Tag: M.W=200-300

A common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, molecular formula is C12H10ClNO, 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. 2770-11-8.

Preparation of l-(4-(2-(4-chIorophenoxy)phenylamino)azepan-l-yI)ethanoneSTX1762 C20H23ClN2O2, MW: 358.86To a solution of 2-(4-chlorophenoxy)phenylamine (113 mg, 0.51 mmol), 1-acetylazepan-4-one (159 mg, 1.02 mmol) and acetic acid (153 mg, 2.55 mmol) in DCE (4 ml), was added sodium triacetoxyborohydride (270 mg, 1.28 mmol). The reaction mixture was allowed to stir at room temperature for 10 days. On return, the reaction was quenched with saturated aqueous sodium sodium bicarbonateonate (15 ml) and extracted with ethyl acetate (2 x 15 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography then proceeded (eluent; 9:1 hexane:ethyl acetate to ethyl acetate) to afford the title compound as a pale yellow oil (67.1 mg, 37%).1H NMR (270 MHz, CDCl3): delta 1.49-2.27 (9H, m, 3 x CH2, CH3), 3.30- 3.72 (5H, m, 5 x CH), 4.10 (IH, br s, NH), 6.59-6.67 (2H, m, Ar-H), 6.78-6.89 (3H, m, Ar-H), 7.00-7.08 (IH, m, Ar-H), 7.21-7.24 ppm (2H, m, Ar-H). 13C NMR (67.93 MHz, CDC13): delta 21.9, 24.2, 25.3, 32.8, 33.0, 34.2, 35.2, 42.0, 45.0, 45.1, 48.3, 51.0, 52.0, 112.2, 118.6, 118.7, 125.4, 129.7, 129.8, 139.0, 142.8, 156.1, 156.2, 170.5 ppm. LCMS: EPO M+U: 359.45 HPLC: 95.92% (2.677 min, isocratic 90% acetonitrile, 10% water at 1 ml/min).

The synthetic route of 2-(4-Chlorophenoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
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A common compound: 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1996-29-8

In a 200 mL three-necked flask, the obtained white solid and 4.2 g (20 mmol) of 1-bromo-4-chloro-2-fluorobenzene, 6.1 g (19 mmol) of cesium carbonate were placed. To this mixture, 30 mL of N-methyl-2-pyrrolidone was added and the mixture was degassed by stirring while reducing the pressure. After degassing, the mixture was stirred at 120 C. for 7 hours under a nitrogen stream. After stirring, water was added to this mixture, and after ultrasonic irradiation, filtration was carried out to obtain a solid. The obtained solid was washed with water and ethanol. This solid was purified by silica gel column chromatography (developing solvent: toluene). The obtained solid was recrystallized from toluene / ethyl acetate to obtain 1.9 g of a white solid in a yield of 42%. The synthesis scheme of Step 2 is shown below.

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, 1996-29-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Semiconductor Energy Laboratory Ltd.; Takeda, Kyoko; Ozaka, Harue; Seo, Tetsushi; Suzuki Tsune Toku; Hashimoto Naoaki; Takida Yuu Kai; (218 pag.)JP6339749; (2018); B1;,
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60811-21-4, These common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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 21 6(3-Chloro-4-fluoro-phenyl)-4-isopropyl-3,4-dihydro-1H-quinoxalin-2-one A mixture of (3,4-dihydro-4-isopropyl-2-oxoquinoxalin-6-yl)boronic acid (2.4 g, 10 mmol), 4-bromo-2-chlorofluorobenzene (2 g, 10 mmol), potassium carbonate (4 g, 30 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.46 g, 0.4 mmol) in dimethoxyethane (100 ml), ethanol (25 ml) and water (25 mol) was heated to reflux for 6 hrs. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate (3*). The combined organic layers were washed with water, then brine, dried (MgSO4) and evaporated to obtain crude product (2.9 g, 91%). Recrystallization from EtOAc/hexane afforded the title compound, mp 208-213 C.: 1H-NMR (DMSO-d6) delta 1.16 (d, J=6.59 Hz, 6H), 3.56 (s, 2H), 4.22 (septet, J=6.59 Hz, 1H), 6.86 (d, J=7.91 Hz, 1H), 6.96 (dd, J=7.91, 1.76 Hz, 1H), 7.01 (d, J=1.76 Hz, 1H), 7.43 (t, J=9.01 Hz, 1H), 7.61 (m, 1H), 7.82 (dd, J=7.14, 2.31 Hz, 1H), 10.47 (s, 1H). MS (EI) m/z 318 [M]++ 1 chlorine.

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 60811-21-4.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceutical, Inc.; US6423699; (2002); B1;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 1435-50-3, name is 2-Bromo-1,4-dichlorobenzene, molecular formula is C6H3BrCl2, 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. 1435-50-3

After 1-bromo-2,5-dichlorobenzene (15.6 g, 69.1 mmol) and 2-formylphenylboronic acid (11.4 g, 76 mmol) were dissolved in tetrahydrofuran (THF) (200 mL), 2M potassium carbonate aqueous solution (70 mL) was added thereto, and tetrakistriphenylphosphino palladium (Pd(PPh3)4 (1.6 g, 2 mol%) was put thereinto, agitated and refluxed for 5 hours. The temperature was lowered to normal temperature, the water layer was removed, and the organic layer was dried with anhydrous magnesium sulfate (MgS04) and filtered. The filtered solution was concentrated under the reduced pressure, and columned with tetrahydrofuran:hexane = 1:10 to prepare the compound A-1 (13.9 g, 80%), MS: [M+H]+=251

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1435-50-3, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; EP2311826; (2011); A2;,
Chloride – Wikipedia,
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202197-26-0, Name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 202197-26-0, 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.

3-Chloro-4-((3-fluorobenzyl)oxy)aniline (12.58 g, 50 mmol) was added to 100 ml of benzene and stirred well.0.4 g of acetic acid (as a catalyst) was added, followed by dropwise addition of trimethyl orthoformate (2.65 g, 25 mmol) with an addition funnel at room temperature.After the completion of the dropwise addition, the Dean-Stark apparatus was installed, and the reaction mixture was placed in an oil bath and heated to 80 C for 1 hour.The Dean-Stark device collects ethanol; then the temperature is raised to 110 C for 2 h, after the reaction is finished, it is cooled to room temperature and placed in an ice bath.The solid was filtered, and the filter cake was washed with a little toluene to give (E)-N’-(3-chloro-4-((3-chlorobenzyl)oxy)phenyl)-N-(3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)carboxamidine 11.9 g, yield 89.9%.

Statistics shows that 3-Chloro-4-((3-fluorobenzyl)oxy)aniline is playing an increasingly important role. we look forward to future research findings about 202197-26-0.

Reference:
Patent; Yancheng Normal College; Nanjing University Of Technology Dafeng Ocean Industrial Institute; Sun Yaquan; Zong Chaoyang; Gu Huiwen; (10 pag.)CN108440420; (2018); A;,
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The chemical industry reduces the impact on the environment during synthesis 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, I believe this compound will play a more active role in future production and life. 1127-85-1

to stire solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (6.46g, 18.8 mmol) in THF(5 mL) was added (rac)-(28,38)-methyl 3-aminobicyclo[2.2.2]octane-2-carboxylate (1.99 g,20 10.8 mmol) and DIPEA (4.2 g, 5.68 mL, 32.5 mmol) and the resulting reaction mixturesolution was stirred at 70 oc for 12 h. After cooling to room temperature, the reactionmixture was poured into water (1 00 mL) and extracted with EtOAc (150 mL twice). Thecombined organic layers were washed with brine, dried over anhydrous Na2804 , filteredand concentrated in vacuo to give a crude product, which was purified by silica gel flash chomatography (0-40% EtOAc-hexane gradient) to afford the title compound ( 1 g, 26.4%yield) as white foam. MS: 350.1 [M+Ht

The chemical industry reduces the impact on the environment during synthesis 1127-85-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; TAN, Xuefei; ZBINDEN, Katrin Groebke; KUHN, Bernd; WANG, Lisha; LIU, Yongfu; WU, Jun; SHEN, Hong; SHI, Tianlai; (174 pag.)WO2017/133664; (2017); 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. 60811-18-9, name is 4-Bromo-1-chloro-2-fluorobenzene, A new synthetic method of this compound is introduced below., 60811-18-9

(5) Metal magnesium in an amount of 1.2 g was suspended in 20 ml of THF under nitrogen gas stream, and a solution prepared by dissolving 9.6 g of 3-fluoro-4-chloro-bromobenzene in 50 ml of THF was added dropwise thereto and stirred at room temperature for 1 hour to prepare a solution of Grignard reagent. In 30 ml of THF was dissolved 9.7 g of the 4-(trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)iodobenzene mentioned above, 1 g of palladium chloride was added thereto, and they were stirred under a reflux. The Grignard reagent prepared by the procedures mentioned above was added dropwise thereto and they were reacted while stirring for 2 hours. Reaction solution thus obtained was added to 100 ml of dilute hydrochloric acid and the product was extracted with 100 ml of heptane. Organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under a reduced pressure to obtain a yellow-brown oily product. This product was purified by a column chromatography over an alumina by using heptane as an eluent. Further, the product was recrystallized from heptane to obtain 2.3 g of the subject compound. CN 138.1, NI 227.7 According to the procedures mentioned above, following Compounds No. 2 to No. 63 were synthesised:

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; Chisso Corporation; US5858275; (1999); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 54932-72-8

Nitrogen gas was purged through a stirred solution of 5-bromo-2-chiorotoluene (452 muIota, 3.41 mmol) in 1 ,4-dioxane (15 ml) for 30 mins. 2,2′-Bis(diphenylphosphino)-1 , 1 ‘- binaphthyl (212 mg, 0.34 mmol), Pd(OAc)2 (153 mg, 0.68 mmol) and Cs2C03 (2.22 g, 6.81 mmol) were then added. The stirred solution was then purged of nitrogen for a further 30 min after which 1-Boc-3-aminopyrrolidine (745 muIota, 4.09 mmol) was added and solution stirred at reflux for 48 h under N2. The solvent was then evaporated in vacuo and the crude residue dissolved in EtOAc (40 ml) which was then washed with water (2 x 30 ml), brine (2 chi 30 ml), dried with Na2S04, filtered and concentrated. The crude residue was then purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain WIN-321 -142-01 as a solid (111 mg, 10.4%).1H NMR (CDCI3): delta 7.13 (d, J 8.4 Hz, 1H), 6.48 (d, J 2.6 Hz, 1H), 6.39 (dd, J 8.58, 2.86 Hz, 1H), 3.99 (br. s., 1H), 3.79-3.57 (m, 2H), 3.56-3.38 (m, 2H), 3.31 -3.14 (m, 1H), 2.30 (s, 3H), 2.10 – 2.26 (m, 1 H), 1.96 – 1.79 (m, 1 H), 1.47 (s, 9H). MS, m/z = 255 (100) [M-56], 257 (30).

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, 54932-72-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF MELBOURNE; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; SLEEBS, Brad; PURCELL, Damian Francis John; JACOBSON, Jonathan; LEWIN, Sharon; NGUYEN, William; (163 pag.)WO2017/219083; (2017); 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. 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., 54932-72-8

a. 4-(4-chloro-3-methylphenyl)-1-methyl-1H-pyrazole A mixture of 2-chloro-5-bromotoluene (305 mg, 1.48 mmol), 1-methylpyrazole-4-boronic acid pinacol ester (315 mg, 1.51 mmol), Pd(dppf)Cl2 (130 mg, 0.16 mmol), and K2CO3 (400 mg, 2.89 mmol) in a mixture of THF (4 mL) and water (1.2 mL) was heated at 120 C. for 1 h under microwave irradiation. The reaction mixture was concentrated in vacuo and purified by Biotage (SNAP 25 g column, cyclohexane/EtOAc 90/10->50/50) to give the title compound as a brown oil (215 mg, 70%).

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; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common compound: 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 54932-72-8

General procedure: Nitrogen was purged through a stirred solution of 4-bromo-1-chloro-2-methylbenzene (258muL, 1.95mmol) in 1,4-dioxane (5mL) for 30min rac-BINAP (363mg, 1.95mmol), caesium carbonate (1.27g, 3.89mmol), 1-Boc-piperazine (363mg, 1.95mmol) and Pd(OAc)2 (87mg, 0.039mumol) and stirred at reflux for 14h under N2. The reaction was filtered through celite and concentrated in vacuo. The residue was dissolved in EtOAc (20mL), filtered through celite and washed with additional EtOAc (50mL). The organic layer was washed with water (2¡Á20mL) and brine (2¡Á20mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain the protected intermediate as a solid (413mg, 68%). MS, m/z=255 (100) [M-tBu]. The intermediate was dissolved in a 1:3 mixture of TFA/DCM (4mL) and stirred at 20C for 1h. The solvent was evaporated in vacuo and the crude residue dissolved in EtOAc (10mL) which was successively washed with a 10% solution of NaHCO3 (10mL), water (10mL) and brine (10mL). The organic layer dried with Na2SO4 and concentrated in vacuo to obtain 92 as a solid (211mg, 76%). 1H NMR (300MHz; CDCl3): delta 7.23 (d, J 8.8Hz, 1H), 6.80 (d, J 2.9Hz, 1H), 6.71 (dd, J 3.0, 8.7Hz, 1H), 3.35-3.19 (m, 8H), 2.35 (s, 3H). MS, m/z=211 (100) [M+H]+, 213 (30).

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, 54932-72-8, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Blackmore, Timothy R.; Jacobson, Jonathan; Jarman, Kate E.; Lewin, Sharon R.; Nguyen, William; Purcell, Damian F.; Sabroux, Helene Jousset; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 195; (2020);,
Chloride – Wikipedia,
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