Tag: M.W=200-300

19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, 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. SDS of cas: 19752-55-7

Magnesium turning (2.8 g) and iodine (50 mg) were added to a 250 mL three-necked round bottom flask and stirred under an argon atmosphere for 30 minutes. 1-bromo-3,5-dichlorobenzene (20.7 g) dissolved in tetrahydrofuran was slowly added dropwise, heated to reflux for 2 hours, and then cooled to room temperature. In another round bottom flask, trimethoxyboraine (33.8 mL) was dissolved in 80 mL of diethyl ether. After cooling to -15 C, a previously prepared Grignard reagent was added dropwise through a cannula. Slowly raised to room temperature and stirred for 12 hours. The resulting white solid was washed with pentane and the filtrate was concentrated under reduced pressure to give 14.6 g of the title compound.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dae Joo Electronic Materials Co., Ltd.; Jeon Yeong-min; Park Jeong-gyu; Lee Hyeon-seok; Kim Min-yeong; (50 pag.)KR2019/106313; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 38762-41-3, 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. 38762-41-3 name is 4-Bromo-2-chloroaniline, 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.

Synthesis of methyl 4?-amino-3 ?-chlorobiphenyl-4-carboxylate (65): A mixture of 4-bromo-2-chloroaniline (10 g, 48.5 mmol), 4-(methoxycarbonyl)phenylboronic acid (9.6 g,53.4 mmol), Pd(dppf)C12 (3.6 g, 4.85 mmol) and K2C03 (13.4 g, 97 mmol) in dioxane (100 mL) and water (10 mL) was degassed and heated at 100C for 2 h. After cooling down to room temperature, the reaction mixture was poured into water, extracted with EtOAc (100 mL X 3). The combined organic solvents were dried over anhydrous Na2504, concentrated under reduced pressure and purified by silica gel chromatography (10-50% EtOAc/petroleum ether) to give 11 g of methyl 4?-amino-3?-chlorobiphenyl-4-carboxylate 65 as black solid (86% yield). LCMS: m/z 262.1 [M+H], , tR= 1.98 min

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

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; (153 pag.)WO2017/31213; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1298031-94-3, A common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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.

8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1.0 g, 4.0 mmol) was combined with K2C03 (1.1 g, 8 mmol) and phenol (0.6 g, 6.0 mmol) in NMP (10 mL). The mixture was stirred at 60 C for 16 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-30% EtOAc in petroleum ether to yield 6-chloro-2- methyl-8-phenoxyimidazo[l,2-b]pyridazine (560 mg, 53%). MS m/z 260.0, 262.0 [M+H]+.

The synthetic route of 1298031-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); 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. 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below., Formula: C6H3BrClN3

A solution of 6-(trifluoromethyl)pyridin-2-amine (0.668 g, 4.12 mmol) in DMF (5 mL) was added NaH (0.10 g, 4.18 mmol) and stirred for 0.5 h. To the mixture was added 8-bromo-6- chloroimidazo[l,2-b]pyridazine (0.38 g, 1.65 mmol) under N2. The mixture was stirred at room temperature for 16 h then 100 mL of water was added and the precipitate collected by filtration and washed with water to give 6-chloro-N-(6-(trifluoromethyl)pyridin-2-yl)imidazo[l,2- b]pyridazin-8-amine (0.513 g, 99 %) as a light brown solid. LC-MS: [M+H]+, 314.1 , tR = 1.738 min.

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; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); 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. 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 11-Chlorodibenzo[b,f][1,4]thiazepine

EXAMPLE 2; Preparation of ll-piperazinyldibenzo[b,f][l,4]thiazepine; [0035] To the organic fraction recovered according to Example 1, 140 g (1.6 moles) of anhydrous piperazine is added in a reaction vessel. The temperature of the mixture is gradually increased to reflux (about 110 0C) over a period of about one hour and is kept at that temperature for about 1 to 2 hours. The heat-up is aided by the exothermic reaction that occurs. The extent of the reaction can be monitored by HPLC, but is typically completed within three hours. The reaction mixture then is cooled to ambient temperature and precipitated piperazine dihydrochloride is filtered from the product solution. An aqueous solution of MTBE and methanol (water:MTBE:methanol having a volume ratio of 2.5:1:0.6) is used to wash excess piperazine from the solution, which is removed with the aqueous phase that separates from the organic phase on standing. The organic layer can be washed one to two additional times with water.

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 13745-86-3.

Reference:
Patent; CAMBREX CHARLES CITY, INC.; WO2006/135544; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, 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 1996-29-8, 1996-29-8

EXAMPLE 13 (3R,4S)-4-(4′-Chloro-2′-fluorobiphenyl-4-yloxy)-1-pyridin-3-yl-pentan-3-ol Prepared according to the method described in Example 12b) from (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid (0.20 g, Example 11)), 1-bromo-4-chloro-2-fluorobenzene (0.21 g), 2M aqueous sodium carbonate (0.57 ml) and tetrakis(triphenylphosphine)palladium (0) (0.1 g) in toluene (5 ml) and ethanol (2 ml). The reaction mixture was heated at 100 C. for 4 hours. After cooling, the solution was concentrated under reduced pressure. Concentrated hydrochloric acid (1 ml) was added to a solution of the residue in methanol (5 ml) and the suspension was stirred at room temperature for 6 hours. After work up, the residue was purified by normal-phase HPLC eluding with a gradient of 0-25% ethanol in dichloromethane to give an oil (0.13 g). MS (APCI) 386 (M+H)+ 1H-NMR(CDCl3) 8.51(1H,d); 8.45(1H,dd); 7.56-7.54(1H,m); 7.43(2H,dd); 7.33(1H,t); 7.26-7.15(3H,m); 6.94(2H,d); 4.41-4.37(1H,m); 3.87-3.86(1H,m); 3.0-2.95(1H,m); 2,80-2.75(1H,m); 2.15(1H,d); 1.87-1.84(2H,m); 1.31 (3H,d).

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-Bromo-4-chloro-2-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US6300352; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13526-66-4, These common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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.

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1 ,2-6]pyridazine were suspended in 508 mL 1 ,4-dioxane. 10, 1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(triphenylphosphino)palladium-(0) and 19.0 g (179 mmol) sodium carbonate were added. The obtained mixture was heated to 100 C for 24 h.400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichioromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. 1H-NMR (300 MHz, DM50-d6): delta [ppm]= 7.23 – 7.40 (m, 2H), 7.51 (d, 1 H), 7.59 – 7.67 (m, 2H), 7.77 (d, 1 H), 8.33 – 8.40 (m, 2H).LCM5 (Method 1 ): Rt = 1 .35 min; MS (ESIpos) m/z = 270 [M+H]

Statistics shows that 3-Bromo-6-chloroimidazo[1,2-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 13526-66-4.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; KNUT, Eis; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark; BOeMER, Ulf; GUeNTHER, Judith; FANGHAeNEL, Joerg; KORR, Daniel; WO2012/163942; (2012); 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 38762-41-3 as follows. Recommanded Product: 4-Bromo-2-chloroaniline

Preparation 94: 2-Chloro-4-(oxazol-5-yl)aniline; [00264] Palladium acetate (5.4mg, 0.024mmol) was added to a solution of 4-bromo-2- chloroaniline (0.1 g, 0.484mmol), oxazole (0.064mL, 0.969mmol), di(1 -adamantyl)-/> butylphosphine (0.017g, 0.048mmol), pivalic acid (0.020g, 0.194mmol) and potassium carbonate (0.201 g, 1 .453mmol) in DMA (2.4ml_). The reaction mixture was heated at 1 10 C overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35mg, 37%). 1 H NMR (500 MHz, CDCI3): delta 4.25 (br s, 2H), 6.82 (d, J = 8.3Hz, 1 H), 7.20 (s, 1 H), 7.38 (dd, J = 8.3, 2.0Hz, 1 H), 7.58 (d, J = 2.0Hz, 1 H), 7.87 (s, 1 H).LC (Method B)-MS (ESI, m/z) fR 2.47 min, 195 [(M+H+), 100%].

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); 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. 766545-20-4, name is 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride

Preparation 26 2-Amino-1-(7w8-dihydro-5H-r1, 61naphthvridin-6-yl)-ethanone; Step A A solution of 90 mg of 2-chloro-5, 6,7, 8-tetrahydro- [1, 6] naphthyridine hydrochloride (U. S. Pat. No. 6,169, 093), 0.134 g of N-carbobenzyloxyglycine, 0.130 g of triethylamine, and 0.087 g of 1-hydroxy-7-azabenzotriazole in DMF (2.7 mL) at 0 C was stirred as 0.123 g (0.640 mmol) of EDC was added. After two h, the reaction mixture was poured into 4% magnesium sulfate solution, and the resulting solution was extracted with EtOAc and then methylene chloride. The organic extracts were dried over sodium sulfate, filtered, and concentrated to give an oil that solidified upon standing. Trituration with MeOH and collection of the solids provided the desired amide intermediate.

The synthetic route of 766545-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/35532; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6529-53-9, The chemical industry reduces the impact on the environment during synthesis 6529-53-9, name is 1-(2-Bromoethyl)-4-chlorobenzene, I believe this compound will play a more active role in future production and life.

Example 1.49: Preparation of (4-Chloro-l-methyl-lH-pyrazol-3-yl)-{4-[2-(4- chlorophenyl)-ethyl]-piperazin-l-yl}-methanone (Compound 44). In a heavy-walled sealed tube, (4-chloro-l-methyl-lH-pyrazol-3-yl)(piperazin-l- yl)methanone dihydrochloride (27 mg, 0.10 mmol) was dissolved in DMF (1.0 mL). 4- Chlorophenethyl bromide (12 mg, 0.083 mmol) and potassium carbonate (35 mg, 2.5 mmol) were added. The reaction was heated under microwave irradiation for 10 min at 100 C. The solids were filtered and the filtrate was purified by preparative HPLC. The best fractions were lyophilized to afford the TFA salt of the title compound (15 mg) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 2.96-3.03 (m, 2H), 3.03-3.28 (m, 2H), 3.30-3.75 (m, 6H), 3.87 (s 3H), 4.23-4.40 (bs, IH), 4.46-4.65 (bs, IH), 7.32 (d, J = 8.4 Hz, 2H), 7.43 (d, J = 8.3 Hz, 2H), 8.10 (s, IH). Exact mass calculated for Ci7H20Cl2N4O: 366.1; Found: LCMS m/z (%) = 367.4 (M+H+ 35Cl, 100%), 369.4 (M+H+ 37Cl, 64%).

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