Tag: M.W=200-300

Synthetic Route of 96558-78-0, 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 96558-78-0 as follows.

3-Bromo-5-chloroaniline (20 g, 96.87 mmol) was added dropwise to 103 N-chlorosuccinimide (12.93 g, 96.87 mmol) in 52 DMF (100 mL) at rt. The resulting solution was stirred at rt for 16 h. The solvent was removed in vacuo. The crude product obtained was purified by flash silica chromatography (5 to 10% 57 EtOAc in 148 petroleum ether) to afford 687 3-bromo-4,5-dichloroaniline (8 g, 34%) as a brown solid; 1H NMR (300 MHz, DMSO, 30 C.) 6.02 (2H, s), 6.83 (1H, d), 6.94 (1H, d); m/z: ES+ [M+H]+=242.

According to the analysis of related databases, 96558-78-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
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Synthetic Route of 56961-77-4,Some common heterocyclic compound, 56961-77-4, name is 1-Bromo-2,3-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.

Under a nitrogen atmosphere, and added at 120 will have the N 1 , the N 1 ,the N 3 – triphenyl benzene-1,3-diamine (20.0g), 1- bromo-2,3-dichlorobenzene ( 6.4g),Pd-132 (0.2g ), NaOtBu (6.8g) and xylene (70ml) was stirred for 2 hours the flask washeated. The reaction mixture was cooled until room temperature, water and ethyl acetateto carry out a liquid. Then, the use of silica gel column chromatography (eluent:toluene / heptane = 4/6 (volume ratio)) to be purified, to thereby obtain the N 1 , theN 1 ‘ – (2- chloro-1,3-phenylene yl) bis (the N 1 , the N 3 , the N 3 – phenyl-trityl-1,3-diamine) (15.0g)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,3-dichlorobenzene, its application will become more common.

Reference:
Patent; Kwansei Gakuin School Corporation; Tian, Shanzuoci; Zhong, Zhongzongyiliang; Zhong, Daoguiyi; Ping, Jingdagui; Xiao, Yeyangping; Zhi, Lianyizhi; Ni, Jingping; Song, Xiawusi; Sheng, Tianlizhao; (405 pag.)CN105431439; (2016); A;,
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Chlorides – an overview | ScienceDirect Topics

Reference of 41965-95-1, 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. 41965-95-1 name is 3-Chloro-4-methoxybenzylamine Hydrochloride, 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.

In THF (150 mL) was suspended 3-chloro-4-methoxybenzylamine hydrochloride salt (16.0 g, 76.9 mmol). The suspension was cooled in an ice bath, and triethylamine (19.4 g, 192.3 mmol) was added dropwisely. The reaction mixture was stirred at ambient temperature for 15 min, then was added ethyl 4-chloro-2-thiomethyl-5-pyrimidine carboxylate (14.9 g, 64.1 mmol). The reaction mixture was stirred at ambient temperature overnight. TLC was used to monitor the reaction. After the completion of the reaction, the solvent was removed by rotary evaporation. Acetic ether (500 mL) and water (200 mL) were added. The organic phase was separated, washed with hydrochloric acid (1N), saturated aqueous solution of sodium bicarbonate and brine, dried over sodium sulfate and filtrated. The filtrate was concentrated under reduced pressure. The solvent was removed by rotary evaporation to give oil. Methanol (100 mL) was added to precipitate a large amount of white solid. The mixture was filtrated and the solid was dried in vacuum to give ethyl 4-((3-chloro-4-methoxybenzyl)amine)-2-thiomethyl-5-pyrimidine carboxylate (21 g, 74.2 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-methoxybenzylamine Hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1996-29-8,Some common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, molecular formula is C6H3BrClF, 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.

n-Butyllithium (2.1 M in hexane; 68 ml, 149 mmol) was added dropwise to a stirred solution of diisopropylamine (15 g, 149 mmol) in anhydrous tetrahydrofuran (700 ml) at -78C under a nitrogen atmosphere. Once the addition was complete the reaction mixture was allowed to warm to 00C, cooled to -78C and a solution of 1-bromo-4- chloro-2-fluorobenzene (25 g, 119 mmol) in anhydrous tetrahydrofuran (60 ml) was added dropwise. The mixture was allowed to warm to -200C, cooled to -78C and a solution of trimethylborate (15 g, 143 mmol) in anhydrous tetrahydrofuran (30 ml) added dropwise. The reaction mixture was allowed to warm to -200C and stirred at that temperature for 30 minutes, then cooled to -78C and peracetic acid (80 ml) added dropwise. The mixture was allowed to warm to ambient temperature and stirred overnight under nitrogen. Water (1 I) was added and the resulting mixture extracted with ethyl acetate (3 x 500 ml). The combined organic extracts were washed with water and brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica using 2% ethyl acetate in hexane as eluent to provide 3-bromo-6-chloro-2-fluorophenol (13.8 g, 51%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-chloro-2-fluorobenzene, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WHITTINGHAM, William Guy; WINN, Caroline Louise; GLITHRO, Harry; ASPINALL, Mary Bernadette; SCREPANTI, Claudio; WO2010/125332; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 115843-99-7, These common heterocyclic compound, 115843-99-7, name is 4-Bromo-3-chloro-2-fluoroaniline, 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 solution of 4-bromo-3-chloro-2-fluoro-aniline (3 g, 13.4 mmol) and HATU (10.2 g, 26.7 mmol) in DMA (30 mL) was added TEA (5.58 mL, 40.1 mmol) and 3-tert-butoxy-3-oxopropanoic acid (3.09 mL, 20.0 mmol) at RT. The mixture was stirred at 50 C for 1 h, diluted with water, and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na 2SO 4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution, 30 – 70% EtOAc/hexane) to give tert-butyl 3-(4-bromo-3-chloro-2-fluoro-anilino)-3-oxo-propanoate (3.35 g).

Statistics shows that 4-Bromo-3-chloro-2-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 115843-99-7.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; OTSUKA PHARMACEUTICAL CO., LTD.; SHIMAMURA, Tadashi; KATO, Ryo; MIURA, Risako; MITA, Takashi; OGAWA, Takahiro; SAGARA, Yufu; JOHNSON, Christopher Norbert; HOWARD, Steven; DAY, James Edward Harvey; ST. DENIS, Jeffrey David; LIEBESCHUETZ, John Walter; (345 pag.)WO2020/22323; (2020); 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. 116369-24-5, name is 4-Bromo-5-chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., Product Details of 116369-24-5

4-bromo-5-chloro-2-fluoroaniline (100mg, 0.446mmol),Isobutyl-1H-pyrazole-4-boronic acid pinacol ester(223 mg, 0.891 mmol),Pd (dppf) Cl2 (163 mg, 0.223 mmol)And potassium carbonate (123 mg, 0.890 mmol) were stirred in 1,4-dioxane / water (10 mL / 2 mL)Under nitrogen atmosphere, the temperature was raised to 110 C for 1 hour under microwave irradiation.Cool to room temperature,add water,Dichloromethane extraction,dry,Purification by column chromatography gave 5-chloro-2-fluoro-4- (1-isobutyl-1H-pyrazol-4-yl) aniline(67.0 mg).

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; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Tong Chaolong; Bao Rudi; Li Yuannian; (67 pag.)CN107312005; (2017); A;,
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Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 210532-25-5, A common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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 25 mL round bottom flask was added 0.10 g (0.35 mmol, 1.0 eq) of JD 1001-002-10 solid, 3.2 mL THF, 0.13 g (1.05 mmol, 3.0 eq) DMAP, 0.22 g (1.05 mmol, 3.0 eq. 3,5-difluorobenzenesulfonyl chloride, the reaction was stirred at room temperature for 3 hours, and the reaction was completed by TLC (developing solvent: PE: EA = 1:1). The organic phase was washed twice with 0.5N aqueous hydrochloric acid and dried over anhydrous sodium sulfateIt was separated and purified by high pressure liquid phase (CH3CN: H2O = 60:40), and lyophilized to obtain 16 mg of JD1001-2064 product in a yield of 9%.

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kunming Jida Pharmaceutical Co., Ltd.; Xiao Xuzhi; Zhang Poyong; Lu Faguan; Wang Zhipeng; Chen Mengran; Guo Kun; Zhou Rui; Zhang Yun; (28 pag.)CN109593061; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2770-11-8, name is 2-(4-Chlorophenoxy)aniline, 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 2770-11-8, Product Details of 2770-11-8

General procedure: To a stirred and cooled solution of 2-(4-chlorophenoxy)aniline (330 mg, 1.50 mmol) and triethylamine (230 muL, 1.65 mmol) in toluene (5 mL), the appropriate acid chloride (pivaloyl chloride, 2,2-dimethylbutyryl chloride, 3-methylbutyryl chloride, propyl chloride, cyclopropanecarbonyl chloride, cyclobutanecarbonyl chloride, methyl succinyl chloride, 4-methoxybenzoyl chloride) (1.65 mmol) was added. Subsequently the reaction mixture was allowed to warm to room temperature. The progress of the reaction was monitored by TLC. After 2-9 h the reaction mixture was extracted with a saturated sodium hydrogen carbonate solution, with a hydrogen chloride solution (10%), with brine and finally with water. Afterwards the organic solution was dried over sodium sulfate and evaporated under reduced pressure. The residue was further purified by recrystallization or column chromatography over silica gel.

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:
Article; Weidner, Thomas; Nasereddin, Abed; Preu, Lutz; Gruenefeld, Johann; Dzikowski, Ron; Kunick, Conrad; Molecules; vol. 21; 2; (2016);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 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.

4-Amino-6-bromo-1H-indole-2-carboxylic acid ethyl ester (200 mg, 0.71 mmol), Pd2 (dba) 3 (64 mg, 0.07 mmol), X-phos (82 mg, 0.14 mmol) and Cs2CO3 ( 684mg, 2.13mmol), 2-chloro-4-bromo-1-fluorobenzene (440mg, 2.13mmol) was added to a microwave tube, toluene (4mL) was added, argon protection, microwave reaction, reaction at 100 C for 4h, the raw materials disappeared. Cool to room temperature, add EA (30mL) to dissolve the residue, wash with saturated brine (20mL ¡Á 3), wash with water (20mL ¡Á 2), column chromatography (P / E = 30: 1 20: 1) to obtain 118mg of pale yellow solid. The yield is 44.55%. Melting point: 220-222 C.

The synthetic route of 60811-21-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1020198-58-6,Some common heterocyclic compound, 1020198-58-6, name is 2-Bromo-1-chloro-3,5-difluorobenzene, molecular formula is C6H2BrClF2, 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. 4-(2-(Benzyloxy)ethyl)-2′-chloro-4′,6′-difluoro-2,3,4,5-tetrahydro-l,r-biphenyl. In a sealed microwave tube, a mixture of 2-{4-[2-(benzyloxy)ethyl]cyclohex-l-en-l-yl}-4, 4,5,5- tetramethyl-l,3,2-dioxaborolane (Intermediate 8, Step 1, 350 mg, 1.02 mmol), [I,G- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (37.4 mg, 0.05 mmol), 2-bromo-l-chloro- 3,5-difluorobenzene (279 mg, 1.23 mmol) and sodium carbonate (1.28 mL, 2 M, 2.56 mmol) in dioxane (5.11 mL) was heated at 70C for 20 hours. Upon completion of the reaction, as determined by LCMS, the reaction mixture was filtered through celite, washed thoroughly with EtOAc, and purified via flash chromatography (silica gel, 0-20% EtO Ac/Heptanes) to provide the title compound as a yellow oil (216 mg, 58.2%). 1H NMR (400 MHz, CDCb) d 7.49 – 7.31 (m, 5H), 6.99 (d, J = 8.3 Hz, 1H), 6.77 (dt, 7 = 2.3, 8.9 Hz, 1H), 5.68 (br s, 1H), 4.59 (s, 2H), 3.63 (t, 7= 6.6 Hz, 2H), 2.48 – 2.13 (m, 3H), 2.02 – 1.84 (m, 3H), 1.82 – 1.68 (m, 2H), 1.59 – 1.40 (m, 1H).

The synthetic route of 1020198-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, THOMPSON, Jillian; BOOKSER, Brett; BURLEY, Scott; GARCIA-REYNAGA, Pablo; HUDSON, Andrew; PETERS, Marco; PRATT, Benjamin; THOMPSON, Aaron; TRAN, Joe; VALDEZ, Lino; (211 pag.)WO2019/168866; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics