Author: Jessica.F

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. 93-50-5, name is 4-Chloro-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

General procedure: B. To a suspension of compound 7b (1 .69 g, 10.7 mmol, 1 eq) in concentrated HCl (25 mL) and acetic acid (10 mL) at 0 C was added a solution of sodium nitrite (740 mg, 10.7 mmol, 1 eq) in water (10 mL) dropwise. The suspension was warmed to 60 C for 1.5 hrs. The solution was cooled to 0 C and a solution of SnCl2 (5.32 g, 23.6 mmol, 2.2 eq) in concentrated HCl (25 mL) was added. After 30 minutes, a precipatate was collected by filtration to give compound 7c (2.06 g, 93%). 1H NMR (DMSO-d6) delta: 9.94 (br. s., 2H), 7.72 (br. s., 1H), 7.07 (s, 1H), 7.00 (s, 2H). 3.85 (s, 3H). Following the procedure described above for Example 7 and substituting the appropriate reagents, starting materials and purification methods known to those skilled in the art, the following intermediates to compounds of the present invention were prepared:

According to the analysis of related databases, 93-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WINTERS, Michael, P.; SUI, Zhihua; WO2014/28805; (2014); 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. 19230-27-4, name is 1,3-Dibromo-2-chlorobenzene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

1,3-Dibromo-2-Chloro-Benzene 1eq(45.5g), 2-Aminophenylboronic acid 2eq (46.6 g), Tetrakis (triphenylphosphine) palladium (0) (Pd (PPh3) 4), 1-dibromo-2-chloro-5 mol% (9.82 g) and K2CO3 2eq (47.0 g) were suspended in toluene (12 times of solid content, 550 ml) and distilled water (5 times the amount of K2CO3, 235 ml) and refluxed under nitrogen stream for 18 hours. After completion of the reaction, the reaction mixture was extracted with toluene and distilled water. The organic layer was dried over magnesium sulfate (MgSO4), filtered and the filtrate was concentrated under reduced pressure. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and acetone to obtain an intermediate a-1 (37 g, Y = 74%).

The synthetic route of 19230-27-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Jang Gi-po; Kim Jun-seok; Lee Seung-jae; Hong Jin-seok; Kim Chang-u; Jeong Seong-hyeon; Kim Yeong-gwon; Ryu Eun-seon; Jeong Ho-guk; (30 pag.)KR2017/111538; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 6529-53-9, 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. 6529-53-9, name is 1-(2-Bromoethyl)-4-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1.69: Preparation of (4-Bromo-l-methyl-lH-pyrazoI-3-yl)-{4-[2-(4-chloro- phenyl)-ethyl]-piperazin-l-yl}-methanone (Compound 2).A mixture of (4-bromo- 1 -methyl- lH-pyrazol-3 -yl)(piperazin- 1 -yl)methanone hydrochloride (40.0 mg, 0.146 mmol), l-(2-bromoethyl)-4-chlorobenzene (26 muL, 0.18 mumol) and potassium carbonate (61 mg, 0.44 mumol) in acetonitrile (2 mL) was heated at 150 C for 20 min under microwave irradiation in a heavy-walled sealed tube. The reaction mixture was purified by preparative EtaPLC. The corresponding fractions were collected, and lyophilized to afford the TFA salt of the title compound (7.9 mg) as a white solid. Exact mass calculated for C17H20BrClN4O: 410.1; Found: LCMS m/z (%) = 411.1 (M+H+ 79Br, 77%), 413.1 (M+H+ 81Br, 100%).;

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-(2-Bromoethyl)-4-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2008/42388; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 553-82-2,Some common heterocyclic compound, 553-82-2, name is 2,4-Dichloro-1-methoxybenzene, molecular formula is C7H6Cl2O, 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.

2,4-Dichloro-1-methoxybenzene (3.54 g, 20 mmol) was added to a sulfonyl chloride (23.3 g, 200 mmol), and then stirred at 0 C for 2 hr.After the reaction is completed, pour into crushed ice and filter.The collected solid was dissolved in ethyl acetate (100 mL) and dried over anhydrous sodium sulfate.Filtration and concentration gave Compound 19A (3.67 g, 67%)

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

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1871-57-4, These common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 1-3; 1.7 g of methallyl dichloride and 8.9 g of the compound of Formula 11 were put into a reactor, and then 20 mL of tetrahydrofuran was added thereto. To the mixture was added dropwise 0.8 g of sodium hydride. The reactor was kept at 65 0C for 24 hr. 2 mL of water was added dropwise to the reactor. The reaction mixture was evaporated under vacuum to remove the tetrahydrofuran. The concentrate was extracted with 100 mL of diethyl ether and 100 mL of water. The organic layer was subjected to column chromatography using ethyl acetate/methanol (100/0-80/20), giving the compound of Formula 10 in a yield of 28%. 1H NMR (250 MHz, CDCl3): delta 5.18 (s, 2H; CH2), 4.02 (s, 8H; CH2(CH2O)2), 3.62-3.41 (m, 64H; OCH2), 3.37 (s,12H; OCH3), 2.22-2.04 (m, 4H; CH(OCH2)2)

The synthetic route of 1871-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDUSTRY-ACADEMIC COOPERATION FOUNDATION, YONSEI UNIVERSITY; JANG, Woo-Dong; CHOI, Kwang-Mo; WO2010/93128; (2010); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 33050-38-3, 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. 33050-38-3 name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, 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.

General procedure: Appropriate 6-chloro-[1 ,2,4]triazolo[4,3-b]pyridazine (1 eq) or 6-chloro- [1 ,2,4]triazolo[3,4-a]phtalazine (1 eq), potassium carbonate (3 to 4 eq) and the appropriate phenol, thiophenol (1 to 4 eq, 1 eq is preferentially used when R1 = CI) were dissolved in ?,?-dimethylformamide under nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature or at 100-1 10C, or 5-30 minutes at 100-170C on microwave irradiation. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2S04, filtered and evaporated to dryness. The residue was purified by chromatography on silica gel, precipitated, triturated in the appropriate solvent, or used without further purification to obtain the desired 6-aryl-[1 ,2,4]triazolo[4,3-b]pyridazine, or 6-aryl-[1 ,2,4]triazolo[3,4-a]phtalazine.This protocol was used to prepare the following compounds: Cpd.1 -1 , Cpd.1 -3, Cpd.1 -4, Cpd.1 -7, Cpd.1 -8, Cpd.1 -9, Cpd.1 -10, Cpd.1 -1 1 , Cpd.1 -12, Cpd.1 -13, Cpd.1 -14, Cpd.2-1 , Cpd.2-3, Cpd.2-4 and other compounds of the invention that contain a biphenyloxy, a pyridinylphenyloxy, a thiazolylphenyloxy, or a thiopenylphenyloxy group in the 6-substituted position of the [1 ,2,4]triazolo[4,3-b]pyridazines or 6-substituted position of the [1 ,2,4]triazolo[3,4-a]phthalazine (but further information about conditions and purification are reported in Tables of Example 2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; GENFIT; BOUROTTE, Maryline; DELHOMEL, Jean-Francois; DUBERNET, Mathieu; GOUY, Marie-Helene; WO2013/45519; (2013); 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, A new synthetic method of this compound is introduced below., Recommanded Product: 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

99A. Preparation of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine-7-carbaldehyde To a solution of POCl3 (1.24 mL, 13.3 mmol) at 0 C. was added DMF (0.52 mL, 6.6 mmol) and the reaction was stirred until gas evolution subsided. The reaction was then warmed to ambient temperature and 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (250 mg, 1.33 mmol) was added as a solid in one portion. The reaction was warmed to 95 C. and stirred for five hours, then cooled to room temperature. The mixture was poured into ice cold 1:1 saturated aqueous NaHCO3/CH2Cl2 (50 mL). The layers were separated and the aqueous layer extracted with CH2Cl2 (3*25 mL). The combine organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (SiO2,40 g column, 50% CH2Cl2/Hexanes to 75% CH2Cl2/Hexanes, 25 minute gradient) to afford the desired product as a powder (170 mg, 60%). 1H-NMR (DMSO) delta 10.3 (s, 1H), 7.68 (d, 1H, J=4.8 Hz), 7.32 (d, 1H, J=4.8 Hz. HPLC tR=2.35 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm).

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; Bristol-Myers Squibb Company; US2008/45496; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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 1996-30-1, SDS of cas: 1996-30-1

A solution of iso-propylmagnesium chloride in tetrahydrofuran (2M, 106. 6ml) was added dropwise over 15 minutes to a stirred solutionof 2-bromo-4-chloro-1-fluorobenzene (42. 5g) in anhydrous tetrahydrofuran(250ml) at0 C under nitrogen. After a further 15 minutes, a solution ofl-oxa-6-azaspiro [2.5] octane-6-carboxylic acid,1, 1-dimethylethyl ester (43.2g) in anhydrous tetrahydrofuran(50ml) was added followed by copper (I) bromide dimethyl sulphide complex (0.4g). The mixture was stirred at40 C for 18 hours, cooled to20 C, diluted with water(300ml) and extracted with withtert.-butyl methyl ether (2 x300ml). Organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The residual oil was dissolved in 1,2-dimethoxypropane(200ml). Potassium tert-butoxide (22.8g) was added and the mixture stirred at40 C for 16 hours then at50 C for 24 hours. Further potassium tert.- butoxide (5.7g) was added and stirring continued at50 C for 2 hours then at55 C for 4 hours. Water (500ml) was added and the mixture extracted with tert.-butyl methyl ether (2 x300ml). Organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give the sub-title compound (47.45g, 67 %) as an oil. ‘H-NMR (400 MHz,CDC13) :8 1.47 (9h, s), 1.67 (2H, td), 1.85-1. 93 (2H, m), 2.94 (2H, s), 3.39 (2H, td), 3.65-3. 80 (2H,m), 6.67(1H, d), 7.06(1H, d), 7.10(1H, s).

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

Reference:
Patent; ASTRAZENECA AB?; WO2005/49620; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 157590-59-5, The chemical industry reduces the impact on the environment during synthesis 157590-59-5, name is 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

To a solution of Intermediate II (300 mg, 0.887 mmol) and triethylamine (500 mg, 5 mmol) in DMF (5 mL) was added HATU (370 mg, 0.97 mmol) at 0 C. After the mixture was stirred for 15 min, 4-chloro-5-(trifluoromethyl)benzene-l,2-diamine (228 mg, 1.09 mmol) in DMF (1 mL) was added to the reaction. The mixture was allowed to warm to room temperature and stirred for 20hrs. The reaction was diluted with water (50 mL) and the white solid was precipitated. The mixture was filtered and the solid was dried enough under reduced pressure. The solid was dissolved in acetic acid (5 mL) and the mixture was stirred at 85 C for 5hrs. Solvent was removed. The residue was purified by silica gel chromatography (eluted with DCM:MeOH = 50: 1~ 20: 1) to give the title compound (205 mg, 45%) as a light yellow solid. 1H- NMR (400 MHz, DMSO-ifc) delta 10.48 (s, 1H), 7.96 (d, J = 4.1 Hz, 2H), 7.82 (s, 1H), 7.37 (d, J = 2.6 Hz, 1H), 7.07 (d, J = 8.7 Hz, 1H), 7.01 (dd, J = 8.7, 2.6 Hz, 1H), 6.26 (d, J = 5.8 Hz, 1H), 5.42 (d, J = 5.3 Hz, 1H), 3.57 – 3.51 (m, 1H), 2.93 (t, J = 7.7 Hz, 2H), 2.58 – 2.50 (m, 2H), 1.98 (d, J = 2.1 Hz, 1H) ppm. MS: M/e 513 (M+l)+.

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, 4-Chloro-5-(trifluoromethyl)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; WANG, Shaohui; ZHANG, Guoliang; WO2013/97224; (2013); 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. 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, A new synthetic method of this compound is introduced below., Safety of 3-Chloropropan-1-amine hydrochloride

To a solution of phenol D4 (60.0 mg, 0.17 mmol, 1.0equiv) in dry CH3CN (4 mL) was added tetrabutylammonium hydrogen sulfate (16.0 mg, 0.05allowed to stir at room temperature for 30 minutes, at which point 4-(2-chloroethyl)morpholine hydrochloride (63.0 mg, 0.34 mmol, 2.0 equiv) was added to the solution. The mixture was then placed in an oil bath that had been preheated to 55 C, and was allowed to stir at this temperaturefor 14 hours. Following determination of reaction completion by TLC and LCMS analysis, the solution was then removed from the oil bath and allowed to cool to room temperature. Upon cooling, the mixture was diluted with EtOAc (20 mL) prior to the addition of H20 (10 mL), which served to dissolve all of the inorganic solids present. Following separation of the layers, the aqueous layer was extracted with EtOAc (20 mL). The organic layer was then washed withbrine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure.The residue was then purified through flash column chromatography (12 g silica gel cartridge, 0- 50% EtOAc/Hexanes, followed by 0-20% MeOHICH2C12, and desired product eluted during 2%MeOH, to yield the desired product (48.0 mg, 61%) as a light yellow oil. Additionally, at thispoint, the compound appeared to exist as a single diastereomer based on the obtained NIVIR data.?H NMR (400 MHz, CHLOROFORM-d) 7.18 -7.24 (m, 1H), 6.72-6.83 (m, 3H), 4.09-4.14 (m, 2H), 3.71 -3.79 (m, 4H), 2.73 -2.85 (m, 3H), 2.56 -2.65 (m, 4H), 1.89-2.15 (m, 9H), 1.78- 1.87 (m, 5H), 1.65 – 1.75 (m, 6H), 1.56 – 1.65 (m, 1H), 1.32 – 1.44 (m, 1H); ?3C NIVIR (100 IVIFIz, CHLOROFORM-d) 158.8, 147.4, 129.5, 119.4, 113.4, 112.1, 111.4, 109.0, 73.2, 66.9, 65.6, 57.7, 54.1, 42.1, 42.0, 41.3, 36.8, 36.5, 35.8, 34.9, 34.8, 34.3, 32.7, 31.0, 26.9, 26.5, 25.9,23.6; MS (ESI) calculated for C28H40N05 [M + H] m/z 470.29, found 470.22

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; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; TALUKDER, Poulami; RENSLO, Adam, Robert; BLANK, Brian, Richard; MUIR, Ryan, Keith; EVANS, Michael, John; (270 pag.)WO2019/5977; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics