-indol]-2?(1?H)-one (380 mg, 85percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.38 (d, 1H), 8.26 (dd, 1H), 6.86 (d, 1H), 3.25 (s, 3H), 2.70 (m, 2H), 2.42 (m, 4H). In the next step, 1?-methyl-5-nitrospiro[cyclobutane-1,3?-indol]-2?(1?H)-one (450 mg, 1.55 mmol) and tin(II) chloride dihydrate (1.40 g, 6.20 mmol) were added together to abs. ethanol and stirred under argon at a temperature of 80° C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5?-amino-1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (230 mg, 66percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 6.98 (d, 1H), 6.62 (m, 2H), 3.14 (s, 3H), 2.64 (m, 2H), 2.38-2.20 (m, 4H). Under argon, 5?-amino-1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (150 mg, 0.79 mmol) and (4-methylphenyl)methanesulfonyl chloride (156 mg, 0.76 mmol) were dissolved in abs. acetonitrile (5 ml) in a round-bottom flask which had been dried by heating, pyridine (0.11 ml, 1.38 mmol) and dimethyl sulfoxide (0.03 ml, 0.42 mmol) were then added and the mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated under reduced pressure, water, dil. hydrochloric acid and dichloromethane were added to the residue that remained and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclobutane-1,3?-indol]-5?-yl)-1-(4-methylphenyl)methanesulfonamide (118 mg, 46percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.29 (m, 3H), 7.16 (d, 1H), 6.96 (br. s, 1H, NH), 6.61 (d, 1H), 4.30 (s, 2H), 3.13 (s, 3H), 2.62 (m, 2H), 2.33 (s, 3H), 2.32-2.17 (m, 4H).

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, Jens; BOJACK, GUIDO; HELMKE, HENDRIK; LEHR, STEFAN; MUELLER, THOMAS; WILLMS, LOTHAR; DITTGEN, JAN; SCHMUTZLER, DIRK; BICKERS, UDO; STREK, HARRY; BALTZ, RACHEL; (88 pag.)US2016/237035; (2016); 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. 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, A new synthetic method of this compound is introduced below., Application In Synthesis of Sodium 4-chlorobenzenesulfinate

To the reactor was added 0.20 mmol of phenacetylene, 0.30 mmol of sodium p-chlorophenylsulfinate,0.40 mmol of ferric chloride hexahydrate, 2.0 mL of trifluoroethanol solvent. Heated to 120 C under a nitrogen atmosphere,After stirring for 3 h, the reaction was stopped, cooled to room temperature, extracted with dichloromethane, dried, and the solvent was removed by distillation under reduced pressure. The crude product was separated by column chromatography to give the desired product in 86% yield.

The synthetic route of 14752-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan University; Yin, Shuangfeng; Ceng, Kui; Chen, Lang; Zhou, Yongbo; (8 pag.)CN106083669; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 115843-99-7, name is 4-Bromo-3-chloro-2-fluoroaniline, molecular formula is C6H4BrClFN, 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. Safety of 4-Bromo-3-chloro-2-fluoroaniline

To a solution of 4-bromo-3-chloro-2-fluoroaniline (25 g, 111 mmol) and di-iso-propylethylamine (48.5 ml, 278 mmol) in DCM (250 mL) cooled in an ice bath was added acetic anhydride (11 .05 ml, 117 mmol)over 1.5 h. The reaction was warmed to RT and stirred for 24 h. The reaction was washed with HCI (1 M, 250 mL), NaHCO3 (150 mL) and water (100 mL). The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient elution, 0-40% EtOAc/petrol) to give the title compound (23.8 g). 1H NMR (500 MHz, DMSO-de) 9.97 (5, 1H), 7.95-7.77 (m, 1H), 7.56 (dd, 1H), 2.10 (5, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 115843-99-7, its application will become more common.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; TAIHO PHARMACEUTICAL CO., LTD.; JOHNSON, Christopher Norbert; BUCK, Ildiko Maria; CHESSARI, Gianni; DAY, James Edward Harvey; FUJIWARA, Hideto; HAMLETT, Christopher Charles Frederick; HISCOCK, Steven Douglas; HOLVEY, Rhian Sara; HOWARD, Steven; LIEBESCHUETZ, John Walter; PALMER, Nicholas John; ST DENIS, Jeffrey David; TWIGG, David Geoffrey; WOODHEAD, Andrew James; (377 pag.)WO2019/167000; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 104-11-0, The chemical industry reduces the impact on the environment during synthesis 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

To a stirred solution of 22 (0.80 g, 5.13 mmol) and K2CO3 (0.95 g, 6.85 mmol) in anhydrous acetonitrile (200 mL) at 0 C, was added crude 21(m) (0.77 g, 3.43 mmol), and the reaction heated and allowed to progress under reflux for 6 h. Acetonitrile was then removed under reduced pressure and the reaction mixture worked up with ethyl acetate (100 mL) and saturated aqueous Na2CO3 (3 × 50 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography using mixtures of ethyl acetate:hexane (5:95) to (20:80) as eluent to give12(m)a as a yellow oil (0.63 g, 61%); 1H NMR (CDCl3, 300 MHz) delta 7.36-7.31 (7H, m, ArH), 7.22 (1H, m, H-3), 4.35 (1H, s, H-1), 3.54 (2H, s, H-8), 3.50 (2H, s, H-10), 2.19 (3H, s, N-CH3); 13C NMR (CDCl3, 75 MHz) delta 139.4 (Arqu), 137.7 (Arqu), 135.3 (Arqu), 132.6 (Arqu), 130.1 (C-12/16), 128.8 (C-13/15), 128.7 (ArC-H), 128.6 (ArC-H), 128.3 (ArC-H), 126.9 (ArC-H), 61.5 (C-8), 61.0 (C-10), 54.7 (C-1), 42.1 (N-CH3); HRMS (ES): Found 301.1221 (M + H)+: C16H18ClN4 (M + H)+ requires 301.1215.

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-(4-Chlorophenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zishiri, Vincent K.; Hunter, Roger; Smith, Peter J.; Taylor, Dale; Summers, Robert; Kirk, Kiaran; Martin, Rowena E.; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 46; 5; (2011); p. 1729 – 1742;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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: 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

EXAMPLE 1N2-((15)-l-cyclohexylethyl)-N4-(3-cyclopropyl-/H-pyrazol-5-yl)pyrrolo[2,l-J] [l,2,4]triazine-2,4-diamineIA. Preparation of 2-chloro-N-(3-cyclopropyl-7H-pyrazol-5-yl)pyrrolo[l,2- f [l,2,4]triazin-4-amine[0078] A solution of 2,4-dichloropyrrolo[l,2-/|[l,2,4]triazine (1.5 g, 5.3 mmol) in z-PrOeta (15 mL) was treated with S-cyclopropyl-iH-pyrazol-S-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold /-PrOH and dried under vacuum to afford IA as a solid (1.3 g, 90%). HPLC tR = 3.301 min (YMC S5 Combiscreen ODS 4.6 x 50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+ = 275.37 ‘. EXAMPLE 43 2-((4-((3-cyclopropyl-lH-pyrazol-5-yl)amino)pyrrolo[2,l-/| [l,2,4]triazin-2- yl)amino)-N-l,3-thiazol-2-ylacetamide43 A. Preparation of 2-chloro-N-(3-cyclopropyl-7H-pyrazol-5-yl)pyrrolo [1,2- /][l,2,4]triazin-4-amine [0085] A solution of 2,4-dichloropyrrolo[l,2-/|[l,2,4]triazine (1.5 g, 5.3 mmol) in i-PrOH (15 mL) was treated with S-cyclopropyl-iH-pyrazol-S-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold i-PrOeta and dried under vacuum to afford 43A as a solid (1.3 g, 90%). etaPLC tR = 3.301 min (YMC S5 Combiscreen ODS 4.6 x 50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+ = 275.37.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/21859; (2008); 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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6BrClO

Step 2 Preparation of 3-chloro-4-methoxyphenylboronic acid Following the general procedure outlined in Synthetic Scheme I, 10.2 g (46.2 mmol) of 4-bromo-2-chloroanisole (Step 1) was converted to 3-chloro-4-methoxyphenylboronic acid: NMR (CDCl3) delta 3.83 (s, 3H), 6.57 (s, 2H), 6.83 (d, J=8 Hz, 1H), 7.64 (dd, J=1.5, 8 Hz, 1H), 7.77 (d, J=1.5 Hz, 1H).

According to the analysis of related databases, 50638-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; G.D. Searle & Co.; US5739166; (1998); A;,
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 10061-02-6 as follows. SDS of cas: 10061-02-6

Example 15: N-((S)-2-Amino-l-hydroxycarbamoyl-2-methyl-propyl)-4-((E)-7-hydroxy- hept-2-en-4-ynyIoxy)-benzamide (Compound 15); 15Step 15-A:To a solution of trans- 1,3 -dichloropropene (2.19 g, 19.7 mmol), potassium carbonate (3.63 g, 26.3 mmol), and potassium iodide (0.109 g, 0.657 mmol) in acetonitrile (200 mL) was added methyl-4-hydroxybenzoate (2.0 g, 13.2 mmol). The reaction was stirred at 80 0C for 4 hr after which it is quenched with brine, extracted with ethyl acetate, and washed with water. Organic phase dried with anhydrous magnesium sulfate, filtered, concentrated followed by purification with silica-gel chromatography (0-50% Ethyl Acetate/Heptane) to afford 15b (2.77 g). Found m/z ES+ = 227.

According to the analysis of related databases, 10061-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; DOBLER, Markus, Rolf; LENOIR, Francois; PARKER, David, Thomas; PENG, Yunshan; PIIZZI, Grazia; WATTANASIN, Sompong; WO2010/31750; (2010); 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. 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, A new synthetic method of this compound is introduced below., Recommanded Product: 13745-86-3

The typical procedure for the iron-catalyzed cross-coupling reaction of imidoyl chlorides with alkylmagnesium halide was applied to form the title compound and the following reagents were employed: ll-chloro-dibenzo[b,fj[l,4]thiazepine ( 49 mg, 0.20 mmol), Fe(acac)3 (3.53 mg, 0.001 mmol), THF (2 mL) and N-methylpyrrolidone (0.2 mL), cyclohexyl magnesium chloride (2 M in Et2O, 0.20 mL, 0.40 mmol). Purification by flash chromatography (ethyl acetate/heptane 1:4) afforded 51.9 mg (89%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): delta 7.45-7.43 (IH, m), 7.04-7.36 (2H, m), 7.33-7.21 (4H, m), 7.16 (IH, d, J = 8.0, 1.6Hz), 7.02-6.98 (IH, m), 2.86 (IH, tt, J = 11.2, 3.2Hz), 2.19-2.15 (IH, m), 1.96-1.92 (IH, m), 1.86-1.70 (4H, m), 1.45-1.26 (4H, m).I3C NMR (100 MHz, CDCl3): delta 176.7, 149.0, 141.2, 139.4, 132.4, 131.8, 130.2, 129.1, 128.9, 128.5, 127.4, 125.4, 125.1, 49.1, 32.6, 30.2, 27.0, 26.4, 26.2.

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; ACADIA PHARMACEUTICALS INC.; WO2007/47776; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics